Events in Anne Arundel County, MD

● Listings verified — Wednesday, October 14 · every listing checked against its source by our Anne Arundel County editors

59This week
152Next 30 days
6Free this week
104Venues tracked

This weekend in Anne Arundel County

The ones worth planning around. All 27 weekend events →

Meet and Ride

Sat, Oct 17 · 9:30am · Chesapeake Cycles, Annapolis

Free events in Anne Arundel County

6 of this week's 59 events cost nothing. See all 6 free events →

  • Wed 7:30pm

    Trivia Night | Dave & Buster's - Hanover MD - WED 730p - @LeaderboardGames

    Dave & Buster's (Hanover, MD), 7000 Arundel Mills Cir, Hanover · verified Oct 11
    Free

    Test your knowledge at a fast-paced trivia night at Dave & Buster's in Hanover, MD. Play a live hosted, competitive game that features a mix of question styles, including an image round and a music round. Use your phone to submit answers, track your standing on the leaderboard, and rack up points. Teams of up to six can collaborate on questions spanning pop culture, sports, history, science, and more. It is free to play, and prizes are awarded to the winners.

    Event website ↗
  • Sat 11am

    FREE Family Event: Harvest Fest

    600 N Bestgate Rd, Annapolis · verified Oct 11
    Free

    A family friendly afternoon features complimentary food, fair style games, a petting zoo, axe throwing, face painting, and other activities. A cake walk adds to the fun with a chance to win a homemade dessert to take home.

    Event website ↗
  • Sat 12pm

    Howl-o-Ween Adoption Event at Petco Severna Park

    Petco (571 Ritchie Hwy, Severna Park, MD), 545 Governor Ritchie Hwy, Severna Park · verified Oct 11
    Free

    Celebrate the season at a Howl-o-Ween adoption event hosted at Petco Severna Park. The BFF Waggin' will attend with adoptable dogs and cats looking for loving homes. Fees for adoptions completed at the event are waived, and standard adoption procedures still apply. Expect a cheerful Halloween atmosphere and plenty of chances to meet a new companion.

    Event website ↗
  • Sat 4pm

    Mascot Visit at sweetFrog Laurel

    3341 Corridor Marketplace, Laurel · verified Oct 11
    Free

    At sweetFrog Laurel, guests can meet one of the sweetFrog mascots, Scoop or Cookie, during a special appearance. There will be opportunities for photos and lighthearted fun, making it easy to bring home a memory with these characters. Free tickets are available to confirm attendance.

    Event website ↗

Live music in Anne Arundel County

14 shows this week — see the full live-music calendar →

  • Wed 5:30pm

    Sparks Solo

    Nonna Angela's Italian Bistro & Wine Bar, 2225 Defense Hwy, Crofton
    See details

    Sparks presents a monthly solo performance at a traditional style Italian bistro and wine bar.

    Event website ↗
  • Wed 6:30pm

    Jazz Night

    Reynolds Tavern, 7 Church Cir, Annapolis · verified Oct 9
    See details

    Reynolds Tavern pairs fine dining with live jazz from the Unified Jazz Ensemble, creating an evening that blends great food, vibrant music, and a sense of history. Enjoy a seated dinner, or opt for casual fare in the 1747 Pub while the band performs. There is a $10 cover for the music, which is waived for guests who choose the fine dining experience.

    Event website ↗
  • Wed 8pm

    Gerald Albright

    Rams Head On Stage, 25 West St, Annapolis
    See details

    Rams Head On Stage presents Gerald Albright, a celebrated saxophonist and bassist whose work spans contemporary jazz, R&B, and pop. This show is open to all ages. Raised in Los Angeles, Albright mastered the saxophone early and later added bass to his toolkit after being inspired by Louis Johnson. Shortly after graduating from the University of Redlands, he joined Patrice Rushen’s band and even finished a tour on bass when the original bassist departed. Throughout the 80s he became a sought-after studio and touring player, performing with artists such as Anita Baker, Ray Parker Jr., Atlantic Starr, The Temptations, Maurice White, Les McCann, Teena Marie, the Winans, and Whitney Houston. He launched his solo path with Just Between Us in 1987, helping define the emerging smooth jazz sound and earning radio success, chart placements, and spots on all-star outings like Guitars & Saxes and Groovin’ For Grover. In the late 90s he led a big band while touring with Phil Collins and teamed with Will Downing on the album Pleasures of the Night. His recent discography includes Grammy-nominated releases Pushing the Envelope and Slam Dunk, plus acclaimed collaborations like 24/7 with Norman Brown and the Dave Koz and Friends Summer Horns project featuring Mindi Abair and Richard Elliot. Additional albums include Smooth, Groovology, Kickin’ It Up, and Sax for Stax. Known for commanding both sax and bass, Albright shapes performances that travel through shifting textures, rhythms, harmonies, and moods, inviting listeners into a polished blend of contemporary R&B and urban jazz.

    Event website ↗
  • Fri 7pm

    Elks Halloween Open Mic

    Broadneck Elks Lodge 2608, 931 LAKE DR, Arnold · verified Oct 9
    See details

    This open-invite Halloween open mic takes place at Broadneck Elks Lodge 2608. A full band setup will be available for performers. Food and drinks will be available for cash purchase. A 50/50 raffle is also planned.

    Event website ↗

All upcoming events, day by day

Every event we track in Anne Arundel County this week, in order. After one kind of thing? Live music and family events have their own calendars.

Wednesday, October 14 6 events
  • 6am

    Spirit Day: Severna Park Music Boosters

    511 Governor Ritchie Hwy, Severna Park · verified Oct 11
    See details

    Support Severna Park High Music Boosters by choosing Chick-fil-A Severna Park for breakfast, lunch, or dinner. Dine in, take it to go, or use the drive-thru. At checkout, mention that your order is for the school so it is counted. If ordering through the mobile app, enter the organization code chicken, which is case sensitive, when the Community Cares screen appears, then select Yes to confirm your support. Enjoy your meal while backing the program.

    Event website ↗
  • 5:30pm

    Sparks Solo

    Nonna Angela's Italian Bistro & Wine Bar, 2225 Defense Hwy, Crofton
    See details

    Sparks presents a monthly solo performance at a traditional style Italian bistro and wine bar.

    Event website ↗
  • 6:30pm

    Jazz Night

    Reynolds Tavern, 7 Church Cir, Annapolis · verified Oct 9
    See details

    Reynolds Tavern pairs fine dining with live jazz from the Unified Jazz Ensemble, creating an evening that blends great food, vibrant music, and a sense of history. Enjoy a seated dinner, or opt for casual fare in the 1747 Pub while the band performs. There is a $10 cover for the music, which is waived for guests who choose the fine dining experience.

    Event website ↗
  • 7pm

    Versed Fox Book Club

    Old Fox Books & Coffeehouse, 35 Maryland Ave, Annapolis
    See details

    Versed Fox Book Club devotes its October meeting to the work of John Milton, with a focus on Paradise Lost. The conversation explores rebellion, free will, and the complexities of good and evil, while reflecting on how Milton’s vivid language and sweeping vision have resonated with readers for centuries.

    Event website ↗
  • 7:30pm

    Trivia Night | Dave & Buster's - Hanover MD - WED 730p - @LeaderboardGames

    Dave & Buster's (Hanover, MD), 7000 Arundel Mills Cir, Hanover · verified Oct 11
    Free

    Test your knowledge at a fast-paced trivia night at Dave & Buster's in Hanover, MD. Play a live hosted, competitive game that features a mix of question styles, including an image round and a music round. Use your phone to submit answers, track your standing on the leaderboard, and rack up points. Teams of up to six can collaborate on questions spanning pop culture, sports, history, science, and more. It is free to play, and prizes are awarded to the winners.

    Event website ↗
  • 8pm

    Gerald Albright

    Rams Head On Stage, 25 West St, Annapolis
    See details

    Rams Head On Stage presents Gerald Albright, a celebrated saxophonist and bassist whose work spans contemporary jazz, R&B, and pop. This show is open to all ages. Raised in Los Angeles, Albright mastered the saxophone early and later added bass to his toolkit after being inspired by Louis Johnson. Shortly after graduating from the University of Redlands, he joined Patrice Rushen’s band and even finished a tour on bass when the original bassist departed. Throughout the 80s he became a sought-after studio and touring player, performing with artists such as Anita Baker, Ray Parker Jr., Atlantic Starr, The Temptations, Maurice White, Les McCann, Teena Marie, the Winans, and Whitney Houston. He launched his solo path with Just Between Us in 1987, helping define the emerging smooth jazz sound and earning radio success, chart placements, and spots on all-star outings like Guitars & Saxes and Groovin’ For Grover. In the late 90s he led a big band while touring with Phil Collins and teamed with Will Downing on the album Pleasures of the Night. His recent discography includes Grammy-nominated releases Pushing the Envelope and Slam Dunk, plus acclaimed collaborations like 24/7 with Norman Brown and the Dave Koz and Friends Summer Horns project featuring Mindi Abair and Richard Elliot. Additional albums include Smooth, Groovology, Kickin’ It Up, and Sax for Stax. Known for commanding both sax and bass, Albright shapes performances that travel through shifting textures, rhythms, harmonies, and moods, inviting listeners into a polished blend of contemporary R&B and urban jazz.

    Event website ↗
Thursday, October 15 8 events
  • 10am

    Annapolis Sailboat Show

    Annapolis Boat Show, 110 Compromise St, Annapolis
    See details

    Just Catamarans will be at the Annapolis Sailboat Show with its service and brokerage teams available to assist visitors. Attendees can connect with the team for help and information.

    Event website ↗
  • 11am

    Historic Baldwin Hall Day at Ledo Pizza Millersville

    Ledo Pizza (Millersville, MD), 8531 Veterans Highway, Millersville · verified Oct 11
    See details

    Support Baldwin Hall by dining at Ledo Pizza in Millersville. Purchase a midday or evening meal, then place your receipt in the basket at the restaurant so your purchase helps raise funds for its preservation.

    Event website ↗
  • 4pm

    Afterschool Art Class

    1324 Cape Saint Claire Rd, Annapolis · verified Oct 11
    See details

    Give your child a relaxed afterschool outlet with a creative class in Annapolis, Maryland that blends play, art, and sensory discovery. Kids explore materials, try simple experiments, and bring home something new they made. The experience fosters connection with peers and helps build confidence through hands-on creativity and imagination. Limited openings remain.

    Event website ↗
  • 5pm

    Family Game Night at sweetFrog Laurel

    3341 Corridor Marketplace, Laurel · verified Oct 11
    See details

    At sweetFrog Laurel, families can settle in for a game night featuring board games, dominoes, and cards to play together with the kids. A special deal offers four kids cups for $20, and a family four pack can be reserved. Cups are available at the cashier.

    Event website ↗
  • 5:30pm

    Make a Mondo Bag with Nancy Freeman

    Cottonwoodinthepark, 548 benfield road, Severna Park · verified Oct 11
    See details

    Make a Mondo Bag with Nancy Freeman in a hands-on class that guides you through creating a bag you will be excited to use or gift. Learn her simple method for helping the bag keep its shape so it stands upright, making it easy to reach your belongings. The project lends itself well to thoughtful presents for friends and family.

    Event website ↗
  • 7pm

    Maryland Coffee Talk

    Panera Bread 8125 Ritchie Highway Pasadena, MD 21122, 8125 Governor Ritchie Hwy, Pasadena · verified Oct 11
    See details

    An inviting gathering for TACA families centered on honest conversation, lived experiences, and practical resources. Attendees connect with others who understand the autism journey, share ideas, and leave with encouragement and a supportive community in their corner.

    Event website ↗
  • 8pm

    Comedian Josh Blue of Last Comic Standing w/ Stephen Agyei

    Rams Head On Stage, 25 West St, Annapolis
    See details

    Josh Blue, winner of Last Comic Standing, brings his sharp wit and off-the-cuff humor to Rams Head On Stage in Annapolis with Stephen Agyei. A seasoned headliner, he has appeared on The Tonight Show Starring Jimmy Fallon, performed at the William H. Macy Gala during Just for Laughs in Montreal, and recorded his fifth hour, Broccoli, at Comedy Works in Denver. Following a third-place finish on America’s Got Talent in 2021, he has continued to tour widely, delivering more than 200 shows a year. Known for quick improvisation and an ever-evolving set, no two performances are the same. This event is for ages 18 and over.

    Event website ↗
Friday, October 16 6 events
  • 9am

    Little Leapers at Sky Zone Gambrills

    986 Waugh Chapel Way, Gambrills · verified Oct 11
    See details

    Little Leapers at Sky Zone Gambrills creates a dedicated jumping session for children ages 6 and under to bounce, play, and explore in a space tailored to them. Parents are welcome to participate alongside their kids. Sky Socks are required for all participants. The first adult is included at no additional cost, and a second adult can join for $5. Basic and Elite members receive free entry.

    Event website ↗
  • 5:30pm

    Kids Night

    My Gym Crofton, 1119 State Route 3 N, Gambrills · verified Oct 9
    See details

    Kids get a monthly night of activity featuring themed games, relay challenges, tumbling, obstacle courses, and other fast-paced fitness fun. The evening wraps up with pizza. Parents can plan a date night while the organizers handle the entertainment.

    Event website ↗
  • 7pm

    Elks Halloween Open Mic

    Broadneck Elks Lodge 2608, 931 LAKE DR, Arnold · verified Oct 9
    See details

    This open-invite Halloween open mic takes place at Broadneck Elks Lodge 2608. A full band setup will be available for performers. Food and drinks will be available for cash purchase. A 50/50 raffle is also planned.

    Event website ↗
  • 7pm

    Showroom Shine Haunted Carwash

    Showroom Shine Car Wash (Showroom Shine Car Wash Glen Burnie), 7241 E Furnace Branch Rd., Glen Burnie · verified Oct 11
    See details

    Face a haunted carwash at Showroom Shine Car Wash Glen Burnie, where the tunnel fills with eerie lighting, fog, and startling moments while your vehicle is washed. Enjoy the thrills with family and friends from the safety of your seats. Admission is $25 per vehicle, paid on site at entry. For safety, all passengers must stay inside the car with windows closed the entire time. Arrive early since lines can build quickly, and follow the traffic cones and attendants for smooth queuing. The experience is open to all ages, with light scares and costumed performers appearing throughout the wash.

    Event website ↗
  • 8pm

    Intimate Jazz presents - Sue Matthews/Robert Redd

    49 West Coffeehouse, Winebar & Gallery, 110 Cathedral St, Annapolis · verified Oct 11
    See details

    Sue Matthews and Robert Redd return to 49 West Coffeehouse, Winebar & Gallery with another Songbook Series program presented by Intimate Jazz. The performance features selections from their upcoming album, Perfect Match, along with stories about the performers, composers, and lyricists behind the Great American Songbook.

    Event website ↗
  • 9pm

    Weekly Karaoke Party

    1502 Annapolis Rd, Odenton · verified Oct 11
    See details

    A weekly karaoke party packed with singing, dancing, and standout performances offers a lively night for friends and fellow music fans. Participants can belt out favorite tunes while enjoying $5 off all Margaritas. A friendly contest adds to the fun, with first place earning a $25 gift certificate and second place receiving an appetizer for two. Every participant is also entered into a drawing for a 3-day mini-vacation. Open to seasoned vocalists and first-timers alike, it is a welcoming stage for anyone ready to step up to the mic.

    Event website ↗
Saturday, October 17 21 events
  • 9:30am

    Meet and Ride

    Chesapeake Cycles, 104 Defense HWY, Annapolis
    See details

    Enjoy a relaxed, no stress meet and ride held on the third Saturday of every month. If rain or other weather causes delays, it shifts to Sunday or to the fourth Saturday or Sunday as needed.

    Event website ↗
  • 10am

    Elementary School Allowance Workshop

    CovingtonAlsina, 67 West St, Annapolis
    See details

    Designed for elementary students ages 9 to 11, this interactive session helps kids learn how to earn, handle, and think about money with confidence. Children practice the four basic choices for every dollar: saving, spending, giving, and investing, while exploring simple ways to make money and how financial decisions connect to happiness. Part of a broader kids’ financial education series that covers topics from allowances to financial literacy and preparation for college, this workshop focuses on building responsible habits from an early age.

    Event website ↗
  • 10am

    Fall Saturdays at Ridge Grow

    Ridge Grow, 244 Old Mill Bottom Rd S, Annapolis · verified Oct 9
    See details

    Ridge Grow hosts a Saturday celebration of autumn throughout the garden center. Pick out pumpkins and colorful mums, choose corn stalks and straw bales for seasonal decorating, and browse ornamental cabbages, kale, annuals, and other in-season vegetables. Enjoy family activities and take seasonal photos among the displays. A changing selection of food trucks is featured from week to week, and the activities also vary each Saturday. There is no admission charge.

