Events in Annapolis, MD

● Listings verifiedSaturday, September 5 · every listing checked against its source by our Annapolis editors

22This week
85Next 30 days
2Free this week
54Venues tracked
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This weekend in Annapolis

The ones worth planning around. All 6 weekend events →

Live music in Annapolis

3 shows this week.

  • Mon 8pm

    Tuba Skinny

    Rams Head On Stage, 25 West St, Annapolis · verified Aug 30
    See details

    Tuba Skinny brings its rich blend of traditional jazz and American roots music to Rams Head On Stage for an all-ages concert. Over more than a decade, the ensemble has released twelve albums and toured internationally, drawing listeners of every generation with skilled musicianship and a deep catalog. Their sound centers on early jazz while branching into jug band tunes, spirituals, country blues, string band traditions, ragtime, and New Orleans R&B, offering a wide view of Americana through an early 20th century lens. The lineup features cornetist Shaye Cohn, trombonist Barnabus Jones, tubist Todd Burdick, clarinetist Craig Flory, guitarist and vocalist Gregory Sherman, banjoist Max Bien-Kahn, washboard player Robin Rapuzzi, and Erika Lewis on vocals and bass drum. Even as their reputation has grown, the group continues to play in public spaces to connect with audiences from all walks of life, keeping the music lively, open, and full of spontaneity.

    Event website ↗
  • Wed 6:30pm

    Jazz Night

    Reynolds Tavern, 7 Church Cir, Annapolis · verified Sep 4
    See details

    Experience an evening at Reynolds Tavern that pairs dinner with live jazz from the Unified Jazz Ensemble in the 1747 Pub. Cover is $10, and it is waived for guests who choose the fine dining experience. Casual fare is available in the pub. The setting blends dining, music, and the tavern’s history.

    Event website ↗
  • Fri 6:30pm

    2026 Goshen Summer Concert Series

    Goshen Farm, 1420 Cape St Claire Rd, Annapolis · verified Aug 30
    Free

    Enjoy a summer evening at Goshen Farm with a free outdoor concert featuring the 2026 lineup. Set in Cape St. Claire on the Broadneck Peninsula, this family-friendly series spotlights local talent with two bands performing back to back. Seating is limited, so bringing lawn chairs or blankets is recommended. Outside food and drinks are welcome, making it easy to relax with music and spend time with friends. The venue is accessible whether arriving on foot, by bike, or by car.

    Event website ↗

All upcoming events, day by day

Every event we track in Annapolis this week, in order.

Saturday, September 5 3 events
  • 11am

    Visiting Author - L. Ryan Storms, Young Adult Fantasy Adventure

    Page After Page, 1821 Crownsville Rd, Annapolis · verified Aug 30
    See details

    Visiting author L. Ryan Storms, who writes young adult fantasy adventure, will be available for a meet and greet and book signing. Talk with the author about her work and have your books signed.

    Event website ↗
  • 11am

    Visiting Author - Kait Disney-Leugers

    Page After Page, 1797 Crownsville Rd, Annapolis
    See details

    Meet visiting author Kait Disney-Leugers for a relaxed meet and greet focused on paranormal romance, followed by a book signing. Talk with the author about her work and have a book signed. It offers a welcoming opportunity for fans and new readers to connect with her stories.

    Event website ↗
  • 11am

    Visiting Author - Ryan G. Beaty

    Maryland Renaissance Festival, 1797 Crownsville Rd, Annapolis
    See details

    Visiting author Ryan G. Beaty, whose work spans young adult dark fantasy, will be on hand for an author meet and greet and book signing. Guests will have the opportunity to speak with the author about his books and have copies signed.

    Event website ↗
Sunday, September 6 3 events
  • 11am

    Visiting Author - Vista McDowall

    Page After Page, 1797 Crownsville Rd, Annapolis
    See details

    Meet visiting author Vista McDowall for a friendly conversation and signing centered on adult epic fantasy. This event offers a chance to talk with the author about the books, ask questions about the writing, and have copies signed.

    Event website ↗
  • 11am

    Visiting Author - Shana Stephens

    Maryland Renaissance Festival, 1797 Crownsville Rd, Annapolis
    See details

    An author meet and greet with a book signing featuring Shana. Attendees can meet the writer and have books signed.

    Event website ↗
  • 11am

    Annapolis First Sunday Arts Festival

    Calvert and West Streets, Annapolis, MD, United States, Maryland 21401, 63 West St, Annapolis
    Free

    This free admission outdoor art market celebrates local and regional creativity with live music and plentiful dining options. Set within the Annapolis Arts District and the historic district, it offers a lively atmosphere where visitors can browse and buy directly from artisans. Expect a wide range of work, including paintings, photography, wheel-thrown pottery, fused and blown glass, jewelry, woodturned pieces, sculpture, fiber arts, candles, home decor, and more. The festival takes place on the first Sunday of the month from May through November. Parking is available at the Calvert Street Parking Garage and the Whitmore Parking Garage, and Calvert Street will be closed for the festival. Friendly leashed pets are welcome, and caretakers should be mindful that summer pavement can be hot. A full music schedule is available. Presented by the Inner West Street Association.

    Event website ↗
Monday, September 7 3 events
  • 5:30pm

    History Monday

    Annapolis Waterfront Hotel, 80 Compromise St, Annapolis · verified Sep 4
    See details

    History Monday offers a guided tour of the Chesapeake area that takes place while under sail, pairing regional history with the sights along the water. Each week features a specific topic and a guest speaker on board.

    Event website ↗
  • 6:30pm

    Yappy Hour

    Capital SUP, 680 Americana Dr, Annapolis · verified Sep 4
    See details

    Capital SUP hosts a cheerful group paddle where dogs and their people head out on the Chesapeake Bay using stand-up paddleboards or kayaks. Guided by Chan Mee with her pups Kaden and Adalynn, Yappy Hour offers a relaxed time on the water with a friendly, tail-wagging atmosphere. It is a lighthearted Annapolis outing filled with smiles and quality time alongside a four-legged companion.

    Event website ↗
  • 8pm

    Tuba Skinny

    Rams Head On Stage, 25 West St, Annapolis · verified Aug 30
    See details

    Tuba Skinny brings its rich blend of traditional jazz and American roots music to Rams Head On Stage for an all-ages concert. Over more than a decade, the ensemble has released twelve albums and toured internationally, drawing listeners of every generation with skilled musicianship and a deep catalog. Their sound centers on early jazz while branching into jug band tunes, spirituals, country blues, string band traditions, ragtime, and New Orleans R&B, offering a wide view of Americana through an early 20th century lens. The lineup features cornetist Shaye Cohn, trombonist Barnabus Jones, tubist Todd Burdick, clarinetist Craig Flory, guitarist and vocalist Gregory Sherman, banjoist Max Bien-Kahn, washboard player Robin Rapuzzi, and Erika Lewis on vocals and bass drum. Even as their reputation has grown, the group continues to play in public spaces to connect with audiences from all walks of life, keeping the music lively, open, and full of spontaneity.