    Event website ↗
  • 11am

    Visiting Author - Erin P.T. Canning

    Maryland Renaissance Festival, 1821 Crownsville Rd, Annapolis · verified Oct 9
    See details

    Visiting author Erin P.T. Canning invites readers of epic romantasy to a meet and greet with a book signing. Attendees can meet the author and have books signed.

    Event website ↗
  • 11am

    A.M. Robin

    Page After Page, 1797 Crownsville Rd, Annapolis
    See details

    Connect with the author during a casual meet and greet and have books signed. Learn more about Anna and her books online.

    Event website ↗
  • 11am

    Visiting Author - Jaz Azari, Young Adult Fantasy Fiction

    Maryland Renaissance Festival, 1797 Crownsville Rd, Annapolis
    See details

    Meet the author and take part in a book signing. Learn more about Jaz's books online.

    Event website ↗
  • 11am

    FREE Family Event: Harvest Fest

    600 N Bestgate Rd, Annapolis · verified Oct 11
    Free

    A family friendly afternoon features complimentary food, fair style games, a petting zoo, axe throwing, face painting, and other activities. A cake walk adds to the fun with a chance to win a homemade dessert to take home.

    Event website ↗
  • 11am

    SAT 10/17/26: Luther Strode Anniversary signing with Justin Jordan, Tradd Moore, Felipe Sobreiro

    7992 Crain Hwy S, Glen Burnie · verified Oct 11
    See details

    Celebrate the Luther Strode #1 Anniversary Edition at Third Eye Glen Burnie with a creator signing featuring Justin Jordan, Tradd Moore, and Felipe Sobreiro. Meet the team behind the series and get your copies signed in person. The first 10 people in line receive a free gift limited to this event. Signed pre-orders and VIP options are available through the organizer’s site.

    Event website ↗
  • 11am

    The Wine Festival at Kurtz's Beach 2026

    Kurtz's Beach, 2066 Kurtz Ave, Pasadena · verified Oct 11
    See details

    Marking its 11th year, the wine festival at Kurtz’s Beach celebrates a continuing tradition. This milestone edition recognizes more than a decade dedicated to wine at this festival.

    Event website ↗
  • 12pm

    Howl-o-Ween Adoption Event at Petco Severna Park

    Petco (571 Ritchie Hwy, Severna Park, MD), 545 Governor Ritchie Hwy, Severna Park · verified Oct 11
    Free

    Celebrate the season at a Howl-o-Ween adoption event hosted at Petco Severna Park. The BFF Waggin' will attend with adoptable dogs and cats looking for loving homes. Fees for adoptions completed at the event are waived, and standard adoption procedures still apply. Expect a cheerful Halloween atmosphere and plenty of chances to meet a new companion.

    Event website ↗
  • 12pm

    Salsa Lessons for Absolute Beginners! Fall Series! Saturdays @12pm!!

    Glen Burnie · verified Oct 11
    See details

    Kick off a welcoming fall series for brand-new salsa dancers in Glen Burnie, MD. BSDC instructor Emily Imber leads Salsa 101 with clear, step-by-step guidance in footwork, timing, and partner skills, introducing fresh moves and combinations each session so progress builds steadily. Expect lively music, supportive coaching, and a structure that helps create a strong foundation by the end. Come solo or with a companion, since partners are rotated to give everyone a chance to practice. Single class attendance is only permitted during the first two weeks of the session, and monthly enrollment is required to continue through the series. Pricing options include $30 for a single class when prepaid online, $35 at the door, or a $110 four-class pass. Pre-registration is required for all classes. Refunds are not offered unless an event is canceled or moved, and transfers to other classes and events are available.

    Event website ↗
  • 1pm

    Financial Literacy for Middle School

    CovingtonAlsina, 67 West St, Annapolis
    See details

    Middle schoolers ages 12 to 14 can build essential money skills in this workshop. As part of the Kids' Financial Education Programs, it covers the basics of managing money, introduces useful tools for day-to-day financial decisions, and outlines early steps toward long-term financial success. The session is designed to support informed choices as students move into their next stage of life. The broader program also offers age-appropriate workshops for elementary, middle, and high school students, touching on topics from allowances and core financial literacy to getting ready for college. These engaging and educational sessions help establish smart money habits from an early age.

    Event website ↗
  • 4pm

    Mascot Visit at sweetFrog Laurel

    3341 Corridor Marketplace, Laurel · verified Oct 11
    Free

    At sweetFrog Laurel, guests can meet one of the sweetFrog mascots, Scoop or Cookie, during a special appearance. There will be opportunities for photos and lighthearted fun, making it easy to bring home a memory with these characters. Free tickets are available to confirm attendance.

    Event website ↗
  • 5pm

    6th Annual Hope Dance Concert

    Annapolis Town Center, 1910 Towne Centre Blvd, Annapolis · verified Oct 9
    See details

    Greater Annapolis Ballet presents the 6th Annual HOPE Dance Concert, an uplifting evening that blends dance, community, and purpose. Performers unite to showcase the expressive power of dance while supporting a cause that matters to the local community. The event highlights creativity, unity, and hope, and is dedicated to making a positive impact.

    Event website ↗
  • 5pm

    Annapolis RISE Flag Football 2026 Fall Season

    Annapolis High School, 2700 Riva Rd, Annapolis · verified Oct 11
    See details

    Registration is open for the Fall 2026 RISE Flag Football season in Annapolis. Games use a six on six format on the Annapolis High School turf fields. The league welcomes boys and girls in kindergarten through eighth grade, along with a girls high school division for grades 9 through 12. Teams play six to eight games, playoffs included. The program has served Annapolis families since 2015 across 22 seasons. A $30 savings on registration is noted.

    Event website ↗
  • 6pm

    Hyland Brothers

    Graduate Annapolis, 126 West St, Annapolis · verified Oct 9
    See details

    Experience a live music performance with musicians playing in real time. Enjoy a set of songs delivered in person, creating a shared moment between performers and audience. A simple way to take in instruments and melodies performed live.

    Event website ↗
  • 6pm

    Party in the Port 2026

    Eastport Yacht Club, 317 1st St, Annapolis · verified Oct 9
    See details

    Open to all, this waterfront celebration picks up the energy after the Boat Show at Eastport Yacht Club, blending live music with harbor views and a relaxed, high-spirited vibe. Slip Hippies gets things started with an Annapolis acoustic set that weaves together classic rock, 80s favorites, country, beach and island tunes, soul, Motown, and contemporary hits. ONO, also known as One Night Only, follows with powerful vocals, tight rhythms, and a set built to keep the dance floor moving. Cool fall evenings pair perfectly with Chili in the ’Port, a build-your-own chili bar stocked with plenty of toppings, along with the club’s signature libations. Ticket options include advance purchase at $20 plus processing, an online-only two-ticket bundle for $35 plus fees, and a $25 gate price. Children 5 and under are admitted free. Entry is through the main gate only, with no access from the marina docks. The event is rain or shine and tickets are nonrefundable. Pets are not permitted. Sustainability is front and center, with 100 percent compostable service, no single use plastic, and green volunteers staffing eco stations to keep the party waste free. Guests can also see the club’s Clean Marina and Green Building features, including a permeable parking surface, rain barrels, and landscaping that helps reduce runoff.

    Event website ↗
  • 6pm

    Boney James

    Rams Head on Stage, 25 West St, Annapolis · verified Oct 9
    See details

    At Rams Head On Stage, saxophonist and composer Boney James delivers a concert shaped by the deliberate, growing intensity behind his album Slow Burn, which he produced with collaborators including Marcus Miller, Cory Henry, Jairus Mozee, October London and Rick Braun. The program draws from tracks such as Arcadia with Miller on acoustic bass, an interpretation of Butterfly by Herbie Hancock and Bennie Maupin featuring Miller and Henry, the single All I Want Is You with October London, the groove-forward Slide with his touring band, A Little Romance, the upbeat Gonna Have a Good Time and The Bounce, Between the Lines and a take on Stanley Turrentine’s Sugar with Braun on trumpet. James’s career includes multiple GRAMMY and NAACP Image Award nominations, a Soul Train Award, several RIAA Gold records and 20 number one singles on the Billboard Smooth Jazz chart. This event is open to all ages.

    Event website ↗
  • 8pm

    Weekly Music Bingo Event

    1502 Annapolis Rd, Odenton · verified Oct 11
    Free

    This weekly music bingo night at The All American Steakhouse in Odenton invites players to put their music knowledge to the test for a chance to win prizes. There is no cost to participate. Guests can enjoy $5 rail drinks, $6 Long Island Iced Teas, half-price domestic drafts, and 50 percent off cheesesteaks and fries while the games are underway.

    Event website ↗
  • 9pm

    Boney James

    Rams Head On Stage, 25 West St, Annapolis · verified Oct 9
    See details

    Saxophonist and composer Boney James brings his contemporary jazz sound to the stage for an all ages performance. His latest chapter centers on Slow Burn, a self-produced Concord Records release that captures music building with thoughtful intensity. The project features notable collaborators, including Marcus Miller contributing rare acoustic bass on Arcadia and returning for a fresh take on Herbie Hancock and Bennie Maupin’s Butterfly alongside Cory Henry on electric piano. Vocalist October London appears on the single All I Want Is You. Slide puts James on tenor sax and keyboards with his touring band, while A Little Romance, Gonna Have a Good Time, The Bounce, and Between the Lines keep the groove alive. The collection also offers a spirited version of Stanley Turrentine’s Sugar with longtime collaborator Rick Braun on trumpet. James arrives with a track record that includes four GRAMMY nominations, three NAACP Image Award nominations, a Soul Train Award for Best Jazz Album, four RIAA Gold certifications, recognition by Billboard among the top contemporary jazz artists of the decade, and a milestone of 20 number one singles on the Billboard Smooth Jazz chart. From an early switch from clarinet to saxophone to professional tours with artists such as The Isley Brothers and Teena Marie, he has continued to craft melodies and grooves that connect with listeners.

    Event website ↗
  • 9:45pm

    Stan & Joe's Saloon

    Stan and Joe's Saloon, 37 West St, Annapolis
    See details

    Leftovers night brings a party to Stan & Joe's in Annapolis.

    Event website ↗
Sunday, October 18 6 events
  • 10am

    Earleigh Heights VFC Holiday Craft Fair

    161 Governor Ritchie Hwy, Severna Park · verified Oct 11
    See details

    Kick off your holiday shopping at the Earleigh Heights Volunteer Fire Company Holiday Craft Fair. Explore a variety of goods from local vendors, including Skeids, which offers more than 40 seasoning blends you can smell before buying. The event supports the Earleigh Heights Volunteer Fire Company and provides a friendly setting to discover unique gifts.

    Event website ↗
  • 10am

    Modern Mama Tees & Co. at Earleigh Heights Fire Department

    Earleigh Heights Volunteer Fire Company, 161 Ritchie Hwy, Severna Park · verified Oct 11
    See details

    Modern Mama Tees & Co. will be on site at Earleigh Heights Fire Department with a fresh selection of boutique apparel and graphic T shirts. Browse and buy in person, or keep shopping anytime using the app. Please note they are participating as a vendor and are not accepting applications or handling sign ups.

    Event website ↗
  • 11am

    Visiting Author - Fiona Fenn, Queer Adult Romantasy

    Maryland Renaissance Festival, 1821 Crownsville Rd, Annapolis
    See details

    Visiting author Fiona Fenn hosts a meet and greet and book signing focused on queer adult romantasy. Learn more about her books and get a signature.

    Event website ↗
  • 11am

    Visiting Author - Shelley Puhak, Historical True Crime

    Maryland Renaissance Festival, 1821 Crownsville Rd, Annapolis · verified Oct 11
    See details

    A visiting author appearance with Shelley Puhak offers a friendly meet and greet paired with a book signing, highlighting her work in historical true crime. Attendees can meet the author and have books signed.

    Event website ↗
  • 11am

    Annual Harvest Festival

    North Glen Community Church, 508 W Furnace Branch Rd, Glen Burnie · verified Oct 11
    Free

    Guests can celebrate the season at a free outdoor neighborhood harvest gathering that centers on community and connection. The day features family-friendly games, hands-on craft stations, an inflatable bounce house, and live music in the open air. A quiet prayer area will be available for reflection or support. Children age ten and under can receive a complimentary pumpkin while supplies last, and warm food and snacks will be provided. Early arrival is encouraged for the pumpkin giveaway due to limited quantities. It offers a relaxed autumn outing with activities for all ages.

    Event website ↗
  • 8pm

    Five For Fighting

    Rams Head on Stage, 25 West St, Annapolis · verified Oct 9
    See details

    Five For Fighting appears with a string quartet for a night centered on John Ondrasik's piano and falsetto vocals. The platinum selling, Grammy nominated artist is known for hits like "Superman (It's Not Easy)" and "100 Years", along with "The Riddle", "Chances", "World", and "Easy Tonight". Across six studio albums his songs have reached wide audiences and been featured in films and television including The Blind Side, Hawaii Five-O, The Sopranos, and Code Black. His work also includes recent pieces such as "Blood on My Hands", "Can One Man Save The World?" and "OK". Also appearing is Lace & Lee, a folk rock duo whose ethereal harmonies draw on 60s and 70s storytelling with a touch of Celtic spirit. This event is open to all ages.

    Event website ↗
Monday, October 19 6 events
  • 11am

    Very Superstitious!

    William Paca House and Garden, 186 Prince George St, Annapolis · verified Oct 11
    See details

    Explore the William Paca House and Garden on a guided tour focused on the beliefs, folk traditions, and superstitions that shaped daily life in earlier centuries. Trace the origins of familiar customs, from household rituals to lucky tokens and protective practices, and see how some continue today. Along the way, learn how these ideas offered comfort in uncertain times and why their echoes still linger. The experience ends with seasonal refreshments and an opportunity to share a favorite superstition. The route may change because of weather or private functions, so dress for the conditions. Advance registration is encouraged since space is limited.

    Event website ↗
  • 6pm

    Monday Night Mysteries: Expiration Date (10/19)

    Perry's Restaurant, 1210 Annapolis Rd, Odenton · verified Oct 11
    See details

    Part of Monday Night Mysteries at Perry's Restaurant, this interactive, comedic murder mystery centers on aging psychic Perry Normal, founder of Paranormal Understanding, Knowledge and Enlightenment (P.U.K.E.) and host of The Perry Normal Hour. Known for lavish gatherings and years of headline-making predictions, she once forecast a fatal blow to herself exactly one year prior. The suspense builds as the evening unfolds and the question remains... will she make it through the night, all with a playful, spooky tone that suits the Halloween season. The price of $74.50 includes a set menu with multiple options, chef’s choice of dessert, the immersive show, non-alcoholic beverages, tax, gratuity, and free on-site parking. Alcoholic beverages are available for an additional charge. Dietary restrictions can be accommodated with 72 hours notice. There are no extra fees, $74.50 is the final price.

    Event website ↗
  • 7pm

    Charm City Trivia at The Crab Shack!

    The Crab Shack - Crofton, 1260 Crain Highway, Crofton · verified Oct 11
    See details

    Charm City Trivia brings a lively quiz night to The Crab Shack - Crofton in Crofton, MD, featuring a visual component. Happy Hour is available beforehand. Winners of toss-up questions receive bartender’s choice shots, and the top two teams each week earn gift cards.

    Event website ↗
  • 7pm

    Charm City Trivia at CrabTowne USA!

    Crabtowne USA Inc., 1500 Crain Hwy S, Glen Burnie · verified Oct 11
    See details

    It is Burger Monday with $10 burgers, first come, first served. Prizes are awarded for toss ups, and the top two teams receive prizes every week.

    Event website ↗
  • 7:30pm

    Pete Best and Dana Cooper - Live 49 West

    49 West Coffeehouse, Winebar, & Gallery, 49 West St, Annapolis · verified Oct 11
    See details

    ITZALL Goode and SHC Music Tribe team up to bring Pete Best and Dana Cooper to 49 West Coffeehouse, Winebar, & Gallery for a live performance. Pete Best, a Maryland singer songwriter, blends southern rock grit with country storytelling rooted in everyday life, from family and resilience to turn-it-up bar tunes. He built an early following around Baltimore and Washington before relocating to Nashville, and with his band Peterbuilt has opened for Jack Ingram and Pat Green. His debut album, Built to Last, arrived in 2008, the same year he connected with fans at the CMA festival. Raised in Annapolis, he gravitated to country for its lyric focus and later wrote for Dan Hodges Music from 2011 to 2016. Dana Cooper brings a catalog of more than 30 albums and continues to tour widely. His latest release, The Ghost of Tucumcari, features guest appearances by Lyle Lovett, Hayes Carll, Susan Gibson, Darden Smith, and Shake Russell, and was voted No. 1 in the 2024 Americana Highways poll. His performances span folk, rock, country, and Americana, showcasing flat picking, finger picking, percussive strumming, and harmonica alongside engaging storytelling. Tickets are available online for $20, or $23.18 with fees, and the door price is $25. If you prefer not to purchase in advance, seats can be reserved by calling 410-626-9796 and the door rate will apply at entry. An online purchase serves as the reservation, so there is no need to call the venue in that case.