    Event website ↗
Tuesday, September 8 3 events
  • 5:30pm

    Beer Tasting Sunset Sail

    80 Compromise St, Annapolis · verified Aug 30
    See details

    Take to the water for a guided beer tasting while under sail. Each month highlights a different Chesapeake area brewery, with a brewery representative on board to share insights about beer. Sample three beers during the sail, then purchase full beers from the ones you liked best. A schedule of featured breweries is available.

    Event website ↗
  • 7pm

    Citizens & Sovereigns Book Club

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

    Citizens & Sovereigns Book Club presents a discussion of Persepolis 2 by Marjane Satrapi, a graphic memoir that follows her journey to adulthood across revolutionary Iran and Europe. The conversation explores belonging and personal freedom alongside the demands of family, culture, and society depicted in the story. It also highlights resilience and the search for identity amid a changing world.

    Event website ↗
  • 7pm

    Charm City Trivia

    GameOn bar+arcade, 114 West St, Annapolis · verified Aug 31
    See details

    Charm City Trivia is a trivia night with a friendly crowd, tasty food, and plenty of laughter.

    Event website ↗
Wednesday, September 9 3 events
  • 6:30pm

    Jazz Night

    Reynolds Tavern, 7 Church Cir, Annapolis · verified Sep 4
    See details

    Experience an evening at Reynolds Tavern that pairs dinner with live jazz from the Unified Jazz Ensemble in the 1747 Pub. Cover is $10, and it is waived for guests who choose the fine dining experience. Casual fare is available in the pub. The setting blends dining, music, and the tavern’s history.

    Event website ↗
  • 7pm

    Versed Fox Book Club

    35 Maryland Ave, Annapolis · verified Aug 30
    See details

    Versed Fox Book Club turns to the poetry of Omar Khayyám, the writer renowned for The Rubáiyát, where he weaves philosophical reflection, a skeptical streak, and an appreciation for life’s brief joys. The reading showcases lyrical, meditative verses that invite thoughtful consideration of time, destiny, and the deeper mysteries of existence.

    Event website ↗
  • 7pm

    yoga for every trimester: prenatal yoga series

    48 Maryland Ave, Annapolis · verified Aug 30
    See details

    Designed for every stage of pregnancy, this six-week prenatal yoga series offers gentle movement and breathwork in a supportive group setting. Guided by Erin Carlson, RPYT, LMT, and certified doula, each class focuses on building strength, stability, and a deeper mind-body connection. Brief prenatal education is included, and there is time for questions throughout. Participants can enroll for the entire series or attend individual sessions, since each class stands on its own.

    Event website ↗
Thursday, September 10 3 events
  • 7am

    2026 Maryland State GPA Championship & Tribute to 9/11 First Responders Match

    Anne Arundel Fish & Game Conservation Association, 1730 St Margarets Rd, Annapolis · verified Aug 30
    See details

    This GPA sanctioned event brings together ten stages totaling 250 rounds. All proceeds will be directed to charities that support first responders.

    Event website ↗
  • 6:30pm

    Creative Circle - Monthly Meetup (2026)

    111 Chinquapin Round Rd, Annapolis
    See details

    A monthly meetup that invites creatives to explore new materials, spark ideas, and connect with like-minded people. Attend as a drop in for a single session or take part in the full five session series. No prior experience is required, just curiosity and a willingness to experiment. Each gathering introduces a fresh medium and a new challenge, led by Creative Kate, an art coach who opens with an optional warm up to shake off the week, a surprise material to kick start imagination, a prompt to dive into, suggestions for continuing the work at home, and a step by step approach that lets you choose how much guidance you want. Previous sessions have played with mystery boxes, black and white pieces using ink with salt and pepper, bedazzled resin jewelry with a futuristic twist, circular weaving, tiny clay foods, and more. This term includes hands on play with pop up art, iron on wall fabric, mosaics, upcycling, and take home prompts to keep the momentum going. Participants can also bring their own projects to stay accountable to personal goals. All art forms are welcome, though oil or spray paints are not permitted. Expect access to a range of supplies in the studio, idea sharing and feedback from peers, and support for moving past creative blocks like the blank page. Past attendees describe the atmosphere as calm, kind, encouraging, and low pressure. Because class sizes are small, refunds are not available for missed sessions. If there is a waitlist and the spot can be filled, a refund may be issued. Masks are optional for indoor classes and events, and the mask policy may change with advance notice.

    Event website ↗
  • 7pm

    Crystal Ashram Monthly Meditation in Annapolis

    Annapolis Friends Meeting, 351 Dubois Rd, Annapolis
    See details

    Experience a monthly community meditation in Annapolis centered on a restorative sound bath at Annapolis Friends Meeting, Quakers. A sound frequency specialist guides the session with Tibetan singing bowls, including rare, multi-metal instruments with some dating back more than two centuries. The practice is non-religious and weaves historical roots with contemporary perspectives on sound and well-being. Each gathering offers something new, from chakra-focused meditations and gong baths to themed experiences that celebrate the natural world. First-timers are welcome. Bring a yoga mat, blanket, or pillow and settle in however you are most comfortable, whether lying down, seated, or standing. Please arrive before the meditation begins, as late entry is not permitted once it starts. A quiet conversation follows the session. A sliding-scale contribution of $20 to $40 is suggested, with proceeds benefiting the Crystal Ashram 501(c)(3) nonprofit.

    Event website ↗
Friday, September 11 4 events
  • 9am

    Providence Fall Plant & Pottery Sale

    Providence Greenhouses, 370 Shore Acres Rd, Arnold · verified Sep 4
    See details

    This seasonal sale at Providence Greenhouses features a beautiful selection of fall mums and asters, fall perennials, and other bedding plants to brighten home and garden spaces. Shoppers can also find unique seasonal pottery and handmade gifts suited for fall decorating, hosting, and gift giving. The sale is rain or shine, and credit cards are accepted.

    Event website ↗
  • 5pm

    2026 Maryland Seafood Festival

    Sandy Point State Park East Beach
    See details

    The 58th Maryland Seafood Festival marks six decades since its start in 1966, celebrating seafood, family activities, and the Chesapeake Bay. At Sandy Point State Park East Beach, attendees can enjoy live music, chef demonstrations, a wide range of seafood, artisan craft booths, and a hands-on area for children. Skipjack Heritage Days returns as part of the festivities.

    Event website ↗
  • 6:30pm

    2026 Goshen Summer Concert Series

    Goshen Farm, 1420 Cape St Claire Rd, Annapolis · verified Aug 30
    Free

    Enjoy a summer evening at Goshen Farm with a free outdoor concert featuring the 2026 lineup. Set in Cape St. Claire on the Broadneck Peninsula, this family-friendly series spotlights local talent with two bands performing back to back. Seating is limited, so bringing lawn chairs or blankets is recommended. Outside food and drinks are welcome, making it easy to relax with music and spend time with friends. The venue is accessible whether arriving on foot, by bike, or by car.

    Event website ↗
  • 8pm

    Our Town by Thornton Wilder

    The Colonial Players, 108 East St, Annapolis · verified Sep 4
    See details

    Thornton Wilder’s Our Town arrives under the direction of Rick Wade, tracing the everyday lives of two families in a small town. The story gently asks whether we recognize the value of our days as we live them. It offers a moving portrait of friendship, family, love, and the ties that bind a community. Content advisory: depictions of death and loss, with themes of grief and existential reflection.

    Event website ↗

All upcoming events127 more events through Nov 22

Everything else on Annapolis's calendar over the next 30 days, in order.

Saturday, September 12 9 events
  • 9am

    Providence Fall Plant & Pottery Sale

    Providence Greenhouses, 370 Shore Acres Rd, Arnold · verified Sep 4
    See details

    Shop a seasonal selection of fall mums, asters, fall perennials, and bedding plants to refresh your home and garden. Browse unique pottery and handmade gifts suited for fall decorating, hosting, and gift giving. The sale takes place at Providence Greenhouses, runs rain or shine, and accepts credit cards.

    Event website ↗
  • 9am

    Sup Yoga with Allie

    Capital SUP, 655 Americana Dr, Annapolis · verified Sep 4
    See details

    Experience stand-up paddleboard yoga on the calm waters at Capital SUP. The class weaves an energizing vinyasa flow with soothing, longer stretches for a balanced practice. It begins with breath-centered sequences that build strength and stability, then transitions into relaxing holds to release tension and settle the mind. Suitable for all levels, including anyone new to yoga, paddleboarding, or both. Expect mindful breathing, intentional movement, and a serene setting on the water.

    Event website ↗
  • 10am

    Chaste Treasure at the Maryland Renaissance Festival

    Maryland Renaissance Festival
    See details

    Chaste Treasure returns to Revel Grove for three weekends of fun at the Maryland Renaissance Festival.

    Event website ↗
  • 11am

    Visiting Author - Angela Mitchell

    Maryland Renaissance Festival, 1797 Crownsville Rd, Annapolis · verified Aug 30
    See details

    Meet the author in person and get books signed, with a special focus on The Chesapeake Mermaid. The event centers on informal conversation and autograph opportunities.

    Event website ↗
  • 11am

    Visiting Authors

    Maryland Renaissance Festival, 1821 Crownsville Rd, Annapolis · verified Aug 30
    See details

    Creators from Unicycle Games will be on hand for a friendly meet and greet and a book signing. Chat with the author and illustrator about their work and have a book signed.

    Event website ↗
  • 11am

    2026 Drug Education & Awareness Sporting Festival

    Annapolis Recreation & Parks, 273 Hilltop Ln, Annapolis · verified Aug 30
    Free

    Drug Free All Stars is hosting a community sporting festival at Annapolis Recreation & Parks, Griscom 1, focused on drug education and awareness. The day features free soccer and basketball clinics, a moon bounce, an obstacle course, and free food. Youth attendees can receive a T-shirt and a swag bag. A kickball matchup will see Drug Free All Stars face One Annapolis. Educational groups and vendors will share prevention information and useful resources, creating a family friendly atmosphere with plenty of activities.

    Event website ↗
  • 11am

    Visiting Author - Theresa Biehle, Teen Epic Fantasy

    Maryland Renaissance Festival, 1821 Crownsville Rd, Annapolis · verified Sep 4
    See details

    Meet visiting author Theresa Biehle at an author meet-and-greet and book signing focused on teen epic fantasy. Learn more about her books and have books signed.

    Event website ↗
  • 5pm

    Annapolis RISE Flag Football 2026 Fall Season

    Annapolis High School, 2700 Riva Rd, Annapolis · verified Sep 4
    See details

    Registration is open for the Annapolis RISE flag football fall season, with all games played on the turf fields at Annapolis High School. The format is 6-on-6, with divisions for boys and girls in kindergarten through eighth grade, plus a dedicated girls high school division for grades nine through twelve. Teams can expect six to eight games, including playoffs. The program has supported local families across 22 seasons since 2015. A $30 registration savings is available.

    Event website ↗
  • 8pm

    Maggie Rose and more

    Rams Head On Stage, 25 West St, Annapolis · verified Sep 4
    See details

    Maggie Rose Band takes the stage at Rams Head On Stage with Twinnie for an all-ages performance. The Nashville singer and songwriter arrives with growing acclaim, including consecutive GRAMMY nominations for the album No One Gets Out Alive and the single Poison In My Well, plus recognition from the Americana Music Association as Emerging Act of the Year. Her latest album, Half Moon, captures a moment of artistic expansion, weaving soulful symphonic pop, R&B, and Americana. Created with producers Lawrence Rothman and Daniel Tashian, the music began in relaxed writing sessions surrounded by an array of instruments, then came to life at RCA Studio A with a large ensemble that included her touring band and notable players such as Tom Bukovac, Dennis Crouch, and Peter Levin. The sound embraces lush strings and warm horns for a sweeping feel that steps beyond the rootsy soul of her previous record. Songs like Used To It, Red Shoes, The Mission, Gentle Man, and Hiding In Plain Sight reflect the album’s range, from dance-ready energy to intimate reflection. Expect commanding vocals and richly textured arrangements, with Twinnie adding to the lineup.

    Event website ↗
Sunday, September 13 7 events
  • 7am

    2026 Bay Bridge Paddle

    Sandy Point State Park, 1100 E College Pkwy, Annapolis
    See details

    The tenth annual Bay Bridge Paddle takes place on the Chesapeake Bay’s warm waters and features race courses for every skill level, from beginners to advanced paddlers. It is designed to welcome those just getting started as well as challenge experienced racers. The event also supports nonprofit and charitable partners.

    Event website ↗
  • 10am

    Yoga On The Point

    Ferry Point Marina, 700 Mill Creek Rd, Arnold · verified Sep 4
    See details

    An all-levels Vinyasa session unfolds on the waterfront at Ferry Point Marina as part of the Yoga On the Point summer series. Yoga Barn teachers lead the flow with the Magothy River as a scenic backdrop, creating a calm setting for movement and breath. After class, enjoy a sparkling water at the picnic tables or visit The Point Crabhouse for a meal. Participants may also bring a personal paddlecraft to launch from the marina for a small fee before or after class. Book with a Yoga Barn class pack or choose a drop-in for $28.