    Event website ↗
  • 8pm

    Evan Honer

    Rams Head on Stage, 33 West St, Annapolis · verified Oct 9
    See details

    Evan Honer brings It’s An Even Longer Road Tour to Rams Head On Stage in Annapolis with special guest Zach Seabaugh. This event is open to all ages. Honer’s recent years have been full of momentum, from a move to Nashville and an international tour schedule to building a recording space in his garage and running Cloverdale Records out of his living room, a label featuring 25 artists and more than 100 releases. In 2024 he played nearly 100 shows in support of his second album, Fighting For, while writing the next chapter of his catalog. His rise accelerated when his take on Tyler Childers’ Jersey Giant drew more than 200 million streams, a breakthrough that arrived while he was still finishing college, playing solo gigs at night, and training with a Division 1 swim team. He released his debut, West On I-10, on graduation day and quickly turned into a relentless touring artist. Everything I Wanted, recorded in 18 days at his home studio, brings his indie and alternative pop influences to the front without leaving behind his Americana roots. The album features strings from neighbor Kate Stephenson, horn accents, pedal steel, and contributions from close collaborators. Across it all are intimate songs, vivid storytelling, and an expressive vocal style shaped by an artist learning to appreciate the moment. Career highlights include more than 500 million streams, an RIAA gold certification for Jersey Giant, sold out dates with Wyatt Flores, and continued growth for Cloverdale Records.

    Event website ↗
Tuesday, October 20 6 events
  • 10am

    Tots

    Town Center, 307 Sail Pl, Annapolis
    See details

    Annapolis Town Center hosts a monthly program designed for families with preschool-age children, featuring a new theme each time and activities led by local business partners, with support from sponsor Crab Kickers. This edition focuses on Farmyard Fun with a petting zoo. Families can stay for lunch and take advantage of special offers at participating eateries when an adult purchase is made. At Augie’s Mussel House, a child’s entree is complimentary with an adult main course. Neo Pizza provides a free kids meal with a side and beverage for guests 12 and under when an adult meal is purchased. PF Chang’s offers a free kids meal with an adult lunch purchase. Toastique gives a free house made treat with the purchase of a large smoothie or an item of similar price. True Food Kitchen includes a complimentary kids meal with dine-in purchases of $25 or more, with the $25 minimum excluding the kids meal. Giolitti Delicatessen serves a free kids size Italian mac and cheese for dine-in, with no substitutions.

    Event website ↗
  • 6pm

    Art Bar

    Forward Brewing, 421 4th St, Annapolis · verified Oct 11
    See details

    ArtFarm Studios transforms Forward Brewing into a relaxed art bar where creativity and community come together. The evening begins with time to enjoy dinner and a drink, followed by a warm welcome from the hosts who introduce four hands-on projects to choose from, with options that can include watercolor, collage, art journals, magnets, or friendship bracelets. Settle in to make something with your hands alongside friendly company, then head home with a finished piece you created. It suits a night out with friends, a creative date, or a solo outing that makes it easy to meet new people through shared making.

    Event website ↗
  • 7pm

    Women, Wine, & Wisdom™ Annapolis

    Rams Head Tavern, 33 West St, Annapolis
    See details

    Women, Wine & Wisdom in Annapolis creates a welcoming place for women to talk about finances in a low-pressure way, connect with others, and enjoy a glass of wine while learning from professionals. This edition centers on estate planning, featuring an attorney who will cover essentials like wills, trusts, and estates to help participants start considering their own plans. The evening begins with time to connect, then continues with a presentation and a roundtable conversation where attendees can ask questions and receive straightforward, practical guidance from guest professionals. Each gathering offers a new topic while maintaining the same supportive community. The event takes place at Rams Head Tavern Annapolis.

    Event website ↗
  • 7pm

    Charm City Trivia

    GameOn Bar & Arcade, 114 West St, Annapolis · verified Oct 12
    See details

    A trivia night featuring a friendly crowd, food, and lots of laughter.

    Event website ↗
  • 7:30pm

    PFLAG Annapolis/AACo Support Meeting

    Unitarian Universalist Church of Annapolis, 333 Dubois Rd, Annapolis · verified Oct 9
    See details

    PFLAG Annapolis/AACo hosts a support meeting with three concurrent groups designed for youth, adults, and parents or allies. The gathering takes place at the Unitarian Universalist Church Annapolis, not in the FAHS House behind the church. Adults meet on the lower level, with direct entry from the parking lot through the green double doors. Youth and parents or allies meet on the main floor and should use the main entrance.

    Event website ↗
  • 8pm

    Acoustic Alchemy

    Rams Head on Stage, 25 West St, Annapolis · verified Oct 9
    See details

    Acoustic Alchemy appears at Rams Head On Stage for an all-ages performance. With more than three decades of recording and touring, the group continues to share music only when it feels fully ready, embracing a range of influences rather than fitting into a single style. Their latest EP, The Empire of Lights, collects four tracks that range from the twangy shuffle of 8,000 Miles to the reggae-leaning Alisio, the upbeat lift of Back to Back, and the relaxed sway of Other People. It is the first in a planned series of shorter releases that will eventually form a full album, designed to play beautifully from start to finish as well as one song at a time. The EP is available on music platforms worldwide, and a limited run of CDs will be offered at live shows.

    Event website ↗

All upcoming events160 more events through Dec 31

Everything else on Anne Arundel County's calendar over the next 30 days, in order.

Wednesday, October 21 7 events
  • 3pm

    Opening Day

    Warfield Sisters Farm, 8221 Meadowood Dr, Hanover · verified Oct 11
    See details

    Something new begins on the farm with Opening Day. It embraces a shop local focus and mentions Hanover, Fort Meade, and Severn along with Warfield Sisters Market.

    Event website ↗
  • 5:30pm

    McCoy Solo

    Nonna Angela's Italian Bistro & Wine Bar, 2225 Defense Hwy, Crofton · verified Oct 11
    See details

    Enjoy an evening of food and music with Steve.

    Event website ↗
  • 6pm

    Halloween Signs Paint Party at Pherm Brewing w Maryland Craft Parties

    Pherm Brewing Company, Gambrills · verified Oct 11
    See details

    Create festive wooden cutout signs at a hands-on paint party hosted at Pherm Brewing Company in Gambrills, MD. Participants can choose from pre-drawn options like Hocus Pocus Pumpkin, Oriole Bird Witch Hat, Raven Bird Witch Hat, Natty Boh Witch Hat, and Jack-O-Lantern Witch Hat, or start with blank shapes such as a Pumpkin, Boo signs, or a Pumpkin Witch Hat to design from scratch. No experience is needed. All supplies and aprons are provided, and instructors offer step-by-step guidance. Every piece can be customized with your colors, details, and layout. A food truck will be on site, and attendees are welcome to bring their own food or order in. There is no need to print tickets, just give your name upon arrival. Seating is limited, tickets are not sold at the door, and all sales are final and non-refundable. Groups purchasing separately can request to sit together by emailing marylandcraftparties@yahoo.com in advance. If attending in person is not possible, take-home kits are available by call or text at 443-995-7193 or by email.

    Event website ↗
  • 6:30pm

    Jazz Night

    Reynolds Tavern, 7 Church Cir, Annapolis · verified Oct 11
    See details

    Settle into Reynolds Tavern for an evening of live jazz featuring the Unified Jazz Ensemble. Choose a fine dining experience in the main restaurant or stop by the 1747 Pub for casual bites while the music plays. There is a $10 cover, which is waived for guests enjoying the fine dining menu. It is a welcoming spot in Annapolis where great food, timeless tunes, and local history come together.

    Event website ↗
  • 7pm

    Old Fox Bibliophiles Book Club

    35 Maryland Ave, Annapolis
    See details

    Old Fox Bibliophiles hosts a discussion of The Saturday Night Ghost Club by Craig Davidson. Set in Niagara Falls during the 1980s, the novel follows twelve-year-old Jake through a summer of spooky stories, unusual discoveries, and surprising secrets, offering a nostalgic coming of age backdrop for conversation.

    Event website ↗
  • 7:30pm

    Trivia Night

    Dave & Buster's, 7000 Arundel Mills Cir, Hanover · verified Oct 12
    Free

    Enjoy a free, live-hosted trivia game at Dave & Buster's in Hanover. Teams of up to six use their phones to submit answers and earn points across categories that include pop culture, sports, history, and science. The game features image and music rounds, a real-time leaderboard to track standings, and prizes for the winners. Suitable for dedicated trivia fans and casual groups alike.

    Event website ↗
  • 8pm

    James Austin Johnson

    Rams Head On Stage, 25 West St, Annapolis
    See details

    At Rams Head On Stage, comedian and actor James Austin Johnson from Saturday Night Live takes the spotlight. Now in his fourth season on the show, he is widely known for his precise portrayal of Donald Trump. His work spans television and film, with appearances in Barry, Better Call Saul, She Said, and Hail, Caesar!, and he voices the Grinch in Wondery’s ’Tis the Grinch Holiday Podcast, which recently concluded its second season. In 2024 he contributed to two Oscar-nominated films, voicing Pouchy in Inside Out 2 and making a cameo in the Bob Dylan biopic A Complete Unknown starring Timothée Chalamet. This event is for ages 18 and over.

    Event website ↗
Thursday, October 22 2 events
  • 6am

    Spirit Day: Severna Park Stingrays

    511 Governor Ritchie Hwy, Severna Park · verified Oct 11
    See details

    Take part in a Spirit Day supporting the Severna Park Stingrays by enjoying breakfast, lunch, or dinner at Chick-fil-A Severna Park. You can eat in, take it to go, or use the drive-thru. To make sure your purchase is included, tell the cashier you are supporting your school, or, if placing a mobile order, enter chicken as the organization code, case sensitive, on the Community Cares screen and confirm support when prompted. Then sit back and enjoy your meal.

    Event website ↗
  • 8pm

    Gregg Karukas

    Rams Head On Stage, 25 West St, Annapolis
    See details

    This event features Gregg Karukas and is open to guests of all ages. It offers a welcoming setting for everyone to attend together.

    Event website ↗
Friday, October 23 12 events
  • 2pm

    Milk & Cookies Hour- Parent Support Group

    The Rumina Center, 836 Ritchie Hwy, Severna Park · verified Oct 11
    Free

    A free, community parent support hour hosted by The Rumina Center offers a relaxed, judgment-free space to connect with other caregivers of infants. Walk-ins are welcome, and free registration is preferred to help estimate attendance. Guided by LeeAnn Fincham, IBCLC, conversations explore everyday challenges and wins, including feeding, diapering, sleep, building support networks, self-care, and the full range of feelings that accompany early parenthood. Scales will be available for anyone interested in doing a weighted feed. This in-person group is designed to foster connection and reassurance so caregivers can share stories, exchange practical tips, and know they are not alone.

    Event website ↗
  • 5pm

    Parents Night Out!

    1701 Midway Rd, Odenton · verified Oct 11
    See details

    Xtreme Mpact Martial Arts hosts an evening designed to give parents a break while kids enjoy supervised fun. Children can settle in for a movie, snack on popcorn and pizza, and take part in games and other engaging activities in a welcoming setting. The cost is $25 per child. Registration is available through the MyStudio App or by scanning the QR code featured on the event flyer.

    Event website ↗
  • 5:30pm

    Friday Night Kids Club

    ArtFarm Studios, 111 Chinquapin Round Road (suite 200), Annapolis · verified Oct 11
    See details

    The Not Slumber Party offers an easy, kid-free evening for parents while children enjoy a night of activities and relaxation. Tailored for ages 6 to 10, the group is capped at 12 participants. Children are treated to pizza, juice boxes, and snacks, with a game table for interactive fun and an art station for creative expression. The evening wraps up with a cozy movie wind-down. Bring a water bottle, and feel free to send favorite games. A yoga mat, blanket, or sleeping bag can make movie time extra comfortable, and pajamas are welcome for a smooth drop-off.

    Event website ↗
  • 6pm

    Halloween Festival Fundraiser

    Southgate Elementary School, 290 Shetlands Ln, Glen Burnie · verified Oct 11
    See details

    Enjoy a Halloween-themed festival fundraiser that happens alongside a free Trunk or Treat and a book fair. This is a ticketed event, with admission covering hands-on crafts, carnival games, music, and plenty of Halloween fun. Volunteer opportunities are available and include free family admission.

    Event website ↗
  • 6pm

    Harvest Party & Trunk or Treat

    Victory Christian Fellowship Church Inc., 1000 Stewart Ave, Glen Burnie · verified Oct 11
    See details

    Celebrate the season at an annual Harvest Party and Trunk or Treat, a cheerful tradition that brings people together.

    Event website ↗
  • 6:30pm

    Phil Vassar

    Rams Head On Stage, 25 West St, Annapolis
    See details

    Phil Vassar brings his piano-centered country show to Rams Head On Stage, and this performance welcomes all ages. Raised in Lynchburg, Virginia, he soaked up gospel, bluegrass, Motown, and rock influences like Queen and Billy Joel, a blend that shapes his catchy melodies and heartfelt storytelling. Before stepping into the spotlight, he wrote chart-toppers for Alan Jackson, Tim McGraw, Jo Dee Messina, and others, picking up ASCAP’s Country Songwriter of the Year and launching a recording career with Arista. Across a prolific run, he has released nine albums, earned ACM’s Top New Male Vocalist, and notched 10 number one hits and 27 Top 40 singles, with fan favorites including Carlene, Six-Pack Summer, and Just Another Day in Paradise. Now on his 25 Years of Paradise Tour, he delivers an upbeat, piano-forward set filled with singalong moments, drawing on a career that spans performances for U.S. presidents and collaborations with icons such as Merle Haggard and Willie Nelson. With a renewed outlook and a commitment to mentoring young songwriters, he continues to share resilient, authentic stories that resonate with longtime listeners and new fans alike.

    Event website ↗
  • 7pm

    Bountiful Harvest - Costumes & Cocktails

    The Atreeum at Soaring Timbers, 610 North Bestgate Road, Annapolis
    See details

    Bountiful Harvest offers a costumes and cocktails themed celebration billed as the largest fundraiser of the year. Guests can look forward to an open bar, gourmet fare, and both silent and live auctions, along with live music from the Noelle and Jeff Band. Festive costumes are encouraged, and polished cocktail attire is equally welcome. All proceeds support The Annapolis Light House, a homeless prevention support center serving the community. Tickets and sponsorship opportunities are available.

    Event website ↗
  • 7pm

    Five Nights at Freddy's Skate!

    Skate Zone , 1200 Odenton Rd, Odenton · verified Oct 14
    See details

    Skate Zone Odenton presents a Five Nights at Freddy’s themed skating session with a creepy, late-shift vibe. Attendees can enter a scary costume contest, play games, and enjoy spooky fun throughout the rink. Admission is $11 and skate rental is $5. Expect a playful fright factor as the theme channels survival energy on the skating floor.

    Event website ↗
  • 9pm

    One Step Down

    Rams Head Tavern Annapolis, 33 West St, Annapolis · verified Oct 11
    See details

    In the Downbar at Rams Head Tavern Annapolis, One Step Down presents a live acoustic set. Karen Leaf sings and Joe Puleo plays guitar, covering songs across decades and genres, from Nancy Sinatra to Iron Maiden. The night pairs live music with food and drinks.

    Event website ↗
  • 9pm

    Weekly Karaoke Party

    The All American Steakhouse, 1502 Annapolis Rd, Odenton · verified Oct 11
    See details

    This weekly karaoke party brings a lively mix of singing, dancing, and standout performances. It offers a welcoming setting for seasoned performers and first-timers alike, perfect for showcasing vocal talent or simply having fun with friends and fellow music lovers. Enjoy $5 off all Margaritas while belting out favorite tunes and taking part in a friendly contest with prizes. First place receives a $25 gift certificate, second place earns an appetizer for two, and every participant is entered into a drawing for a three day mini vacation. Pick a song, step up to the mic, and enjoy a night of music, good vibes, and a chance to win.