    Event website ↗
  • 11am

    Visiting Author - Hannah Levin

    Maryland Renaissance Festival, 1821 Crownsville Rd, Annapolis · verified Sep 4
    See details

    Visiting author Hannah Levin will be on hand for a meet and greet and book signing. Featuring her portal romantasy, this event offers readers a friendly chance to say hello, talk about her books, and get signatures.

    Event website ↗
  • 11am

    Visiting Author - Golden Angel

    Page After Page, 1797 Crownsville Rd, Annapolis · verified Sep 4
    See details

    This event features an author meet and greet and a book signing, along with an opportunity to learn more about Angel’s books.

    Event website ↗
  • 1pm

    Anchored in Hope: An End of Summer Soirée

    The Atreeum at Soaring Timbers, 610 North Bestgate Road, Annapolis · verified Aug 30
    See details

    An elegant end of summer gathering that benefits Archie’s Anchors, featuring live music, coastal flavors, and an open bar in Annapolis. The afternoon supports efforts to foster hope, broaden awareness, and further research for AHC.

    Event website ↗
  • 2pm

    Oktoberfest

    Old Stein Inn, 1145 Mayo Rd, Edgewater · verified Sep 4
    See details

    An Oktoberfest celebration takes place in the Biergarten, featuring a performance by The Polka Terps Band.

    Event website ↗
  • 8pm

    Josiah and the Bonnevilles

    Rams Head On Stage, 25 West St, Annapolis · verified Sep 4
    See details

    Rams Head On Stage welcomes a solo evening with Josiah and the Bonnevilles, the banner for singer songwriter Josiah Leming. Known for raw emotion and a close connection with his audience, he brings a road-honed perspective shaped by East Tennessee roots, early major label experience, and a determined indie journey supported by the fan community he calls the Bonnevilles. Following a year that included a sold out 33 date headlining run and international stops, his tenth studio album, As Is, widens the palette with more electric textures while stepping back from the online noise. The record focuses on joy, sorrow, and working class realities, and features co-writes with Natalie Hemby, Joel Little, Scott Harris and others, with Konrad Snyder as co-producer. On stage he is recognized for vivid storytelling, precise yet heartfelt lyrics, and vulnerable vocals that create an immediate bond in the room. All ages are welcome.

    Event website ↗
Monday, September 14 1 event
  • 5:30pm

    Mediumship Experience and Dinner

    Luna Blu Ristorante, 36 West St, Annapolis · verified Sep 4
    See details

    Experience an evening of mediumship and dining at Luna Blu Ristorante in Annapolis with Medium Debbie. The night begins with a chef-prepared plated dinner, then Debbie offers messages from Spirit to selected audience members. Not every guest will receive a personal reading, yet everyone can observe the process and learn more about mediumship. Tickets are $95 per person, which includes the event and dinner with tax and gratuity included. A cash bar will be available. Attendees must be 18 years of age or older.

    Event website ↗
Tuesday, September 15 3 events
  • 10am

    Tots@10:00

    Annapolis Town Center, 307 Sail Pl, Annapolis · verified Aug 30
    See details

    Annapolis Town Center hosts a monthly program created for families with preschool-aged children, featuring a new theme each month and activities led by local business partners. The theme for this edition is Keep on Truckin’, offering a construction-focused morning with a variety of trucks and vehicles for kids to explore. The event is sponsored by Crab Kickers. After the activities, families can stay for lunch and take advantage of kids eat free offers at participating eateries with the purchase of an adult meal. Augie’s Mussel House provides a complimentary kids meal with an adult main course. Neo Pizza includes a kids meal with a side and beverage when an adult meal is purchased for children 12 and under. P. F. Chang’s offers a free kids meal with an adult lunch purchase. Toastique includes a free house made treat with the purchase of a large smoothie or an item of similar value. True Food Kitchen provides a free kids meal with a purchase of 25 dollars or more for dine in only, with the 25 dollar minimum not counting the kids meal. Giolitti Delicatessen offers a complimentary kid size Italian mac and cheese for dine in only with no substitutions.

    Event website ↗
  • 7pm

    Bluegrass Jam

    Coconut Joe's Bar & Grill, 40 South River Rd, Edgewater
    See details

    Bluegrass fills Coconut Joe's Bar & Grill with an Annapolis jam centered on community and song. Covered space supports up to three jam circles, and porches, lawns, and docks offer additional spots to play and listen. Expect pickers trading tunes, smiles all around, and a setting that highlights gratitude, friendship, and great music. Open to listeners, pickers, and the broader bluegrass family, with plenty of chances to pick, sing, and make music by the bay.

    Event website ↗
  • 7:30pm

    PFLAG Annapolis/AACo Support Meeting

    Unitarian Universalist Church of Annapolis, 333 Dubois Rd, Annapolis · verified Sep 4
    See details

    Three concurrent support groups welcome participants with spaces for youth, adults, and parents or allies. The gathering takes place at the Unitarian Universalist Church of Annapolis, not the FAHS House behind the church. The adult group meets on the ground floor and is accessible from the parking lot through the double green doors. Youth and the parents or allies group meet on the main floor and should use the building’s primary entrance.

    Event website ↗
Wednesday, September 16 1 event
  • 8pm

    The Robert Cray Band

    Rams Head On Stage, 25 West St, Annapolis · verified Sep 4
    See details

    The Robert Cray Band brings the All Amped Up Tour to Rams Head On Stage. Since 1974, the group has forged a signature blend of soul, R&B, gospel, blues, and rock and roll, earning five Grammy Awards, induction into the Blues Hall of Fame, and the Americana Music Awards Lifetime Achievement for Performance. Across more than twenty acclaimed albums and millions of sales worldwide, Robert Cray has collaborated with and shared major stages alongside Albert Collins, Muddy Waters, John Lee Hooker, The Rolling Stones, Tina Turner, and Eric Clapton. Producer Steve Jordan has praised Cray’s distinctive guitar work and standout vocals, and the band continues to perform with enduring enthusiasm and joy. This is an all ages show.

    Event website ↗
Thursday, September 17 3 events
  • 10am

    2026 J30 North American Championship

    Eastport Yacht Club, 317 1st St, Annapolis
    See details

    Annapolis welcomes J/30 sailors for the 2026 North American Championship hosted by Eastport Yacht Club, bringing top one design racing to the Chesapeake. Across three days, racers can expect close competition, waterfront camaraderie, and the club’s hallmark hospitality. The season often brings steady breeze and beautiful conditions, ideal for testing skills, reconnecting with fleet friends, and enjoying everything Annapolis offers. Running alongside the Cal 25 North Americans, the regatta features separate starts for each class while sharing the racecourse, dockside conversations, and post race gatherings, creating a lively, competitive, community driven experience. Registration is open.

    Event website ↗
  • 6pm

    The Art Bar

    AND Creative Gallery, 1851 McGuckian St, Annapolis · verified Sep 4
    See details

    The studio glows with candlelight, creating a cozy, lounge-like setting. A friendly server visits each table with a menu of creative options so participants can choose a project that suits them. The session provides two hours to craft something beautiful while connecting with others. Options include watercolor on paper, friendship bracelets, collage, charcoal with oil pastels, and air dry clay or Model Magic.

    Event website ↗
  • 8pm

    Here Come the Mummies

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

    Here Come the Mummies bring an eight-piece funk rock spectacle to Rams Head On Stage, with mummy-clad performers, tight grooves, and a playful, spooky flair. The band has supported acts such as P-Funk, Al Green, Mavis Staples, KC and the Sunshine Band, and Cheap Trick, performed at Super Bowl Village, become regulars on The Bob and Tom Show, appeared on That’s My Jam with Jimmy Fallon, and taken the stage at major festivals including Summerfest, Summer Camp, Bluesfest Byron Bay, Musikfest, and Suwannee Hulaween. Expect a high-energy set and a larger-than-life persona that have helped them sell thousands of tickets across North America. This show is open to all ages.

    Event website ↗
Saturday, September 19 4 events
  • 10am

    Baygrass 2026

    Sandy Point State Park, 1100 E College Pkwy, Annapolis
    See details

    Set along the beach at Sandy Point State Park in Annapolis, Maryland, this Baygrass celebration brings bluegrass, jamgrass, Americana, and more to neighboring stages by the water. The lineup features Little Feat, Yonder Mountain String Band, Béla Fleck My Bluegrass Heart, Sam Bush, Mountain Grass Unit, TopHouse, Shadowgrass, SCYTHIAN, Sister Sadie, Fireside Collective, Midnight North, Jammy Buffet, Melody Trucks & The Fitzkee Brothers Band, and Geraldine. Artists-at-large Allie Kral on fiddle, Uncle 'Al' Lee on pedal steel, and Patrick Rainey on sax will appear for special collaborations. In addition to the music, attendees can expect locally sourced food that includes fresh oysters, regional microbrews, craft cocktails and wines, a lively beer garden, beach yoga, beach and yard games, activities for kids, local craft vendors, music and Bay conservation workshops, and an elevated VIP experience. The festival centers a mission of caring for the Chesapeake Bay through education, awareness, and donations from festival sales, while also promoting mental wellness by connecting the community with helpful resources.

    Event website ↗
  • 4pm

    21st Annual Boatyard Beach Bash

    Annapolis Maritime Museum, 723 2nd St, Annapolis
    See details

    The 21st Annual Boatyard Beach Bash at the Annapolis Maritime Museum & Park’s Museum Campus honors the legacy of Jimmy Buffett with a Key West inspired celebration featuring members of his Coral Reefer Band. John Frinzi appears with Doyle Grisham, Nadirah Shakoor, and John Patti for a set of Jimmy Buffett classics. The Floating Collective Band includes Coral Reefer legacy artists Mick Utley, Brendan Mayer, and Erin McAnally. Scott Kirby brings island themed songwriting and storytelling, and the Peter Mayer Band features Peter Mayer with Brendan Mayer, Zeb Briskovich, and Miles Vandiver. Radio Margaritaville’s JD Spradlin emcees the show. Tickets are $150.

    Event website ↗
  • 4:30pm

    Peter Mayer Group

    Annapolis Maritime Museum & Park, 723 2nd St, Annapolis
    See details

    At the Annapolis Maritime Museum & Park, the 21st Annual Boatyard Beach Bash honors the memory of Jimmy Buffett with a Key West inspired celebration led by artists connected to his Coral Reefer Band. John Frinzi appears with Coral Reefer members Doyle Grisham and Nadirah Shakoor, joined by John Patti, for an extensive set of Jimmy Buffett classics. The Floating Collective Band features Coral Reefer legacy performers Mick Utley, Brendan Mayer, and Erin McAnally. The Scott Kirby Trio brings coastal storytelling, rich harmonies, and an easygoing island sound. Peter Mayer leads his band with Brendan Mayer, Zeb Briskovich, and Miles Vandiver. Radio Margaritaville’s JD Spradlin serves as emcee.

    Event website ↗
  • 8pm

    Sam Grisman Project

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

    At Rams Head On Stage, the Sam Grisman Project offers an immersive acoustic experience guided by bassist and bandleader Sam Grisman, drawing on the acoustic lineage connected to Jerry Garcia and David Grisman. Raised in Mill Valley in a household where his father, mandolinist, composer, and producer David Grisman, regularly recorded with friends, Sam grew up hearing artists like Doc Watson, Jerry Garcia, John Hartford, Mike Seeger, and Tony Rice, influences that shaped his musical path. The group performs in a spirit of shared reverence between stage and audience, celebrating the music and musicians who continue to inspire them. The ensemble functions as a fluid collective, with a rotating roster that has featured guitarists Max Flansburg, Logan Ledger, Sam Leslie, Henry Moser, Jesse Harper, and Jefferson Hamer, mandolinists Dominick Leslie, Joe K. Walsh, Matt Flinner, and Jesse Appelman, clawhammer banjo player Victor Furtado, fiddlers John Mailander, Alex Hargreaves, Nate Leath, Shad Cobb, and Phoebe Hunt, cellist Nat Smith, and Dobro player Todd Livingston. The project often collaborates with Peter Rowan, and over time has welcomed guests such as David Grisman, John Sebastian, Tim O’Brien, Billy Strings, Maria Muldaur, and Margo Price. Performances are fully acoustic, with instruments and voices captured by condenser microphones to preserve their natural character. Because the sound is sensitive, conversation is best saved for before and after the music or during the set break. This event is open to all ages.

    Event website ↗
Sunday, September 20 5 events
  • 11am

    Visiting Author - Jamie L.H. Goodall, Pirate History

    Maryland Renaissance Festival, 1797 Crownsville Rd, Annapolis
    See details

    Visiting author Jamie L.H. Goodall presents an event focused on pirate history. It features a meet and greet with the author and a book signing.

    Event website ↗
  • 11am

    Visiting Author - Lillie Lainoff, Historical Adventure

    Page After Page, 1821 Crownsville Rd, Annapolis
    See details

    Meet visiting author Lillie Lainoff during a meet and greet and book signing centered on historical adventure. Attendees can have a copy signed by the author.