    Event website ↗
  • 9:30pm

    Phil Vassar

    Rams Head On Stage, 25 West St, Annapolis
    See details

    Phil Vassar takes the stage with his signature piano-forward energy, celebrating the 25th anniversary of "Just Another Day in Paradise" as part of his 25 Years of Paradise Tour. The show is open to all ages. Raised in Lynchburg, Virginia, he absorbed gospel, bluegrass, Motown, and rock before finding his voice at the piano, a blend that fuels heartfelt storytelling and catchy hooks. Before launching his own records with Arista, he wrote hits for Alan Jackson, Tim McGraw, Jo Dee Messina, and others, earning ASCAP Country Songwriter of the Year. Across more than 25 years he has released nine albums, received ACM's Top New Male Vocalist, and tallied 10 No. 1 hits and 27 Top 40 singles, with fan favorites like "Carlene," "Six-Pack Summer," and "Just Another Day in Paradise." Known for lively, crowd-connecting performances, he has toured worldwide, performed for U.S. presidents, and shared stages with Merle Haggard and Willie Nelson. After a health scare in 2023, he returns with gratitude and a renewed focus on mentoring young songwriters and giving back, while also preparing new music for 2025.

    Event website ↗
  • 9:30pm

    North Texas Mean Green Football

    Navy-Marine Corps Memorial Stadium, Annapolis · verified Oct 11
    See details

    North Texas faces the Navy Midshipmen in a football matchup at Navy-Marine Corps Memorial Stadium. The meeting features contrasting styles and traditions, with conference implications in play. The Annapolis setting adds to the atmosphere.

    Event website ↗
Saturday, October 24 12 events
  • 4am

    Craft Fair Fall Festival

    Emmanuel Lutheran Church, 8615 Fort Smallwood Rd, Pasadena · verified Oct 12
    See details

    Help spread the word to family and friends about this event. Vendor applications are open and can be submitted by sending a direct message to the organizer or by emailing apexvendor48@gmail.com. For everyone’s safety, only this contact is authorized to accept vendor submissions, so treat any other requests as scams and report them. Thank you for your support.

    Event website ↗
  • 10am

    Memory Pillow-Making Workshop

    John and Cathy Belcher Campus, 90 Governor Ritchie Hwy, Pasadena · verified Oct 12
    See details

    Using a button-down shirt or T-shirt that belonged to a loved one, participants will receive step-by-step guidance to transform it into a keepsake pillow. No sewing experience is required. Attendance is limited to 10 people, registration is required, and the cost is $10. The workshop takes place on the John & Cathy Belcher Campus.

    Event website ↗
  • 11am

    Visiting Author - Doc Coleman, Steampunk Comedy Adventures

    Maryland Renaissance Festival, 1797 Crownsville Rd, Annapolis · verified Oct 11
    See details

    Meet visiting author Doc Coleman for a friendly meet and greet and book signing highlighting his steampunk comedy adventures. Admission requires an MDRF ticket. Details about his books are available on his official website.

    Event website ↗
  • 11am

    Fall Days

    Benson-Hammond House, 7101 Aviation Blvd, Baltimore · verified Oct 11
    See details

    The day features cider, tours of the historic home, and time in the barn foundation area to identify a variety of plants that provide safe cover for the property's furry residents. Live music from The Overtones adds to the fall atmosphere of colorful leaves and cool air.

    Event website ↗
  • 11am

    Children’s Halloween Party

    American Legion Post 40, 500 5th Ave SE, Glen Burnie · verified Oct 11
    See details

    At the Outback picnic area, there will be kid-friendly games and food, along with a trunk-or-treat. Attendees are encouraged to bring pajamas for a collection benefiting Casey Cares.

    Event website ↗
  • 11am

    EL & Company Pop Up

    EL&Company, 4530 Mountain Road, Pasadena · verified Oct 11
    See details

    Modern Mama Tees & Co. sets up at EL & Company for a pop-up featuring new boutique looks and printed T-shirts. Browse in person, or keep shopping anytime through the app.

    Event website ↗
  • 12pm

    Salsa Lessons for Absolute Beginners! Fall Series! Saturdays @12pm!!

    Glen Burnie · verified Oct 11
    See details

    A new fall series for absolute beginners introduces Salsa 101, taught by BSDC instructor Emily Imber. Lessons focus on foundational steps and hip movement, with each class adding new moves and combinations that build on what was learned before so participants finish with a stronger base in salsa. Attend solo or with a partner, and expect partner rotation in a supportive setting. Single-class attendance is limited to the first two weeks of the session, and continued participation requires monthly enrollment. Pre-registration is required for all classes. Pricing is $30 per class when prepaid online, $35 at the door, or $110 for a four-class pass. Refunds are not provided except if a class is canceled or moved, and transfers to other classes or events are available.

    Event website ↗
  • 1pm

    SUSTO -Solo w. Daniel Ray Hilsinger (Matinee)

    Rams Head On Stage, 25 West St, Annapolis · verified Oct 11
    See details

    Experience a solo matinee from Justin Osborne, the singer, songwriter, and storyteller behind SUSTO, alongside Daniel Ray Hilsinger. Osborne launched SUSTO in 2013 while living in Havana, Cuba, and has since developed a wide-ranging catalog shaped by deeply personal writing and a sound that spans Southern Gothic, folk, rock, country, and psychedelia. In a stripped back setting, his songs step forward, spotlighting voice, lyrics, and narrative craft. The performance offers a personal window into the artist behind work with SUSTO, the Susto Stringband, and his solo performances, touching on themes of love, loss, change, resilience, and the unexpected beauty found in everyday life. Open to all ages.

    Event website ↗
  • 7pm

    Paint Night

    102 Roesler Rd, Glen Burnie · verified Oct 11
    See details

    This first Paint Night offers wine, art, and fun for a creative evening of painting.

    Event website ↗
  • 8pm

    Standup comedy

    Chesepiooc Real Ale Brewery, 2408 Crofton Blvd, Crofton · verified Oct 11
    See details

    Settle in for standup at Chesepiooc Real Ale Brewery as Encore Comedy presents a showcase of comedians from Maryland and across the East Coast. Previous Encore Comedy lineups have included performers with credits at the Comedy Cellar, the Laugh Factory, and Madison Square Garden, writers from SNL and Conan, Kill Tony Golden Ticket winners, writers for The Onion, and comics with Don't Tell and Dry Bar specials. The aim is to bring the energy of a comedy club to a relaxed brewery setting, produced by a group that runs shows throughout the East Coast.

    Event website ↗
  • 8pm

    Weekly Music Bingo Event

    The All American Steakhouse, 1502 Annapolis Rd, Odenton · verified Oct 11
    Free

    Each week, The All American Steakhouse in Odenton hosts a music bingo night with no cost to participate, giving players a chance to test their music knowledge and compete for prizes. Beverage offers include $5 rail drinks, $6 Long Island Iced Teas, and half off domestic drafts. Food specials feature cheesesteaks and fries at 50 percent off. The evening pairs music-themed gameplay with discounted food and drinks.

    Event website ↗
  • 8:30pm

    Coconut Joes

    Coconut Joe's Bar & Grill, 48 South River Road, Edgewater
    See details

    Coconut Joe's Bar & Grill hosts a mix of rock and alternative music that aims to please a variety of tastes. There is something for every kind of listener.

    Event website ↗
Sunday, October 25 5 events
  • 1pm

    Pet Parade

    Historic Hancock's Resolution, 2795 Bayside Beach Rd, Pasadena · verified Oct 11
    Free

    Celebrate animals with a festive pet parade and a day devoted to appreciation. Participants can register their pets in costume to take part in the procession. There will be door prizes, and judges will award additional prizes. Enjoy a long walk in the park with your pet as part of the fun.

    Event website ↗
  • 1pm

    Plant Swap, Costume Contest, & Pumpkin Hunt/Paint

    Hysteria Taphouse, Pasadena · verified Oct 11
    See details

    Anne Arundel County Plant Swap brings its monthly plant exchange to Hysteria Taphouse in Pasadena, Maryland. The gathering features a plant themed costume contest, vendors, and a pumpkin hunt with a chance to paint the pumpkin you find. Plant-or-treating may be included. There will also be a prize claim for summer reading due to September’s cancellation.

    Event website ↗
  • 2pm

    Paint & Sip

    Middleton Tavern, 2 Market Space, Annapolis · verified Oct 11
    See details

    At Middleton Tavern, a relaxed Paint & Sip invites participants to create a scenic painting with guidance from the Red Apron Artist. Attendees can choose their own color palette to personalize the artwork. All net proceeds go to EUMC to benefit Naptown Freedom Schools.

    Event website ↗
  • 3pm

    Puerto Rican Bomba with Sheila Brown

    BSDC Latin, African & Cultural Dance Institute, Glen Burnie · verified Oct 11
    See details

    Experience the energy of Puerto Rican Bomba in Glen Burnie with a hands-on workshop led by Sheila Brown, presented as part of BSDC’s ongoing workshop series. The session explores core rhythms, expressive movement, and improvisation known as piquetes while highlighting the dance’s cultural roots. Expect a 90-minute class that blends technique, musicality, and history with both group and solo practice, creating plenty of space to move and connect with the music. Across the series, participants encounter rhythms such as Sicá, Seis Corrido, Holandés, and Cuembé, with a dedicated time to revisit and celebrate them all. All ages are welcome, and no partner or prior experience is required, making it a welcoming setting for dancers, musicians, and anyone curious about Afro-Puerto Rican culture. A long, full circle skirt is optional and encouraged for those who enjoy dancing with skirts. Ticket options include advance general admission, at-the-door pricing if available, a bring-a-friend offer, a member discount, and a series pass for all three classes. Capacity is limited. Tickets are non-refundable but can be transferred to another attendee with advance notice. Sheila Brown is an Afro-Puerto Rican artist with more than 25 years of experience spanning bomba, plena, salsa, ballet, tap, and jazz. She has trained in Puerto Rico and the United States, performed nationally with companies including Latin Vintage and Iroko, and continues to teach salsa on2 and bomba while honoring the rhythms, history, and Afro-diasporic foundations that shape her work.

    Event website ↗
  • 7pm

    Intimate Jazz presents - The Midiri Brothers Trio

    49 West Coffeehouse, Winebar & Gallery, 110 Cathedral St, Annapolis · verified Oct 11
    See details

    Intimate Jazz at 49 West Coffeehouse, Winebar & Gallery in Annapolis presents The Midiri Brothers Trio, reuniting clarinetist and saxophonist Joe Midiri, drummer and vibraphonist Paul Midiri, and pianist Joe Holt. The three first met in high school in the 1970s and soon formed their first band, and they have stayed connected ever since, marking more than fifty years of making music together. The Midiri Brothers built a career in classic jazz, and an All About Jazz reviewer compared their trio to the storied Benny Goodman, Gene Krupa, and Teddy Wilson combo, calling Joe Midiri’s clarinet a worthy heir to Goodman’s legacy. Cover charge is $25, and reservations are available by phone at 410-626-9796.

    Event website ↗
Monday, October 26 2 events
  • 10:30am

    Art and Story Time

    Chesapeake Children's Museum, 25 Silopanna Rd, Annapolis · verified Oct 11
    See details

    Mrs. Spears and Puppy the puppet host a playful session filled with stories, songs, and hands-on art activities. It is created with babies, toddlers, and preschoolers in mind, and welcomes their grown-ups too. Families can connect with others, make new friends, and share memorable moments together.

    Event website ↗
  • 6pm

    Masada-Ween 2026

    160 Ritchie Hwy, Severna Park · verified Oct 11
    See details

    Masada offers a weeklong Halloween celebration with challenges that test skills, spirit, and determination. In the days leading up to Halloween, participants receive a challenge card at the start of the week, then tackle each task, mark their progress, and aim to finish the full card before the week ends. Completing every challenge earns an exclusive Masada-Ween shirt available only to those who complete the entire set.

    Event website ↗
Tuesday, October 27 1 event
  • 1pm

    First Annual Fall Fest

    Full Circle Home Care , 2131 Espey Ct, Crofton · verified Oct 13
    See details

    Full Circle Home Care is hosting a first annual community fall fest held entirely indoors, created to welcome all ages and abilities. Families, friends, neighbors, and community groups can enjoy candy, non-food treats, interactive tables and activities, and plenty of chances to connect. Costumes are optional. The celebration is rain or shine, and the format is drop in, with RSVP encouraged and walk ins welcome. An information table will be available where the team shares details about home care and adult developmental disability services. Community partners, CCS professionals, support planners, and social workers can stop by a dedicated welcome area for a small token of appreciation, refreshments, and service information, with time to chat and explore collaboration. Colleagues and the individuals and families they support are welcome to attend. Groups can coordinate arrival or inquire about hosting a table or activity. Hosts bring their own decorations, treats, and activity supplies, and are encouraged to have brochures, flyers, business cards, and other materials on hand. Participation and setup will be confirmed by the organizer. Donations are appreciated, including individually wrapped candy, non food treats, decorations, activity supplies, bottled water, and printing or event supplies. Children must attend with a parent or responsible adult. Individuals who need personal support should attend with a caregiver or support staff. For accessibility needs, arrangements can be discussed in advance.

    Event website ↗
Wednesday, October 28 4 events
  • 10am

    DOWNS PARK, WILD READ

    P.O. Box 881, Pasadena, MD, 8327 Baltimore Annapolis Blvd, Pasadena · verified Oct 11
    See details

    This adult-focused book club gathers in the Chesapeake Room at Downs Park to discuss a variety of books about nature, wildlife, conservation, and environmental issues. Participants explore different perspectives on the natural world and engage in conversation with fellow readers.

    Event website ↗
  • 3:30pm

    Cleveland Golf Wedge Clinic

    Compass Pointe Golf Courses, 9010 Fort Smallwood Rd, Pasadena · verified Oct 11
    See details

    Take part in a wedge clinic at Compass Pointe Golf Club. Each participant receives one custom fit Cleveland RTZ2 wedge, fitted by a Cleveland Golf representative, along with instruction led by Stephen Herschel, Director of Instruction at Compass Pointe. The cost is $199 per person. Attendees can also access special pricing on additional wedges. Registration is required and space is limited.

    Event website ↗
  • 5pm

    One Step Down

    Rams Head Dockside, 1702 Furnace Dr, Glen Burnie · verified Oct 11
    See details

    One Step Down brings a soulful acoustic set to Rams Head Dockside in Glen Burnie. Joe Puleo on guitar and Karen Leaf on vocals deliver a broad mix of cover songs that reaches across decades and genres. The waterfront, beach-like setting complements the performance, creating a relaxed atmosphere suited to live music and a bite to eat.

    Event website ↗
  • 5:30pm

    Sparks Solo

    Nonna Angela's Italian Bistro & Wine Bar, 2225 Defense Hwy, Crofton · verified Oct 11
    See details

    Sparks presents a monthly solo performance at Nonna Angela's Italian Bistro & Wine Bar. This recurring appearance takes place in a traditional-style Italian bistro and wine bar setting.

    Event website ↗
Thursday, October 29 4 events
  • 5pm

    MNADV's 45 Year Celebration & Annual Awards Celebration

    BWI Airport Marriott, 1743 W Nursery Rd, Linthicum Heights · verified Oct 11
    See details

    MNADV marks 45 years of advocacy with a milestone celebration and annual awards program at the BWI Airport Marriott. For more than four decades the organization has promoted safety, justice, and healing for survivors of intimate partner violence across Maryland, and this gathering shines a light on the people, programs, and partnerships that have strengthened the movement and changed lives statewide. The program features a VIP reception followed by an awards ceremony recognizing outstanding contributions in the field. It brings together advocates, survivors, community partners, policymakers, and supporters to honor past progress and celebrate the future of this work.

    Event website ↗
  • 6:30pm

    Candlelight: 90s Unplugged

    Maryland Hall, 801 Chase St, Annapolis
    See details

    In Annapolis, Maryland Hall hosts an intimate Candlelight concert that shines a light on 90s unplugged favorites in a warm, multi-sensory setting. Performed by the Listeso String Quartet and set under the gentle glow of candlelight, the 60 minute program features acoustic-leaning hits such as Everlong, Don't Speak, Zombie, Ironic, Wonderwall, High and Dry, Enter Sandman, Under the Bridge, Fly Away, Hallelujah, Tears in Heaven, and Smells Like Teen Spirit. Doors open 45 minutes before the performance, and no late entry is allowed once it begins. Seating is assigned within each zone on a first come, first served basis. Guests must be 8 or older, and anyone under 16 must be accompanied by an adult. The venue is ADA compliant.

    Event website ↗
  • 7pm

    Anton at Primo!

    Primo Pasta Kitchen, 8557 Fort Smallwood Rd, Pasadena · verified Oct 11
    See details

    Primo Pasta Kitchen in Pasadena hosts a night with Anton Tuvelman, a dynamic solo performer who turns the room into an interactive musical experience. With high energy and rich, layered sound built through live looping, he re-creates favorites, reimagines classics, and blends unexpected combinations you will not find elsewhere. The audience steers the set through spontaneous requests across decades and styles, and he frequently attempts songs he has not performed before, expanding the repertoire in real time. Expect a tailored, immersive show where surprises are part of the fun and the crowd helps shape every moment.