    Event website ↗
  • 11am

    Anchors & Artisans

    Annapolis Town Center, 1905 Towne Centre Blvd, Annapolis
    See details

    Back for a second year after a popular debut, this artisan and maker market fills Annapolis Town Center with local creativity and community spirit. Browse more than 50 vendors featuring handmade goods while local bands play live music. Take part in themed craft activities for kids and adults, plus other interactive fun such as face painting. Eateries throughout the shopping center offer plenty of food options. Bring a blanket to relax on the turf, enjoy a picnic, and spend time outdoors. The market pops up along the road near Free People and South Moon Under within the center. Admission is free, and parking is complimentary in the shopping center garages. All ages are welcome, with children accompanied by a parent or supervising adult. Dogs are welcome in the outdoor common areas at the event, and individual stores may have their own policies for non-service pets.

    Event website ↗
  • 11am

    Visiting Author - V.L. Valentine, Historical Fiction

    Page After Page, 1797 Crownsville Rd, Annapolis · verified Aug 30
    See details

    Meet visiting author V.L. Valentine for a friendly meet and greet centered on historical fiction. Chat with the writer and get books signed. This casual gathering offers a chance to connect with the author and learn more about their work.

    Event website ↗
  • 8pm

    Cyril Neville

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

    At Rams Head On Stage, Cyril Neville presents Cyril Neville Plays The Dead, showcasing the Uptown Ruler in a fresh creative chapter filled with new music and a forward-looking spirit. A two-time Grammy winner and a cornerstone of New Orleans funky soul, rock and jazz, Neville has spent decades performing worldwide as a vocalist, songwriter, percussionist, painter, cultural figure and activist. He helped define the sound of The Meters and later the Neville Brothers, earned a Grammy for Healing Chant, and The Meters were honored with a Grammy Lifetime Achievement Award. His collaborations span Bob Dylan, Dr. John, Willie Nelson, Carlos Santana, Jimmy Buffett and Branford Marsalis, and he has co-written with Bono, Allen Toussaint, Trombone Shorty and Taj Mahal. Audiences may also recognize him from appearances on Saturday Night Live, NCIS: New Orleans and HBO’s Treme. This event is open to all ages.

    Event website ↗
Monday, September 21 1 event
  • 7:30pm

    MUTLU

    49 West Coffeehouse, Winebar & Gallery, 49 West St, Annapolis
    See details

    ITZALL Goode and SHC Music present an evening at 49 West featuring Mutlu with special guest Noah Pierre. Expect soulful, folk-rooted songwriting with touches of R&B and Americana. Mutlu, a Philadelphia artist steeped in the city’s soul tradition, built his career from local clubs to national and international tours. He first hit the road opening for Joe Jackson, then crossed the U.S. and Europe with Amos Lee and later supported Daryl Hall & John Oates on a theater tour. His releases range from the Manhattan Records album Livin’ It to independent projects including Good Trouble, alongside multiple appearances on Live From Daryl’s House. He is known for a smooth, emotive voice that unites influences from soul, reggae, world music, and folk. DMV-based songwriter Noah Pierre brings an intimate, acoustic set that puts the spotlight on strong songs, clear vocals, and unfussy arrangements, well suited to listening rooms and songwriter-focused spaces. Tickets are $20 online and $25 at the door. Buying in advance serves as your reservation, so there is no need to call the venue.

    Event website ↗
Tuesday, September 22 1 event
  • 7pm

    We Flourish Monthly Gathering

    Toast the 21st, 1355 Generals Hwy, Crownsville · verified Sep 4
    See details

    At Toast the 21st, the WE Flourish monthly gathering brings people together to honor sisterhood through games and playful activities. It creates space to get acquainted in a relaxed setting and enjoy time together.

    Event website ↗
Wednesday, September 23 2 events
  • 7pm

    "Painting the Town" An Urban Watercolor Painting Experience

    Fleet Street, 28 Fleet St, Annapolis · verified Sep 4
    See details

    Artist Em Campbell leads a 90 minute outdoor watercolor workshop in the heart of Old Town Annapolis. Designed for beginners and experienced painters alike, this small group experience builds confidence painting on location and keeps the focus on clarity and ease. Participants explore how to select a subject, simplify complex scenes, and convey a sense of place without getting bogged down in detail. Instruction covers practical outdoor techniques such as setting up efficiently, composing strong layouts, working with a limited palette, and adapting to changing light. Everyone completes a small urban landscape painting and leaves ready to continue painting independently. A professional grade travel watercolor kit is available to purchase during registration. Space is limited for a more personal experience. This class takes place outside, so dress for the weather and consider bringing a chair or cushion for comfort.

    Event website ↗
  • 8pm

    Sean Hayes

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

    Sean Hayes appears at Rams Head On Stage with Etienne de Rocher (Haunted Shed). The San Francisco Bay Area singer-songwriter is known for a gritty mix of folk, soul, and roots influenced by R&B, pairing a gravelly, soulful voice with intimate storytelling and rhythms that invite movement. He has collaborated and toured with Aimee Mann, Frazey Ford, Charley Crockett, Jolie Holland, The Wood Brothers, Ani DiFranco, and The Cold War Kids, with remixes by house DJ Mark Farina and features on NPR, NBC, and HBO. Hayes performs in solo settings as well as with a full band. This event is open to all ages.

    Event website ↗
Thursday, September 24 1 event
  • 8pm

    Brett Dennen

    Rams Head On Stage, 25 West St, Annapolis
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    Brett Dennen brings Art Is Life to the stage with the reflective songwriting that has defined his career. The California singer songwriter recently released his eighth solo album, If It Takes Forever, a collection shaped by a year of notes, voice memos, and quiet reflection after the loss of his father. Recorded quickly with his live band and producer Jon Solo, the music pairs intimate lyrics and warm acoustic textures with touches of dusky Americana, harmonica-driven blues, rootsy indie, and contemplative folk rock. Songs such as In the Garden, Wood Canoe, Another Day in Babylon, Chipping Away, Dharma Baby, and Star Surfer explore love, resilience, and the search for meaning through vivid imagery and layered arrangements. Since his 2004 debut, Dennen has built a devoted following through steady touring with artists like John Mayer, Jason Mraz, and G Love and Special Sauce, plus notable TV placements including Parenthood and the theme for About A Boy, and he has earned multiple AAA radio top 10s, with See the World reaching No. 4 in 2021. This event is open to all ages, and it centers on the idea that art can transform life’s hardest moments into something worth celebrating.