    Event website ↗
  • 8:45pm

    Candlelight: A Haunted Evening of Halloween Classics

    Maryland Hall, 801 Chase St, Annapolis
    See details

    Maryland Hall sets the stage for an evening of Halloween‑inspired music performed by the Listeso String Quartet from Annapolis, all within the gentle glow of candlelight. The tentative program spans pop, film, and classical favorites, with selections such as Thriller, Funeral March of a Marionette, a movement from Shostakovich’s String Quartet No. 8, Tubular Bells from The Exorcist, themes from Stranger Things, Beetlejuice, The Addams Family, Halloween, and Psycho, along with Ghostbusters, Saint‑Saëns’s Danse macabre, Mussorgsky’s Night on Bald Mountain, the Time Warp from The Rocky Horror Picture Show, and a medley from The Nightmare Before Christmas. The venue is ADA compliant. Attendees must be at least 8 years old, and anyone under 16 must be accompanied by an adult. Seating is assigned upon arrival within each zone on a first come, first served basis.

    Event website ↗
Friday, October 30 3 events
  • 11am

    Trick Or Treat

    Elvaton Park Offices, 8221 Ritchie Hwy, Pasadena · verified Oct 11
    Free

    Celebrate a community trick-or-treat at Elvaton Park Offices. Children of all ages can collect candy and other goodies, and non-food treats will be available for those who avoid candy in support of the Teal Pumpkin Project. There is no cost to attend and everyone is welcome. To help with planning, attendees are asked to sign up and share how many people will be in their group so there are plenty of treats to go around. The festivities also help launch DCA’s Annual Holiday Toy Drive with the Kamryn Lambert Foundation. Staff from Douglas Realty, Coastline Mortgage, and Admiral Title hold a company costume contest, and every vote adds a one dollar donation to the drive, boosting the opening collection. Toy donations are encouraged, and trick-or-treaters can bring an item to contribute as collections begin across Douglas, Coastline, and Admiral locations.

    Event website ↗
  • 7pm

    Scream Skate!

    1082 State Route 3 S, Gambrills · verified Oct 11
    See details

    Skate first, scream later at a Halloween skate in the spirit of your favorite scary movies. Scream Skate at Skate Zone Crofton includes games and a Best Dressed contest. Attendees are encouraged to wear their scariest costumes and lean into the spooky vibe. What is your favorite skate movie?

    Event website ↗
  • 9pm

    Life After Dinosaurs

    Blackwall Hitch, 400 6th St, Annapolis · verified Oct 9
    See details

    Life After Dinosaurs brings live music to Blackwall Hitch Annapolis, alongside dinner and drinks.

    Event website ↗
Saturday, October 31 5 events
  • 9am

    APRIL'S 9TH ANNUAL 3 MEN & LADY TOURNAMENT LIMIT 2100

    Brews & Cues On The Blvd, 7954 Baltimore Annapolis Boulevard, Glen Burnie · verified Oct 11
    See details

    Teams of four compete in a double elimination 3-men-and-1-lady format with a team cap of 2100 at Brews & Cues On The Blvd in Glen Burnie, Maryland. The entry fee is $240 per team, paid at the door, and every participant must have a minimum robustness of 300 with no exceptions. This Halloween edition encourages costumes, and a special prize will be awarded to the best team costume, though dressing up is optional. Play includes 8-ball, 9-ball, and 10-ball, with no short games. Scoring is straightforward… each game won by a man counts for one point and each game won by a woman counts for two, and the team with the most points wins the match. Time-outs are allowed only during the ladies’ games, and RYO applies. If a match ends level, the tiebreaker is a single game of 9-ball triples capped at 1550 in which one of the three shooters must be the woman. Players must remain in rotation or it is a ball-in-hand foul. Rules by discipline are as follows. 8-ball uses BCA rules. In 10-ball, players call the pocket with an option, push-outs are in play, and jump cues are permitted. In 9-ball, only the 9 needs to be called, and both push-outs and jump cues are allowed. Matches may be assigned to two tables when available at the tournament director’s discretion, and a second day will be used if necessary.

    Event website ↗
  • 10am

    SNT's Trunk or Treat & Vendor Event

    Green Haven, Green Haven · verified Oct 11
    Free

    Enjoy a festive, family-friendly celebration at Green Haven featuring trick or treating from decorated car trunks and vendor booths. Children can gather plenty of candy while shoppers browse vendor stalls. Costumes are welcome, and the activities are designed for all ages. Admission is free.

    Event website ↗
  • 11am

    Tavern Talk: Inside Annapolis’s Revolutionary-Era Taverns

    Hogshead Trades Museum, 43 Pinkney St, Annapolis · verified Oct 11
    See details

    At Hogshead Trades Museum, explore tavern life in Annapolis during the Revolutionary era. Living historian Jacob Kirsch shares how taverns were more than places for food, drink, and lodging, serving as hubs for news, conversation, and community. Enjoy seasonal cider, watch a turnip carved for Halloween, and learn about other tavern customs. This drop in program features informal interaction and demonstrations. Visitors may arrive at any time during program hours and move through at their own pace. Admission is free, with a suggested donation of $5. Advance registration is recommended but not required.

    Event website ↗
  • 7pm

    Gospel Glow Skate Night!

    1082 State Route 3 S, Gambrills · verified Oct 11
    See details

    This glow-themed skating session focuses on community and faith. Colorful lights set the mood while Gospel and Christian music plays throughout. Positioned as an option instead of traditional Halloween festivities, it welcomes families, friends, and church groups to share time together on the rink. Advance purchase is required and tickets are available online only.

    Event website ↗
  • 9pm

    24 Karat Halloween Party

    Copper Creek Pub & Ale House, 904 Governor Ritchie Hwy, Severna Park · verified Oct 11
    See details

    This Halloween celebration marks the final show, serving as a grand sendoff. A live band will perform, and food and drinks will be available. Costumes are encouraged to keep the celebration going.

    Event website ↗
Sunday, November 1 4 events
  • 8:30am

    Little Leapers at Sky Zone Gambrills

    986 Waugh Chapel Way, Gambrills · verified Oct 11
    See details

    Little Leapers at Sky Zone Gambrills is a dedicated jump session for children ages 6 and under, giving young movers space to bounce, play, and explore with parent participation welcome. Sky Socks are required. The first accompanying adult is free, and a second adult can join for $5. Basic and Elite members can attend at no additional charge.

    Event website ↗
  • 11am

    Annapolis First Sunday Arts Festival

    Calvert and West Streets, 63 West St, Annapolis · verified Oct 12
    Free

    The Annapolis First Sunday Arts Festival is a free outdoor art market celebrating local and regional creativity with live music and plentiful nearby dining. Set along West Street and Calvert Street in the Annapolis Arts District and the city’s historic district, it offers the chance to meet makers and purchase their work directly. Shoppers often discover paintings, photography, wheel-thrown pottery, fused glass and blown glass, jewelry, woodturning, sculpture, fiber arts, candles, home decor, and more, while restaurants serve flavors of Maryland alongside other culinary favorites. Parking is available at the Calvert Street Parking Garage and the Whitmore Parking Garage. Calvert Street will be closed for the festival. Friendly leashed pets are welcome, with a reminder that pavement can become very hot during summer months. The festival is held on the first Sunday of the month from May through November and is presented by the Inner West Street Association.

    Event website ↗
  • 11:30am

    Honoring Maryland’s Emancipation Day at the Museum of Historic Annapolis

    Museum of Historic Annapolis, 99 Main St, Annapolis · verified Oct 9
    See details

    Maryland marked the end of slavery when its 1864 constitution took effect, and the Museum of Historic Annapolis is commemorating that milestone with a full day of special programs and interactive activities included with admission. Guided tours focus on African American history, honor Maryland’s Emancipation Day, and share the stories of African American community leaders in Annapolis. Families can enjoy a hands-on craft and browse a Book Nook featuring children’s titles curated with support from the Anne Arundel County Public Library. The program features presenter Briayna Cuffie, a civil servant who also works as a public historian, genealogist, and strategist outside regular work hours. Tours are included with museum admission. General admission is $7, and entry is free for Historic Annapolis members and for children age 7 and under. Advance registration is encouraged.

    Event website ↗
  • 1:30pm

    Earth Care: Meditation Garden Planting!

    Prince of Peace Presbyterian Church, 1657 Crofton Pkwy, Crofton · verified Oct 11
    Free

    The event centers on creating a Meditation Garden at the corner of Ardsley Place by planting native species and placing a bench for quiet reflection. Plants will come from a combination of Unity Gardens Grant funding, Creation Care budget support, and relocations from other parts of the church grounds. A limited supply of tools and gloves will be available, so bringing personal gardening gear is recommended. Lemonade, water, and light snacks will be provided.

    Event website ↗
Tuesday, November 3 2 events
  • 10am

    Here's to Heroes!

    The Spice & Tea Exchange of Annapolis, 155 Main St, Annapolis · verified Oct 11
    See details

    The Spice & Tea Exchange celebrates community heroes on the first Tuesday of every month with in-store savings. Firefighters, police officers, first responders, military personnel, and teachers receive 30 percent off all food items. A valid ID is required to redeem the discount. This offer cannot be combined with other promotions, coupons, or sales. If any part of a discounted purchase is returned, the savings will be forfeited or the equivalent amount will be deducted.

    Event website ↗
  • 7:30pm

    PFLAG Annapolis/AACo Support Meeting

    Unitarian Universalist Church of Annapolis, 333 Dubois Rd, Annapolis
    See details

    The PFLAG Annapolis/AACo Support Meeting offers three concurrent groups tailored for different needs: youth, adults, and parents and allies. It is held at the Unitarian Universalist Church Annapolis, not in the FAHS House behind the church. The adult group meets in rooms on the ground floor, while the youth and the parents and allies groups gather on the main floor. For the adult group, enter from the parking lot through the double green doors. For the youth and parents and allies groups, use the main entrance.

    Event website ↗
Wednesday, November 4 4 events
  • 5:30pm

    McCoy Solo at Nonna Angela's Italian Bistro & Wine Bar!

    Nonna Angela's Italian Bistro & Wine Bar, 2225 Defense Hwy, Crofton
    See details

    Enjoy an evening with Steve featuring music and food.

    Event website ↗
  • 6pm

    Monthly Pregnancy Support Group

    836 Ritchie Hwy, Severna Park · verified Oct 11
    Free

    This free community group offers a welcoming space for birthing people, partners, and even older siblings to connect, ask questions, and build a strong support network. Each gathering focuses on a monthly theme, and participants are encouraged to share experiences and engage in open conversation within a judgment free setting. Topics may include preparing for birth in the age of overwhelming online information with Sarah Austin, prenatal movement to support the physical demands of labor with a prenatal yoga instructor, pelvic floor care before, during, and after birth with a pelvic floor physical therapist, and feeding your baby by breast, bottle, or anything in between with a lactation consultant. Additional conversations may cover postpartum planning and meaningful self care with Jordyn Bell, Licensed Clinical Professional Counselor and perinatal mental health expert, pregnancy nutrition with a nutritionist, and techniques for calming the nervous system for birth, postpartum, and beyond with Sarah Austin. Guest speakers may be announced as they are confirmed, and topics can shift based on availability. Because the facilitator is an active birth worker, sessions may occasionally be canceled or rescheduled due to clients in labor.

    Event website ↗
  • 6pm

    Fall Bushel Basket Planter

    244 Old Mill Bottom Rd S, Annapolis · verified Oct 11
    See details

    At Ridge Grow, participants craft a cozy fall bushel basket planter featuring seasonal plants, varied textures, and autumn color. The workshop fee is $70 per person. Admission includes a bushel basket, seasonal plants, soil, and all required supplies, along with step-by-step guidance so everyone departs with a completed arrangement ready for a porch or entryway. Capacity is limited to 12 participants and advance registration is required. Beverages and light snacks are provided during the session. Plant varieties and colors may vary based on availability.

    Event website ↗
  • 8pm

    Gaelic Storm

    Rams Head On Stage, 25 West St, Annapolis · verified Oct 11
    See details

    Gaelic Storm delivers a powerhouse Celtic show shaped by decades on the road. With more than two thousand performances behind them, this multi-national band has become a formidable live act, celebrated for vivid storytelling, driving instrumentals, and a blend of Irish tradition and fresh invention that appeals to listeners across genres. Their career began in the mid-1990s as a pub band in Santa Monica, a start that soon led to an appearance in Titanic performing Irish Party in Third Class. Since then they have reached the top of the Billboard World chart six times, played major mainstream festivals, and frequently headlined large Irish festivals around the United States. The group keeps a blue-collar touring ethic that continually sharpens the show and reflects a strong commitment to the fans who fuel it. Recent additions Natalya Kay on fiddle and Parker Hastings on guitar bring new energy and musicianship to the lineup. This event is open to all ages.

    Event website ↗
Thursday, November 5 2 events
  • 6:30pm

    Creative Circle - Monthly Meetup (2026)

    ArtFarm Studios, 111 Chinquapin Round Rd, Annapolis · verified Oct 11
    See details

    Connect with fellow creators in a monthly meetup that blends art-making, conversation, and experimentation. Drop in for a single class or take part in all five sessions. No prior experience is needed, only a willingness to get out of the house, try new things, and have fun. Guided by Creative Kate, an art coach, each gathering starts with an optional warm-up to shake off the week, a surprise material to spark ideas, a meaty prompt to explore, tips for continuing at home, and a step-by-step path that lets you choose how much guidance you want. Every session introduces a different medium and fresh challenge, so each meetup feels new. Past activities have included mystery-box projects, black and white pieces using ink and even salt and pepper, bedazzled resin jewelry with a futuristic flair, circular weaving, tiny clay foods, and more. This semester brings pop-up creations, iron-on wall fabric, mosaics, upcycling projects, and take-home prompts to keep creativity flowing. Participants frequently describe the experience as a therapeutic reset and appreciate the calm, supportive teaching style and low-pressure environment. You can also bring your own work-in-progress to stay accountable to personal goals. All art forms are welcome, with the exception of oil and spray paints. The studio offers a variety of supplies to experiment with, plus peer feedback and help getting past creative blocks like the blank page. Due to small class sizes and advance planning, missed classes are not refundable. If a class has a waitlist and your spot can be filled, a refund may be issued. Masks are optional for indoor classes and events, and ArtFarm may update its mask policy with advance notice if anything changes.

    Event website ↗
  • 8pm

    Gaelic Storm

    Rams Head On Stage, 25 West St, Annapolis
    See details

    Gaelic Storm brings its high-energy Celtic sound to Rams Head On Stage in an all ages performance. With more than two decades on the road and over two thousand shows, this multinational group is known for vivid storytelling, driving instrumentals, and a strong link to tradition that speaks to fans of many genres. Their work ethic and commitment to their audience define their live show, built through constant touring across the United States and abroad. The journey started as a Santa Monica pub band in the mid 1990s and soon included a memorable appearance in the film Titanic performing Irish Party in Third Class. Since then they have topped the Billboard World chart six times, played major mainstream festivals, and often led the bill at large Irish festivals nationwide, blending Celtic roots with inventive Irish rock. Recent lineups feature Natalya Kay on fiddle and Parker Hastings on guitar.

    Event website ↗
Friday, November 6 4 events
  • 6:30pm

    The Artist's Table

    2111 Baldwin Ave, Crofton
    See details

    Settle at a shared table for unhurried creativity with thoughtfully crafted tea and friendly faces. Sketch, paint, color, or work with favorite materials, and feel free to use the supplies provided. The environment is relaxed with no pressure or expectations, focusing on the simple joy of making art alongside others. This monthly gathering creates space to slow down, craft by hand, and connect with fellow artists and creatives. Drop in at your convenience. Admission is free, and optional donations support room rental and supplies. Hosted by STRŌB Apothecary.

    Event website ↗
  • 6:30pm

    Magothy CA$H BINGO

    Severna Park Elks Lodge, 160 Truck House Rd, Severna Park · verified Oct 11
    See details

    Returning after last year’s fun, this annual cash bingo night brings a lively evening in support of a preschool at Severna Park Elks Lodge in Severna Park, MD. Tickets are available, and individuals or businesses can sponsor a round to further support the cause. Appreciation is extended to everyone whose generosity helps make it possible.

    Event website ↗
  • 7pm

    Live Music : Dave & Jenn of Ginger & the Protest at Pit Stop Pub

    Pit Stop Pub, 8111 Fort Smallwood Rd, Curtis Bay · verified Oct 11
    Free

    Pit Stop Pub hosts an acoustic set from Dave and Jenn, filling the room with cozy fall energy. Look forward to food, refreshing drinks, and a mix of popular favorites. There is no cover charge, making it an easy stop for a relaxed night of live music.

    Event website ↗
  • 10pm

    Noelle & Jeff Band

    Middleton Tavern, 2 Market Space, Annapolis · verified Oct 11
    See details

    Middleton Tavern hosts the Noelle & Jeff Band for a high energy night packed with nostalgic favorites from the 90s and 2000s plus a few 80s classics, all primed for big sing alongs. Jeremy and Mike join the lineup for a louder, rowdier set with a playful edge. Expect continuous live music and an upbeat atmosphere. There is no cover.

    Event website ↗
Saturday, November 7 13 events
  • 8am

    Early Christmas Flea Market and Craft Fair 2026 at the Benson-Hammond House

    7101 Aviation Blvd, Baltimore · verified Oct 11
    See details

    Kick off holiday shopping with an early Christmas market and craft fair at the Benson-Hammond House. Vendors will be set up across the grounds with plenty to browse and buy. It is a simple way to support local small businesses, artisans, and other vendors. Those interested in selling can find an application on the website under the Events section. Please note that it takes place on the first Saturday of the month.

    Event website ↗
  • 8am

    AutumnFecht 2026

    740 State Route 3 S, Gambrills · verified Oct 11
    See details

    AutumnFecht 2026 is a one day event in Gambrills, MD focused on classes and sparring, hosted by Maryland KdF. It features unconventional classes, a welcoming atmosphere, and plenty of sparring.

    Event website ↗
  • 8am

    SPAN Turkey Trot 2026 - Join the SPUMC Team!

    Kinder Farm Park Rd, Millersville, MD 21108, United States, 1064 Kinder Farm Park Rd, Millersville · verified Oct 11
    See details

    Step out for a meaningful cause at SPAN’s Turkey Trot at Kinder Farm Park in Millersville. Take part by running, walking, or cheering from the sidelines as the community rallies support for neighbors through SPAN. When registering, select the team named Severna Park UMC to participate with the SPUMC team.

    Event website ↗
  • 9am

    PUMC Craft Fair

    61 Governor Ritchie Hwy, Pasadena · verified Oct 11
    See details

    Pasadena United Methodist Church hosts its annual craft fair featuring craft vendors and homemade soup.

    Event website ↗
  • 9am

    Stride for SPAN 14th Annual Turkey Trot 5K/1M

    Kinder Farm Park Rd, Millersville, MD 21108, United States, 1064 Kinder Farm Park Rd, Millersville · verified Oct 11
    See details

    The 14th annual Stride for SPAN Turkey Trot brings a 5K and a 1 mile fun run or walk to Kinder Farm Park in Millersville, MD. Participants can choose their distance and enjoy a friendly community experience on the park grounds. Groups of four or more can take advantage of social team pricing.

    Event website ↗
  • 10am

    Adopt A Lab Day

    PetSmart, 2601 Housley Rd, Annapolis
    See details

    At PetSmart Annapolis Maryland #0359, this adoption event gives prospective adopters the chance to meet participating dogs and take steps toward welcoming a new family member. The organizers host similar events throughout the year in Virginia and Maryland, and because these gatherings can draw strong interest, they share guidelines to keep everything running smoothly. Review the organizer’s website in advance to understand the process and confirm what you may need to bring.

    Event website ↗
  • 10am

    Lessons from Nature for Children: Carrying Love through the Seasons

    John and Cathy Belcher Campus, 90 Governor Ritchie Hwy, Pasadena · verified Oct 12
    See details

    This quarterly, nature-focused gathering serves children and teens ages 6 to 18. Through hands-on art-making, calm outdoor activities, and guided moments of reflection, participants explore emotions and honor loved ones. The session is facilitated by Marie Burgess, a grief therapist, nature-informed therapist, and hospice volunteer. Light snacks are provided and the program is free. It takes place on the John & Cathy Belcher Campus in Pasadena, Maryland. Registration for most programs can be completed by calling 1-888-501-7077 or emailing griefinfo@chesapeakelifecenter.org.

    Event website ↗
  • 10am

    NHS PTSA 2026 Fall Craft Fair

    1121 Duvall Hwy, Pasadena · verified Oct 11
    See details

    The Northeast High School PTSA Fall Craft Fair offers a festive shopping experience with local vendors and holiday touches. Explore handmade gifts, home decor, boutique finds, jewelry, baked treats, and other seasonal favorites. Get a head start on holiday gift lists while supporting the Northeast High School PTSA. Vendor registration is open to all, and vendor spotlights, event updates, and sneak peeks will be shared in advance of the fair.

    Event website ↗
  • 11am

    Loaves and Ladles Meal ministry

    117 Ferndale Rd, Glen Burnie · verified Oct 11
    Free

    Open to all, this meal ministry offers a complimentary hot meal paired with welcoming conversation, creating space for fellowship, compassion, and connection. It is held in the fellowship hall at Ferndale United Methodist Church.

    Event website ↗
  • 12pm

    Indie Author Pop Up Event

    Marley Station Mall, 7900 Ritchie Hwy, Glen Burnie · verified Oct 11
    Free

    This free event features 30 authors and puts a spotlight on supporting them.

    Event website ↗
  • 1pm

    Temple Owls at Navy Midshipmen Football

    Navy-Marine Corps Memorial Stadium, 550 Taylor Ave, Annapolis
    See details

    Temple travels to Annapolis for a meeting with Navy at Navy-Marine Corps Memorial Stadium, bringing FBS college football to a distinctive setting. The matchup highlights differing philosophies, with Temple prioritizing control at the line of scrimmage and Navy relying on a disciplined, assignment-focused approach. Field position and sharp execution could swing the result in a hurry as momentum shifts from series to series.

    Event website ↗
  • 6:30pm

    Pasadena, MD- "Paint Your Pet" Night

    3201 Mountain Rd, Pasadena · verified Oct 11
    See details

    Head to Hysteria Taphouse for a hands-on paint night where participants create a custom portrait of their own pet, enjoy a pint, and meet adorable puppies and dogs. Artist Sheena Herron from Create with Art & Soul will guide each step and can offer alternate project designs for anyone who prefers something other than a pet portrait. Raffles and giveaways add to the fun. Tickets are 40 dollars per person, and a portion of each sale benefits Operation Paws for Homes. To ensure a personalized canvas, a photo of your pet is required at registration, and pets of all kinds are welcome, including dogs, cats, birds, and reptiles. Your instructor will sketch your pet in advance. For questions about the painting portion, call 443-902-6106. Adoptable dogs and cats are expected to attend, and the lineup may change as animals find homes.

    Event website ↗
  • 7pm

    LIVE MUSIC with Brandt

    Blackwall Barn & Lodge - Gambrills, 329 Gambrills Rd, Gambrills · verified Oct 11
    See details

    Enjoy dinner and drinks accompanied by live music at The Barn & Lodge.

    Event website ↗
Sunday, November 8 2 events
  • 9am

    Psychic Affairs of Maryland - November 2026

    Bowie Elks Lodge #2309, 1506 Defense Hwy, Gambrills
    See details

    At Bowie Elks Lodge #2309, Psychic Affairs of Maryland presents a one-day gathering devoted to exploration and connection. Meet intuitive readers for personal sessions with psychics, mediums, and tarot practitioners. Experience energy work intended to support balance and clarity, then browse a variety of metaphysical vendors offering crystals, jewelry, herbs, and handcrafted items. The atmosphere is welcoming to both longtime spiritual seekers and first-time explorers. Take your time, engage in conversations, and discover what messages or insights may be waiting for you.

    Event website ↗
  • 10am

    Home Defense

    160 Ritchie Hwy, Severna Park · verified Oct 11
    See details

    Build a safer home by learning how to spot weaknesses before a crisis occurs. This course helps participants evaluate vulnerabilities in their home, identify potential security concerns, and develop a clear plan for home defense and preparedness. It also explains how Maryland laws apply to self-defense within the home, offering guidance on legal responsibilities and protections. A practical segment covers movement inside a structure, focusing on footwork, positioning, the geometry of rooms and hallways, and how different angles affect visibility and exposure.

    Event website ↗
Tuesday, November 10 1 event
  • 4pm

    Ledo Pizza Spirit Night

    Ledo Pizza, Crofton · verified Oct 12
    See details

    Guests who order takeout or dine in at Ledo Pizza in Crofton will have a portion of sales donated. Attendees can also sign in for a chance to win a new bike courtesy of Crofton Family Bike Shop.

    Event website ↗
Wednesday, November 11 1 event
  • 5:30pm

    Sparks Solo at Nonna Angela's Italian Bistro & Wine Bar

    2225 Defense Hwy, Crofton
    See details

    Sparks presents a monthly solo performance at Nonna Angela's Italian Bistro & Wine Bar, a traditional-style Italian bistro and wine bar.

    Event website ↗
Thursday, November 12 3 events
  • 3am

    Fall Harvest Weekend Crop

    Hampton Inn & Suites by Hilton Annapolis, 124 Womack Dr, Annapolis
    See details

    CropIt! Escapes hosts a Fall Harvest Weekend Crop in Annapolis, MD. Across four days, participants can focus on scrapbooking and creative projects, take time to unwind, and enjoy the company of fellow creatives. Registration is open.

    Event website ↗
  • 3pm

    Fall Harvest Weekend Retreat

    Hampton Inn & Suites by Hilton Annapolis, 124 Womack Dr, Annapolis
    See details

    CropIt! Escapes is hosting a Fall Harvest Weekend Crop in Annapolis, Maryland, offering a relaxed retreat for scrapbookers. Participants can dive into dedicated time for crafting, share inspiration with fellow creators, and turn favorite moments into keepsakes in a warm, creative setting.

    Event website ↗
  • 7pm

    Crystal Ashram Monthly Meditation

    Annapolis Friends Meeting, Quakers, 351 Dubois Rd, Annapolis · verified Oct 11
    See details

    Settle into a calming sound bath at Annapolis Friends Meeting, Quakers, where a sound frequency specialist from the Human Activation School of Expanded Consciousness guides a gentle immersion with rare Tibetan singing bowls, including instruments more than two centuries old. This non-religious gathering welcomes first-timers and encourages comfort, so bring pillows, blankets, and a yoga mat, and choose to sit, lie down, or stand as the tones unfold. Each month brings a fresh focus, from chakra centered meditations and gong baths to unique themes that honor the natural world, including whales and elephants. After the shared experience, a contemplative conversation invites quiet reflection. A sliding scale contribution of 20 to 40 dollars is suggested, and proceeds support the Crystal Ashram 501(c)(3) nonprofit.

    Event website ↗
Friday, November 13 2 events
  • 7pm

    Laughs in the Lounge

    Stan & Joe's Saloon, 37 West St, Annapolis · verified Oct 9
    See details

    Beer Run Comedy brings its monthly stand up series to the Lounge at Stan and Joe's Saloon in Annapolis, featuring a headlining set from Steve Tracy, whose credits include The Port Comedy Club, Hammerjokes, and Beer Run Comedy. Tickets are $20 online. Guests must be 21 or older, and there is a two item minimum per person. Beer Run Comedy is led by Ray Jubela and Steve Tracy and is active throughout the DC, Maryland, and Virginia comedy scene.

    Event website ↗
  • 7pm

    Remedy @ Perry's 1210 Annapolis Rd, Odenton, MD 21113

    Perry's Restaurant, 1210 Annapolis Rd, Odenton · verified Oct 11
    See details

    Remedy takes the stage at Perry's Restaurant in Odenton, with a halftime show from Brandon Freelump.

    Event website ↗
Saturday, November 14 7 events
  • 9am

    Chesapeake High school Fall Vendor Event

    Chesapeake High School PTSA, 4798 Mountain Road, Pasadena · verified Oct 11
    See details

    Wild Rose Jewelry Co. will be at the Chesapeake High School Fall Vendor Event with favorite pieces and fresh handmade designs. Attendees can explore everything from everyday studs to bold statement earrings to suit a range of styles. The day focuses on shopping local and supporting small businesses, with more to enjoy throughout The Avenue.

    Event website ↗
  • 10am

    Illuminate Annapolis Mind-Body-Spirit-Arts Festival

    Anne Arundel Community College, Arnold
    Free

    At Anne Arundel Community College, a festival celebrates local holistic wellness and the arts. Exhibitors may feature aura photography, bodywork, energy healing, and intuitive readings, from tarot to astrology, alongside handcrafted jewelry, gift items, spa products, and free workshops. Admission is free.

    Event website ↗
  • 10am

    Chesapeake High School Craft Fair

    Pasadena · verified Oct 11
    See details

    Kick off holiday shopping at the Chesapeake High School Craft Fair, where local vendors will be set up both indoors and outdoors. Among the offerings, a vendor stationed outside near an entrance will feature more than 40 seasoning blends, with aromas available to sample before purchasing.

    Event website ↗
  • 10am

    Modern Mama Tees & Co. at Chesapeake High School

    Pasadena · verified Oct 11
    See details

    Modern Mama Tees & Co. will be on site at the Chesapeake High School Fall Event with a curated selection of boutique fashions and graphic T-shirts. Shop the collection in person, or keep browsing later through the app. For vendor inquiries, please reach out to the event organizer, as Modern Mama Tees & Co. is participating solely as a vendor and is not handling sign ups.

    Event website ↗
  • 7pm

    Veterans Holistic Health Fair

    American Legion, 1707 Forest Dr, Annapolis · verified Oct 9
    Free

    Veterans Holistic Health Fair marks the launch of New Mission: Whole Veteran, a program devoted to supporting the mental, physical, and spiritual well-being of those who have served. Taking place at the American Legion in Annapolis, MD, the fair highlights offerings from Body & Brain with Qi Gong and Tai Chi, Velta Moore's Master Honest Beauty with acupressure, Bon AppéSweet with healthy desserts, Mighty Boards with Games For Good, and Sycamore Chaplain Corps with interfaith spiritual counseling. Massage therapy and Reiki energy healing are also represented. Tickets are free for veterans, with discounted options available for family members and caregivers.

    Event website ↗
  • 8pm

    Comedian Paul Mecurio

    Rams Head On Stage, 25 West St, Annapolis
    See details

    Emmy and Peabody honoree Paul Mecurio presents a comedy show. Recognized for his work on The Daily Show with Jon Stewart and for frequent appearances on The Late Show with Stephen Colbert, he has also delivered his own comedy specials. Beyond the stage, he is an actor, an award-winning writer, and the host of the podcast Inside Out with Paul Mecurio, which has earned critical praise. He is also a regular commentator on major news and sports outlets such as CNN, MSNBC, CBS Sunday Morning, Fox News, HLN, and ESPN. This event is for ages 18 and over.

    Event website ↗
  • 8:30pm

    Molloy's Irish Pub

    Molloy's Irish Pub, Gambrills
    See details

    Molloy's Irish Pub hosts live music.

    Event website ↗
Sunday, November 15 3 events
  • 9am

    Modern Mama Tees & Co. at The Station

    45 W Earleigh Heights Rd, Severna Park · verified Oct 11
    See details

    Modern Mama Tees & Co. is appearing as a vendor at The Station Vendor Event, showcasing the newest boutique styles and graphic tees. Browse in person, and keep shopping anytime through the app. Please note that Modern Mama Tees & Co. is a vendor only and does not accept applications or serve as the point of contact for event registration.

    Event website ↗
  • 9am

    OVFC First Responder 5k

    1425 Annapolis Rd, Odenton · verified Oct 11
    See details

    Support local first responders while getting active at a community 5K that welcomes both runners and walkers. Whether you want to push your pace, spend time with family and friends, or take part at your own comfort level, this event invites participants of all abilities. Taking part helps give back to the Odenton community and keeps the focus on fitness and local pride. General registration is $40 per person.

    Event website ↗
  • 4:30pm

    Rick Braun Plays Chuck Mangione

    Rams Head On Stage, 25 West St, Annapolis · verified Oct 9
    See details

    Rick Braun brings a heartfelt salute to Chuck Mangione to Rams Head On Stage, drawing from his first full tribute project devoted to the flugelhorn legend. Inspired by a meaningful meeting years ago at the Long Beach Jazz Festival, where Mangione welcomed him and gifted a Giardinelli flugelhorn mouthpiece, Braun later used that piece throughout the recording as a living connection to his hero. Following Mangione’s passing in 2025, he revisited the music that first moved him at the Eastman School of Music and shaped arrangements that celebrate its joy and warmth. The performance reflects that journey with lyrical flugelhorn on his vintage Couesnon horn and fresh takes on favorites from the tribute, including "Feels So Good," "Land of Make Believe," "Give It All You Got," and selections from Children of Sanchez. This event is open to all ages.