    Event website ↗
Friday, September 25 4 events
  • 5:30pm

    Friday Night Kids Club

    ArtFarm Studios, 111 Chinquapin Round Rd, Annapolis · verified Sep 4
    See details

    Kids ages 6 to 10 can enjoy an evening of pizza, juice boxes, and snacks, hands-on fun at a game table and an art station, then a cozy movie to wind down. Attendance is limited to 12 so each child gets plenty of attention. Send a water bottle, and feel free to include favorite games. A yoga mat, blanket, or sleeping bag can make movie time extra comfy. Children may be dropped off in their pajamas for an easy, kid-free night out for parents.

    Event website ↗
  • 6pm

    Breathwork Circle with Trish Brewer at Restore studio

    Restore Studio at Meadow Hill Wellness, 53 Old Solomons Island Rd, Annapolis · verified Sep 4
    See details

    Guided by Trish, this breathwork experience uses deep, intentional breathing to support emotional release. Focused breathing can spark endorphins and help you connect with a deeper part of yourself where you can shift emotional defaults and patterns, listen to your intuition, and tap into creativity and clarity. It offers a welcoming space to reflect, release, breathe more fully, and build a sense of connection with yourself and the surrounding community.

    Event website ↗
  • 7pm

    Author Event: Jeneva Rose

    Maryland Hall, 801 Chase St, Annapolis
    See details

    Maryland Hall in Annapolis hosts a special evening with #1 New York Times bestselling author Jeneva Rose, presented by Park Books and spotlighting her new release, Sometimes I Scare Myself. A large turnout is anticipated, and tickets are required for entry. A $45 ticket includes a copy signed in advance of the new book, a professional photo with the author, exclusive event keepsakes and treats, and general admission seating. Personal copies from home will not be signed. To complete a signed collection, advance orders of backlist titles are recommended, with only 50 copies of each available for purchase. The book features three chilling tales. In Never Kill the Medium, a thirtieth birthday celebration turns catastrophic when a playful séance ends in tragedy, and an unfinished ritual invites something sinister. The Nightmare House follows the Dalton family to a seemingly perfect home in Tillington, where whispers in the walls and watchful neighbors unsettle the new mother, Kristin, as she discovers a grim history of former residents who died or vanished. All Curses Are Final finds a group of friends stopping at a roadside shop that claims every item is cursed until bought, then a storm isolates them at a winter cabin after an unpaid trinket appears, bodies begin to fall, and suspicion spreads.

    Event website ↗
  • 8pm

    Metropolitan Rooftop

    Metropolitan Kitchen and Lounge, 169 West St, Annapolis
    See details

    Leftovers is a party held on the rooftop.

    Event website ↗
Saturday, September 26 4 events
  • 11am

    Visiting Author - Marissa D’Angelo, Pirates and Myths

    Maryland Renaissance Festival, 1797 Crownsville Rd, Annapolis · verified Sep 4
    See details

    Visiting author Marissa D’Angelo will be on hand for a friendly meet and greet and book signing highlighting Pirates and Myths. Attendees can connect with the author and have books signed.

    Event website ↗
  • 11am

    Visiting Author - J.C. Wade, Historical Scottish Fiction Fantasy

    Page After Page, 1797 Crownsville Rd, Annapolis
    See details

    Visiting author J.C. Wade will be featured at a meet and greet with a book signing. Known for historical Scottish fiction with a fantasy focus, Wade will be available to chat, personalize books, and connect with readers.

    Event website ↗
  • 12pm

    36th Annual Kunta Kinte Heritage Festival

    Navy–Marine Corps Memorial Stadium, Annapolis · verified Aug 30
    Free

    The 36th Annual Kunta Kinte Heritage Festival is a free, family friendly celebration at Navy–Marine Corps Memorial Stadium. Attendees can enjoy music, food, arts, culture, and educational experiences for all ages.

    Event website ↗
  • 8pm

    Southern Culture on the Skids and more

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

    Southern Culture on the Skids appears with Poi Rogers for an all ages show highlighting the band’s playful mix of rock and roll, surf, country, folk, rockabilly, and R&B. Rick Miller on guitar and vocals, Mary Huff on bass and vocals, and Dave Hartman on drums have been at it for decades, taking their music from North Carolina house parties to late night TV, international stops near Mt. Fuji, and even shows inside state correctional facilities. They have shared stages with artists such as Link Wray, Loretta Lynn, Hasil Adkins, and Patti Smith, and their songs have surfaced in movies, television, and advertising, even drawing a parody from Weird Al. Critics have praised the biting guitar work, irresistible rhythms, and party-ready spirit of their concerts, with outlets like Rolling Stone noting the unrestrained energy of their live set. Their latest full length, At Home with Southern Culture on the Skids, arrived in 2021 after being recorded while off the road, and features Run Baby Run, a burst of garage grit powered by Mary Huff’s urgent vocal.

    Event website ↗
Sunday, September 27 4 events
  • 11am

    Visiting Author - K.W. Foster, Adult Romantasy

    Page After Page, 1821 Crownsville Rd, Annapolis
    See details

    Meet K.W. at a friendly author meet and greet with a book signing. Talk about the books, ask questions, and get books signed. Attendees can also learn more about K.W.’s books.

    Event website ↗
  • 11am

    Visiting Author - Anna Bright, Young Adult Medieval Wales

    Maryland Renaissance Festival, 1797 Crownsville Rd, Annapolis · verified Sep 4
    See details

    Meet the author in person and get books signed. Anna will be available to talk about her work and sign copies for attendees.

    Event website ↗
  • 2pm

    Oktoberfest Accordion Beats with Elena Stenkina

    Old Stein Inn, 1143 Mayo Rd, Edgewater · verified Aug 30
    See details

    A lively Oktoberfest gathering in the Biergarten features Elena on accordion, filling the scene with upbeat melodies and a festive atmosphere.

    Event website ↗
  • 2pm

    Oktoberfest with Elena on The Accordion

    Old Stein Inn, 1145 Mayo Rd, Edgewater · verified Sep 4
    See details

    Celebrate Oktoberfest in the Biergarten at Old Stein Inn with live accordion music from Elena. Enjoy lively melodies in a friendly Biergarten setting as Elena provides the soundtrack for the festivities.

    Event website ↗
Tuesday, September 29 1 event
  • 8pm

    Los Lonely Boys

    Rams Head On Stage, 25 West St, Annapolis · verified Aug 30
    See details

    Los Lonely Boys appear with Lisa Morales for a night built around the tight harmonies and guitar-forward sound the Garza brothers call Texican rock and roll. Henry, Jojo, and Ringo grew up in San Angelo, Texas, and turned their blend of blues, roots, and rock into international attention when their self-titled debut delivered Heaven, a No. 1 single that earned a Grammy and kept the album on the Billboard charts for well over a year. Early encouragement from Willie Nelson helped propel their rise, from Farm Aid stages to studio collaborations, and they have gone on to work with artists such as Carlos Santana. After years of near-constant touring, they paused in 2019 to focus on family, then returned to the road in 2022 with renewed energy, even sharing bills with The Who. Their path has also included resilience, including a serious onstage accident in 2013 that injured Henry and underscored their commitment to each other and to their music. Their story is captured in the documentary Cottonfields and Crossroads. Today they continue to write, record, and perform with purpose, highlighted by Resurrection in 2024, released through BMG, which reconnects with their signature sound while blending in soul and roots influences. All ages are welcome.