    Event website ↗
Monday, November 16 3 events
  • 6pm

    Monday Night Mysteries: Pinch of Death (11/16)

    Perry's Restaurant, 1210 Annapolis Rd, Odenton · verified Oct 11
    See details

    As part of Monday Night Mysteries at Perry's Restaurant in Odenton, Pinch of Death serves up an interactive, comedic whodunit steeped in culinary intrigue. McGourmet Spice Factory marks its 50th year with its famed Ol' Hon blend, and company chief Sal T. Pepper is set to reveal news that will stir far more than seasonings. What begins as a celebratory gathering soon simmers into secrets, rivalries, and a deadly twist. The price is $74.50 and includes a set menu with multiple choices, the chef’s dessert selection, nonalcoholic beverages, the show, tax, and gratuity. Alcoholic drinks are available for an additional charge. Free on-site parking is provided, there are no ticketing fees, and $74.50 is the final total. Dietary needs can be accommodated with 72 hours notice. Written by Amanda N. Gunther.

    Event website ↗
  • 7:30pm

    Ari Hest - Live at 49 West in Annapolis, MD

    49 West Coffeehouse, Winebar & Gallery, 110 Cathedral St, Annapolis · verified Oct 11
    See details

    Presented by ITZALL GOODE and SHC Music Tribe, Ari Hest performs live at 49 West for an intimate evening of original music. The Grammy-nominated singer and songwriter began as an independent artist, built a devoted college following, and later released Someone To Tell and The Break-In on Columbia Records while touring in the U.S. and overseas with artists including Martin Sexton, Suzanne Vega, and Ani DiFranco. He launched the weekly song series 52, collected favorites on Twelve Mondays, and followed with albums such as Sunset Over Hope Street, The Fire Plays, Shouts And Whispers, and Silver Skies Blue with Judy Collins, which earned a Grammy nomination for Best Folk Album. His songs have appeared on television shows including The Path, The Lincoln Lawyer, Private Practice, Army Wives, and One Tree Hill. He continues to share new music regularly through a song-every-two-weeks series and has gathered fan favorites into The Treehouse Project releases. Tickets are $20 in advance and $25 at the door. Purchasing a ticket serves as your reservation. If you prefer not to buy ahead, call 49 West at (410) 626-9796 to reserve a spot. Please avoid calling to reserve if you have already purchased tickets to prevent duplicate reservations. For questions or more information, email shcmusictribe@gmail.com.

    Event website ↗
  • 8pm

    Lalah Hathaway

    Maryland Hall, 38 Greenfield St, Annapolis · verified Oct 9
    See details

    Five-time Grammy winner Lalah Hathaway takes the stage with the voice and versatility that have defined her career. She is tied with Beyoncé for the most wins in the Best Traditional R&B Performance category, with three each. An artist, singer, songwriter, and producer, she has seven solo albums and an extensive record of collaborations that includes Pharrell Williams, Kendrick Lamar, Dr. Dre, Anderson .Paak, Robert Glasper, Rapsody, Snoop Dogg, and Esperanza Spalding. She has also been invited to perform with Prince, Stevie Wonder, and Herbie Hancock. Born and raised in Chicago and the daughter of the late Donny Hathaway, she brings a rich musical heritage to this performance.

    Event website ↗
Tuesday, November 17 2 events
  • 6pm

    Open Mic Night at Chesepiooc Real Ale Brewery - November 17th

    Chesepiooc Real Ale Brewery, 2408 Crofton Blvd, Crofton
    See details

    Dan and Sara host an open mic night at Chesepiooc Real Ale Brewery. This gathering is family friendly and dog friendly. Beer and nonalcoholic beverages are available, with drink orders taken at the bar. For food, attendees can order in. Vocalists without a guitar are welcome, as Dan keeps a large song library and can often accommodate requests. Sending a message in advance is welcome.

    Event website ↗
  • 7:30pm

    PFLAG Annapolis/AACo Support Meeting

    Unitarian Universalist Church of Annapolis, 333 Dubois Rd, Annapolis
    See details

    This support meeting offers three separate groups for youth, adults, and parents and allies. It takes place at the Unitarian Universalist Church Annapolis in the main church building, not the FAHS House behind the church. The adult group meets on the lower level and can be reached directly from the parking lot through the set of double green doors. The youth group and the parents and allies group meet on the main floor, with entry through the primary entrance.

    Event website ↗
Wednesday, November 18 2 events
  • 5:30pm

    McCoy Solo at Nonna Angela's Italian Bistro & Wine Bar!

    Nonna Angela's Italian Bistro & Wine Bar, 2225 Defense Hwy, Crofton
    See details

    Experience a solo set from McCoy at Nonna Angela's Italian Bistro & Wine Bar. The evening combines dining and live music in one place.

    Event website ↗
  • 8pm

    Deer Tick and more

    Rams Head On Stage, 33 West St, Annapolis · verified Oct 9
    See details

    Deer Tick appears with DUG at Rams Head On Stage for an all ages concert. Deer Tick brings songs from Coin-O-Matic, the band’s ninth album, a self-produced release crafted in their own studio. The record turns toward Rhode Island’s lesser-known stories, where working class life and organized crime intersect, and it traces themes of loss, grit, and hard-won hope. John McCauley, Ian O’Neil, Dennis Ryan, and Christopher Ryan shape cinematic portraits and intimate reflections, joined on select tracks by Steve Berlin on baritone saxophone and former member Rob Crowell on organ for a live-in-the-room energy. The album’s narratives range from quiet to cathartic. Dog Years follows an older man pushed forward by grief. Mary Singletary looks at teenage romance across religious lines with a wink at Catholic guilt. ACI gives voice to someone behind bars, while Exit Door considers the shock of returning to a changed world. O’Neil leads Everything Born, a meditation on love and mortality sparked by new parenthood. Candy Cigarettes ends the journey with a lifelong romance that gently nods to Irish history and the immigrant experience. DUG joins the bill with a transatlantic folk sound. The duo of Conor (Lorkin) O’Reilly and Jonny Pickett formed in 2023 and is preparing a debut album. Their roots stretch across America, Scotland, and Ireland, with O’Reilly’s years in upstate New York informing songs like Big Sundown and Jubilee, the latter shortlisted for two Grammy nominations. Resonator guitar and banjo drive intricate fingerpicking and tight interplay, and their storytelling blends warmth and sly humor, as heard on Wheel of Fortune.

    Event website ↗
Thursday, November 19 1 event
  • 8pm

    DMTB

    Rams Head On Stage, 25 West St, Annapolis · verified Oct 9
    See details

    DMTB honors the music of the Dave Matthews Band, channeling the 90s era of tape trading, big sing-alongs, and adventurous musicianship with intricate guitar work, soaring violin, smooth saxophone, and explorative and explosive drumming. For more than 20 years, this Buffalo, NY based group has toured relentlessly since 2004, performing over 2,000 shows across 46 states and 10 countries, all in service of a heartfelt recreation of DMB’s spirit. With deep respect for the original quintet, the band focuses on the classic sound while also drawing from later and current catalogs to create a balanced, authentic tribute that often makes listeners feel like they have stepped back in time. This event is open to all ages. Tickets are $35 to $45, plus taxes and fees.

    Event website ↗
Friday, November 20 1 event
  • 8pm

    Lonesome River Band

    Rams Head On Stage, 33 West St, Annapolis · verified Oct 9
    See details

    Rams Head On Stage presents Lonesome River Band, a bluegrass quintet more than four decades into its career and led by award-winning banjo player Sammy Shelor. The lineup features Jesse Smathers and Adam Miller on lead vocals alongside Kameron Keller, Mike Hartgrove, and Shelor. Their recent collection, The Winning Hand, showcases both the group’s enduring sound and new ideas, with songs like “Blues of the Night” and “That’s Why Trains Are Lonesome,” country-leaning cuts such as “Near Mrs.” and “She Don’t Know I’m Alive,” and nods to influences including Lost & Found through “Oh, Darlin’” and “Brown Hill.” It also ventures into fresh rhythms on “Charlottesville” and puts fiddle and banjo in the spotlight on Tommy Jackson’s “Tom and Jerry.” The current single, “Queen of Hearts,” highlights Smathers and a co-write with Miller that began with a card game spark. This event is open to all ages.

    Event website ↗
Saturday, November 21 7 events
  • 9:30am

    Meet and Ride

    Chesapeake Cycles, 104 Defense HWY, Annapolis
    See details

    This relaxed group ride takes place on the third Saturday of each month. If weather causes delays, it will be moved to Sunday or to the fourth Saturday or Sunday as needed. Expect an easy, no pressure pace.

    Event website ↗
  • 11am

    Early Thanksgiving Traditions at the Benson-Hammond House

    Benson-Hammond House, 7101 Aviation Blvd, Baltimore · verified Oct 11
    See details

    At the Benson-Hammond House, this friendly program explores how farmers and families in the north county area once celebrated the season, focusing on the foods that filled their tables. Conversation touches on dishes like turnips and sweet potatoes, oyster stuffing, the ham or turkey debate, and even sauerkraut, with pie taking a special place in the mix. Attendees are encouraged to share their own favorite dishes as part of the discussion. The gathering takes place a week early so volunteers can spend the holiday with family.

    Event website ↗
  • 1pm

    Memphis Tigers at Navy Midshipmen Football

    Navy-Marine Corps Memorial Stadium, 550 Taylor Ave, Annapolis
    See details

    At Navy-Marine Corps Memorial Stadium, Memphis and Navy face off in a clash of contrasting philosophies. Memphis leans on a fast-paced attack while Navy relies on a disciplined, run-first approach, creating a contest where clock control, sharp execution, and timely big plays could quickly shift momentum. With meaningful implications late in the season and a setting just outside the Yard, the atmosphere feels distinct compared with the usual weekend slate.

    Event website ↗
  • 6:45pm

    Candlelight: Coldplay & Imagine Dragons

    Maryland Hall, 801 Chase St, Annapolis · verified Oct 11
    See details

    Experience a candlelit tribute to the music of Coldplay and Imagine Dragons at Maryland Hall in Annapolis, presented as an immersive, multi-sensory concert. The Listeso String Quartet performs arrangements of songs including Clocks, Something Just Like This, Radioactive, Adventure of a Lifetime, Fix You, Eyes Closed, Nice to Meet You, The Scientist, feelslikeimfallinginlove, Follow You, Bad Liar, Viva la Vida, Believer, and Sky Full of Stars. This is a tribute performance and is not affiliated with, endorsed by, or sponsored by the artists, their estates, or official representatives. Guests ages 8 and up are welcome, and anyone under 16 must be accompanied by an adult. The venue is ADA compliant. Seating is assigned within each zone as attendees arrive.

    Event website ↗
  • 8pm

    Marshall Crenshaw

    Rams Head On Stage, 25 West St, Annapolis · verified Oct 11
    See details

    Rams Head On Stage presents a performance featuring Marshall Crenshaw with Sarah Borges. Crenshaw’s story starts in Detroit, where he began playing guitar as a child, then moved into the spotlight portraying John Lennon in Beatlemania before settling in New York City. There he formed a rock and roll trio with his brother Robert and bassist Chris Donato, connected with producer Alan Betrock, and released his first single, Something’s Gonna Happen, while Robert Gordon brought wider attention to his songwriting with Someday Someway. Airplay on WNEW-FM boosted his profile, leading to a career spanning four decades, 13 albums, film and television work including portraying Buddy Holly in La Bamba, and thousands of concerts. His current touring band, assembled in 2022, includes multi-instrumentalist and producer Fernando Perdomo, bassist and songwriter Derrick Anderson, and drummer Mark Ortmann, a founding member of the Bottle Rockets. Infocus Visions Music & Arts Magazine described a recent New York show as a high-energy, full-band showcase marked by lively interplay and the signature Marshall Crenshaw sound. This event is open to all ages.

    Event website ↗
  • 8pm

    Perry's Restaurant Odenton

    Perry's Restaurant, 1210 Annapolis Rd, Odenton · verified Oct 11
    See details

    This event features music performed in real time by musicians. It focuses on the immediacy and connection that come with an in-person show.

    Event website ↗
  • 9pm

    Live Music with Mxd

    Blackwall Hitch, 400 6th St, Annapolis · verified Oct 12
    See details

    Settle in for an evening of live music paired with dinner and drinks at Blackwall Hitch Annapolis.

    Event website ↗
Sunday, November 22 5 events
  • 10am

    Soften and Rise Retreat

    553 Choptank Cove Ct, Annapolis · verified Oct 12
    See details

    A one-day retreat in Annapolis offers a gentle pause for those ready to set down what they have been carrying and rise with renewed ease. The day features a circle for community connection, a restorative-style yoga practice, a healing circle focused on breathwork, and sound-centered healing that incorporates acupuncture. A light lunch is included, with additional elements to round out the experience.

    Event website ↗
  • 12pm

    Baubles Bags and Baskets Charity Bingo

    Orchard Beach Volunteer Fire Department, 7549 Solley Rd, Glen Burnie · verified Oct 11
    See details

    Enjoy a lively bingo afternoon at Orchard Beach Volunteer Fire Department in Glen Burnie. Prizes up for grabs include jewelry, designer purses, bags, and gift baskets. There will be raffles, 50/50 boards, a football pool, and more. Admission is $30 per person and includes 20 regular plus door prizes. The Ravens game will be shown live. Food and drinks will be available for purchase, including a beverage wall with a souvenir cup courtesy of BMORE Around Town.

    Event website ↗
  • 3pm

    Breathwork Circle with Trish Brewer at Restore studio

    Restore Studio, 53 Old Solomons Island Rd, Annapolis · verified Oct 11
    See details

    A breathwork circle led by Trish Brewer at Restore studio centers on intentional breathing to support emotional release. Guided exercises use deep, rhythmic breaths that stimulate endorphins, helping participants tap into inner awareness, recalibrate ingrained emotional patterns, and strengthen intuition while opening space for creativity and clear thinking. The gathering offers dedicated time for reflection, deeper breathing, and meaningful connection with others.

    Event website ↗
  • 4:30pm

    Herman's Hermits Starring Peter Noone

    Rams Head On Stage, 25 West St, Annapolis · verified Oct 11
    See details

    Herman’s Hermits starring Peter Noone presents a concert led by the famed vocalist whose career spans stage, screen, and hit records. Known for a lively mix of stories, quick wit, and timeless songs, Noone guides the band through a set filled with music that helped shape a generation. The performance highlights a legacy of more than 60 million records sold and 20 Top 40 singles, delivered with the polish and charm he is known for. This event is open to all ages.

    Event website ↗
  • 7:30pm

    Herman's Hermits Starring Peter Noone

    Rams Head On Stage, 25 West St, Annapolis · verified Oct 11
    See details

    Rams Head On Stage welcomes Herman’s Hermits starring Peter Noone for a concert of classic favorites and lively storytelling. Peter Noone, known for his accomplishments on stage, screen, and in the studio, leads a versatile set filled with songs that helped shape a generation. With over 60 million records sold and 20 songs that reached the Top 40, this all-ages show pairs timeless hits with plenty of playful humor.

    Event website ↗
Tuesday, November 24 1 event
  • 6pm

    Thanksgiving Table Centerpiece

    Willow Oak Flower and Herb Farm, 8109 Telegraph Rd, Severn · verified Oct 11
    See details

    Learn to craft a Thanksgiving table centerpiece featuring a Hurricane-style design with a glass candle surrounded by mums, berries, pods, dried accents, and fresh greenery. This hands-on session is $75 per person. Registration is available by phone at 410-551-2237.

    Event website ↗
Wednesday, November 25 1 event
  • 5:30pm

    Sparks Solo at Nonna Angela's Italian Bistro & Wine Bar

    2225 Defense Hwy, Crofton
    See details

    Sparks presents his monthly solo performance at Nonna Angela's Italian Bistro & Wine Bar, a traditional-style Italian bistro and wine bar.

    Event website ↗
Saturday, November 28 2 events
  • 4:30pm

    North Pole Lights Walk

    Willow Oak Flower & Herb Farm, 8109 Telegraph Rd, Severn · verified Oct 11
    See details

    Set out on a self-guided walk that winds past garden blooms and arctic wildlife on the way to the North Pole Palace. The North Pole Fairy will send you on your way, with a stop to visit Santa in the Garden Cabin and chances to capture photos in his sleigh. New scenes are added each year, and a Christmas barn offers a variety of gifts. The route is about a half mile with many places to pause, and it includes brick, stone, and woodland surfaces. Single strollers and wheelchairs can access the path, though some sections may be more difficult to navigate. Only service dogs are permitted. If weather disrupts plans, tickets can be used on another evening. Tickets are non-refundable but may be moved to a different night. Admission is $12 for adults and $8 for children.

    Event website ↗
  • 8pm

    Nicole Atkins

    Rams Head On Stage, 25 West St, Annapolis
    See details

    Nicole Atkins appears at Rams Head On Stage for an all ages show. Her latest album, Drama, grew out of life on the road and long stretches apart from her tour-manager husband, turning sleepless nights, distance, and uncertainty into songs that reach for connection. On Drama she moves between vintage pop sparkle and modern soul, from the rush of Trippin’ On Teardrops and the Memphis-tinged pulse of For No One to the cinematic shadows of Danny and the big, anthem-ready lift of Singing In The Mirror. Working with producer Patrick Sansone, she threads chamber pop touches through melodies that nod to earlier eras while remaining unmistakably her own. Raised in Neptune City on the Jersey shore, she drew early inspiration from beach-town performers and her family’s record collections, gravitating to bold voices like Candi Staton and Roy Orbison. After the breakthrough of Neptune City in 2007, tours with The Black Keys and Nick Cave, and a period of industry ups and downs, a move to Nashville renewed her focus, with encouragement from Chris Isaak helping pave the way for Drama. Expect an evening centered on expressive storytelling and a powerful voice that embraces big emotion at Rams Head On Stage.

    Event website ↗
Tuesday, December 1 2 events
  • 7pm

    Maryland Hall Presents: The Holidays with Canadian Brass

    Maryland Hall, 38 Greenfield St, Annapolis · verified Oct 11
    See details

    Canadian Brass brings over five decades of holiday cheer with radiant brass harmonies and time honored seasonal classics. A festive program showcases the group’s virtuosity and creates a warm, joyful atmosphere from one of the most acclaimed brass ensembles in the world.

    Event website ↗
  • 7:30pm

    PFLAG Annapolis/AACo Support Meeting

    Unitarian Universalist Church of Annapolis, 333 Dubois Rd, Annapolis
    See details

    This support meeting offers three groups for Youth, Adults, and Parents/Allies. It takes place at the Unitarian Universalist Church Annapolis, not the FAHS House behind the church. The adult group meets on the ground floor and can be accessed directly from the parking lot through the double green doors. The youth and parents/allies groups meet on the main floor and should enter through the main door.

    Event website ↗
Wednesday, December 2 1 event
  • 5:30pm

    Sparks Solo at Nonna Angela's Italian Bistro & Wine Bar

    2225 Defense Hwy, Crofton
    See details

    Sparks performs a bi-monthly solo set at Nonna Angela's Italian Bistro & Wine Bar, a traditional Italian bistro and wine bar. Enjoy live music from Sparks in a solo format at this recurring appearance.

    Event website ↗
Friday, December 4 3 events
  • 9:30am

    Cozy Up to Cuddle® Slippers Class

    The Quilting Parlour, 2110 Priest Bridge Dr, Crofton
    See details

    Learn to sew the Cozy Up to Cuddle Slippers in a hands-on class at The Quilting Parlour in Crofton, Maryland. Cuddle Ambassador Ajaire Parello leads the instruction, sharing professional techniques for working with Shannon Fabrics Cuddle fabrics as participants create a pair of very soft, comfortable slippers. The session focuses on sewing, learning, and creativity in a welcoming setting.

    Event website ↗
  • 1:30pm

    Luxe Cuddle® Milan Blanket Class

    The Quilting Parlour, 2110 Priest Bridge Dr, Crofton
    See details

    Learn to sew the Luxe Cuddle® Milan Blanket in a hands-on class taught by Cuddle® Ambassador Ajaire Parello. Designed for sewists eager to grow their skills, the session guides participants through creating a plush, polished blanket with Cuddle® fabrics. Enjoy a creative and inspiring afternoon at The Quilting Parlour.

    Event website ↗
  • 7pm

    3rd Shift rocks Romilo's

    Romilo's Restaurant, 478 Ritchie Hwy, Severna Park · verified Oct 11
    See details

    A lively night of music awaits in the bar at Romilo’s, with the musicians setting the tone for a fun time. Tables fill quickly, so arrive early if you want a seat. Please remember to tip the bartenders and servers.

    Event website ↗
Saturday, December 5 2 events
  • 11am

    No Place Like the Farm for the Holidays at the Benson-Hammond House

    7101 Aviation Blvd, Baltimore · verified Oct 11
    See details

    This country and farm inspired holiday celebration features cookies along with punch, charming decorations that create a cozy, uplifting atmosphere, and seasonal music performed by the Overtones.

    Event website ↗
  • 3pm

    Grinchmas Family Kids BINGO

    4 Broadview Blvd S, Glen Burnie · verified Oct 11
    Free

    Ferndale VFC presents a Grinchmas themed bingo gathering for kids and their families. Enjoy cheerful bingo play with candy, games, and prizes. Admission is free. To reserve a spot, contact Laura at 443-690-4575 or llong@fvfc34.org. To avoid scams, ignore unsolicited messages requesting money. Official updates will come directly from FVFC.

    Event website ↗
Sunday, December 6 2 events
  • 9am

    Christmas Market!

    45 W Earleigh Heights Rd, Severna Park · verified Oct 11
    See details

    Celebrate the season at a Christmas market with local vendors and holiday cheer. Word on the street is that the big guy will make a special appearance at The Station. Browse offerings from local sellers and enjoy the festive atmosphere.

    Event website ↗
  • 12pm

    No Place Like the Farm for the Holidays at the Benson-Hammond House

    7101 Aviation Blvd, Baltimore · verified Oct 11
    See details

    A farm and country themed holiday celebration at the Benson-Hammond House features holiday decorations throughout, refreshments that include cookies and punch, and holiday music from the Overtones.

    Event website ↗
Wednesday, December 9 3 events
  • 5:30pm

    McCoy Solo at Nonna Angela's Italian Bistro & Wine Bar!

    Nonna Angela's Italian Bistro & Wine Bar, 2225 Defense Hwy, Crofton
    See details

    Spend an evening with Steve as food and music come together.

    Event website ↗
  • 7pm

    Versed Fox Book Club

    35 Maryland Ave, Annapolis
    See details

    A year-end Versed Fox Book Club gathering invites participants to share poems that have stayed with them over the year. Bring a favorite selection or an original piece and take part in an evening that celebrates poetry and shared appreciation.

    Event website ↗
  • 9pm

    Hyland Brothers Live @ Stan & Joe’s

    Stan and Joe's Saloon, 37 West St., Annapolis
    See details

    This event features an in-person musical performance.

    Event website ↗
Friday, December 11 1 event
  • 8:30pm

    Carbon Leaf

    Rams Head On Stage, 25 West St, Annapolis
    See details

    Carbon Leaf brings its folk-infused indie rock to Rams Head On Stage in Annapolis, MD. All ages are welcome. The Richmond, Virginia band’s fifteenth studio album, "Time is the Playground," pairs nostalgic storytelling with layered harmonies, acoustic and electric textures, and reflections on time, love, and growth. Conceived to flow like a start-to-finish story, it balances urgency with calm. The group earned widespread attention with "The Boxer," which won the American Music Awards New Music Award and made them the first unsigned act to perform on the AMAs. Since then they have played more than 3,500 energetic shows, released charting records, and ultimately returned to full independence. They record at guitarist Terry Clark’s Two-Car Studio and release music on their Constant Ivy imprint, even re-recording their Vanguard-era albums to regain the rights. The current lineup includes vocalist Barry Privett, guitarist Terry Clark, multi-instrumentalist Carter Gravatt, bassist Jon Markel, and drummer Jesse Humphrey. New material such as "Backmask 1983" nods to the analog-to-digital crossroads with AC/DC grit and Cars-like synths, peppered with cultural touchstones like Farrah Fawcett, the so-called Satanic Panic, Time Life Books, and Bigfoot. Known for tireless touring and a self-managed approach, the band focuses on songs that listeners can carry with them long after the show.

    Event website ↗
Saturday, December 12 4 events
  • 9:05am

    10th annual Toys For Tots Jack & Jill

    Brews & Cues On The Blvd, 7954 Baltimore Annapolis Boulevard, Glen Burnie · verified Oct 11
    See details

    Now in its tenth year, this Jack and Jill teams tournament takes place at Brews & Cues On The Blvd. Teams enter for $50 and each player brings one new, unwrapped toy. Doors open with on-site check-in and a players meeting before play begins. Matches use BCA 8-ball rules with an alternating break. An 8-ball made on the break is spotted right away and the shooter continues with an open table, and it is not a win or a loss. If the 8 goes in on the break and the breaker scratches, the 8 is spotted and the incoming team receives ball in hand anywhere on the table. Calling a safety while pocketing a ball is allowed. The tournament is double elimination, with races to four on the winner’s side and races to three on the one-loss side.

    Event website ↗
  • 7pm

    LIVE MUSIC with Greg Kneller

    Blackwall Barn & Lodge - Gambrills, 329 Gambrills Rd, Gambrills · verified Oct 11
    See details

    Enjoy dinner and drinks accompanied by live music at The Barn & Lodge.

    Event website ↗
  • 7pm

    Remedy Is Back @ Romilo's. Half-Time Show Brandon Freelump 478 Ritchie Hwy, Severna Park, MD 21146

    Romilo's, 478 Governor Ritchie Hwy, Severna Park · verified Oct 11
    See details

    Remedy opens the new year with its first performance at Romilo's. A fresh start sets the tone for the year ahead.

    Event website ↗
  • 9pm

    One Step Down at Rams Head Tavern in Annapolis, MD

    Rams Head Tavern Annapolis, 33 West St, Annapolis
    See details

    One Step Down brings an acoustic set to the Downbar at Rams Head Tavern in Annapolis, featuring vocalist Karen Leaf and guitarist Joe Puleo. The duo covers a wide range of songs and styles, stretching from Nancy Sinatra to Iron Maiden. It is an evening of live music alongside the tavern's food and drinks.

    Event website ↗
Sunday, December 13 1 event
  • 10am

    Annapolis Striders Anniversary Run 15K 2026

    Quiet Waters Park, Annapolis
    Free

    The Annapolis Striders mark 48 years with a 15K Anniversary Run at Quiet Waters Park. The course features two laps within the park with mild elevation changes, and it serves as the eighth and final event in the 2026 Annapolis Striders Championship Series. Entry is free for club members who register in advance. Non-members pay $15 in advance, and annual memberships cost $30 for individuals and $45 for families, with members receiving complimentary entry. Race day registration is $25 for all participants. Members who registered ahead for the full 2026 Championship Series are already entered and do not need to register again. Volunteer opportunities are available, and questions can be directed to the race director.

    Event website ↗
Monday, December 14 1 event
Tuesday, December 15 1 event
  • 7:30pm

    PFLAG Annapolis/AACo Support Meeting

    Unitarian Universalist Church of Annapolis, 333 Dubois Rd, Annapolis
    See details

    The PFLAG Annapolis/AACo support meeting provides three separate groups for youth, adults, and parents and allies. It takes place at the Unitarian Universalist Church Annapolis, not the FAHS House behind the church. Adults meet on the ground floor, while youth and parents and allies meet on the main floor. For the adult group, enter directly from the parking lot through the double green doors to reach the lower level. For the youth and parents and allies groups, enter through the main door.

    Event website ↗
Wednesday, December 16 1 event
  • 5:30pm

    Sparks Solo at Nonna Angela's Italian Bistro & Wine Bar

    2225 Defense Hwy, Crofton
    See details

    Sparks presents his monthly solo at a traditional style Italian bistro and wine bar.

    Event website ↗
Friday, December 18 1 event
  • 8pm

    Pressing Strings

    Rams Head On Stage, 25 West St, Annapolis
    See details

    Annapolis-bred trio Pressing Strings delivers a vibrant mix of blues grit, folk ease, and modern rock drive, all anchored by heartfelt storytelling and infectious grooves. Frontman Jordan Sokel sings with a smoky warmth and plays intricate guitar lines, while drummer Justin Kruger propels the music with energetic, imaginative rhythms. Bassist Nick Welker adds melodic and chordal depth that makes the three-piece sound rich and full. All three members sing, creating layered harmonies that nod to 1970s Southern California. The set moves from gentle ballads to high-energy numbers, blending introspective lyrics with tight, polished musicianship. The band has toured across the United States, headlined clubs, and appeared at Palisade Roots and Bluegrass Festival, FloydFest, Annapolis Baygrass Music Festival, Firefly, Sweetwater 420Fest, and Cavefest, and has shared the stage with Gov’t Mule, Toad The Wet Sprocket, JJ Grey, and Neil Francis. This performance is open to all ages.

    Event website ↗
Saturday, December 19 2 events
  • 12pm

    Wreath Ceremony

    Annapolis National Cemetery, 800 West St, Annapolis
    Free

    A wreath-laying observance affiliated with Wreaths Across America offers quiet reflection as wreaths are placed in remembrance. The ceremony centers on honoring memories through this meaningful gesture.

    Event website ↗
  • 8pm

    Pressing Strings

    Rams Head On Stage, 25 West St, Annapolis
    See details

    Pressing Strings is a dynamic trio from Annapolis led by guitarist and vocalist Jordan Sokel, known for a fluid mix of blues, rock, and folk that pairs story-driven songs with grooves built to move. Their sound balances bluesy grit, the easy sway of folk, and the punch of modern rock, shifting seamlessly from tender ballads to high energy anthems with thoughtful lyrics and skilled playing. Sokel’s smoky vocals and intricate guitar lines lock in with drummer Justin Kruger’s high-spirited, inventive touch and bassist Nick Welker’s steady, melodic foundation that broadens the group’s full, lush feel. All three members add vocals, layering harmonies that echo the classic Southern California style of the 70s. Together they create an immersive, feel-good sound that connects on both an emotional and musical level. The band has toured across the country, headlined clubs, appeared at festivals including Palisade Roots and Bluegrass Festival, FloydFest, Annapolis Baygrass Music Festival, Firefly, Sweetwater 420Fest, and Cavefest, and shared stages with Gov’t Mule, Toad The Wet Sprocket, JJ Grey, and Neil Francis. Open to all ages.

    Event website ↗
Monday, December 21 1 event
  • 8pm

    Steven Page Formerly of Barenaked Ladies

    Rams Head On Stage, 25 West St, Annapolis
    See details

    Steven Page, formerly of Barenaked Ladies, appears with his Trio for a special concert celebrating his new holiday album, Steven’s Greetings. The set blends fresh originals, festive songs he wrote during his Barenaked Ladies years, and classic seasonal standards, along with selections from a career that spans nearly four decades. This is an all ages show.

    Event website ↗
Tuesday, December 22 1 event
  • 6pm

    Open Mic Night at Chesepiooc Real Ale Brewery - December 22nd

    Chesepiooc Real Ale Brewery, 2408 Crofton Blvd, Crofton
    See details

    Dan and Sara host an open mic night at Chesepiooc Real Ale Brewery in a family friendly setting where dogs are welcome. The bar serves beer and non-alcoholic drinks, and guests are encouraged to place drink orders at the counter to support this local business. Food is not provided, and you can order in. Vocalists who do not have a guitar can still participate. Dan has a large song library and can often accommodate requests, and sending a message in advance is welcome.

    Event website ↗
Wednesday, December 23 1 event
  • 5:30pm

    McCoy Solo at Nonna Angela's Italian Bistro & Wine Bar!

    Nonna Angela's Italian Bistro & Wine Bar, 2225 Defense Hwy, Crofton
    See details

    Spend an evening with Steve enjoying great food and great music.

    Event website ↗
Thursday, December 31 2 events
  • 7pm

    New Years Eve @ Post 40

    500 5th Ave SE, Glen Burnie · verified Oct 11
    See details

    Friends and family are invited to celebrate the arrival of the New Year together.

    Event website ↗
  • 9pm

    Charm City Countdown – New Year’s Eve 2026 at the Hilton BWI Airport Hotel

    Hilton Baltimore BWI Airport, 1739 W Nursery Rd, Linthicum Heights · verified Oct 11
    See details

    Charm City Countdown returns to the Hilton Baltimore BWI Airport with a Wild West Gold Rush Gala that turns the entire hotel into a multiroom New Year’s Eve celebration. Immersive décor, live bands and DJs, premium open bars, and gourmet food stations shape a full-building experience, from lively dance floors to stylish lounges. Multiple themed zones each offer their own soundtrack and atmosphere, leading to a festive midnight countdown with thousands of people celebrating together. The VIP Room serves as the focal point of the night. DJ Infame, The Famous Funk Trio, and The Will Spence Band share the spotlight, blending live musicianship with DJ-driven energy for a distinctive sound unique to this space. Ticket options and VIP upgrades are available for those seeking an elevated experience.

    Event website ↗

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