    Event website ↗
Wednesday, September 30 2 events
  • 10am

    Water Biiss & Events

    Quiet Waters Park, 124 Hillsmere Dr, Annapolis
    See details

    Quiet Waters Park in Annapolis offers on-the-water adventures with tours, social paddles, and Blue Angels shows. Launch a kayak, canoe, or stand up paddleboard from the park’s dock to explore the calm, protected waters of Harness Creek. Wildlife enthusiasts can look for more than 190 recorded bird species, including breeding bald eagles and osprey. Free outdoor concerts add to the experience. Set about four miles from Historic Annapolis, this waterside setting makes it easy for both residents and travelers to connect with the Chesapeake outdoors.

    Event website ↗
  • 9pm

    Hyland Brothers Live

    Stan and Joe's Saloon, 37 West St., Annapolis · verified Aug 30
    See details

    This event features a live musical performance. It offers a chance to hear music presented in real time.

    Event website ↗
Thursday, October 1 1 event
  • 8pm

    Victory Boyd

    Rams Head On Stage, 25 West St, Annapolis · verified Aug 30
    See details

    Victory Boyd brings her soul and folk artistry to the stage, drawing on the deep musical currents shaped by the African American experience to offer songs of hope and renewal. This performance is open to all ages. She began singing in her family choir as a child and later spent a decade sharing free concerts in Central Park after moving to New York City. Discovered there by filmmaker Jeymes Samuel, she was introduced to Jay-Z, who signed her along with her family. Her debut album, The Broken Instrument, expanded her audience worldwide and led to a collaboration helping write Kanye West’s Gospel album Jesus is King, earning her a Grammy as a songwriter. She went on to open The Secret Place Studios and release the album Glory Hour, followed by tours across Europe, including an appearance at the Premier Gospel Awards in London where she was nominated for International Artist of the Year. Her holiday collection, Christmas Hymns, highlights her reverence for sacred tradition, while her third studio album, Confessions of a Lonely Girl, delves into vulnerability, faith, love, and womanhood through intimate, soul-baring songs.

    Event website ↗
Friday, October 2 1 event
  • 8pm

    Hyland Brothers Live

    Harper's Waterfront Restaurant, 1107 Turkey Point Road, Edgewater · verified Sep 4
    See details

    Enjoy a performance featuring musicians playing live.

    Event website ↗
Saturday, October 3 1 event
  • 11am

    Visiting Author - T.L. Price, Romantic Fantasy

    Maryland Renaissance Festival, 1821 Crownsville Rd, Annapolis · verified Sep 4
    See details

    Meet the author in person for conversation and a signing. This is an opportunity to get a book signed and learn more about TL’s books.

    Event website ↗
Sunday, October 4 7 events
  • 10:15am

    Together in Teal Walk

    Annapolis Mall, 144 Annapolis Mall, Annapolis · verified Sep 4
    See details

    At Annapolis Mall, the National Ovarian Cancer Coalition presents its annual Together in Teal Walk, a community gathering devoted to saving lives through the prevention and cure of ovarian cancer and to supporting the quality of life of survivors and caregivers. Participants walk in solidarity with a shared hope of ending deaths from ovarian cancer, honoring survivors and remembering loved ones. This Annapolis walk is part of a series taking place in cities across the country, with an option to participate virtually when a local event is not available. Families, friends, and supporters raise critical awareness and help turn commitment into action in the fight against ovarian cancer.

    Event website ↗
  • 11am

    2026 Beagle Bash

    Crownsville Canine, 2007 Lineage Ln, Crownsville · verified Sep 4
    See details

    BRSM marks its 25th anniversary with the annual Beagle Bash, a lively celebration featuring food, treats, raffles, Snoopy, and spirited costume contests with plenty of howling. Well behaved dogs of all breeds are welcome. If it rains, the event will be rescheduled.

    Event website ↗
  • 11am

    Visiting Author - Rita Feinstein, Fantasy Poetry and Young Adult

    Maryland Renaissance Festival, 1821 Crownsville Rd, Annapolis · verified Sep 4
    See details

    Visiting author Rita Feinstein will be on hand for a meet and greet and book signing focused on her fantasy poetry and young adult work. Attendees will have a chance to say hello and get books signed.

    Event website ↗
  • 11am

    Visiting Author - Lisa Perrin, Poisons and Seances

    1821 Crownsville Rd, Annapolis
    See details

    An author meet and greet is paired with a book signing. Attendees can meet Lisa, learn more about her books, and have copies signed.

    Event website ↗
  • 11am

    Annapolis First Sunday Arts Festival

    Downtown Annapolis , 1603 West St, Annapolis · verified Sep 4
    See details

    The First Sunday Arts Festival transforms West Street and Calvert Street into a family-friendly celebration with more than 150 vendors, food trucks, live music, and cafe dining at seven restaurants. The Accidental Poet will have a booth on West Street near Author Alley and will share story readings for listeners of all ages. This series takes place on the first Sunday of each month from May through November.

    Event website ↗
  • 2pm

    Oktoberfest with The Polka Terps Band

    Old Stein Inn, 1145 Mayo Rd, Edgewater
    See details

    An Oktoberfest celebration takes place in The Biergarten, featuring live polka from The Polka Terps Band. Lively rhythms and a festive atmosphere set the tone for a spirited gathering centered on music and seasonal cheer.

    Event website ↗
  • 8pm

    The Buena Vista Orchestra

    Rams Head On Stage, 25 West St, Annapolis · verified Sep 4
    See details

    The Buena Vista Orchestra brings the spirit of Cuba’s celebrated repertoire to Rams Head On Stage, with a rotating cast of artists tied to the Buena Vista Social Club, AfroCuban All Stars, and the bands of Celia Cruz, Omara Portuondo, Chucho Valdés, Willie Colón and more. Presented by SSK Music Presents as part of a USA tour, the performance is led by virtuoso Cuban violinist Rolando Morejón Reyes, whose background includes leading the Orquesta de Enrique Jorrín and work with Omara Portuondo, Willie Colón, Cachao López and Oscar D’León. He appears alongside trumpeter Antonio Perigo, percussionist Miguel Valdés, pianist Helder Rojas, trombonist Yosmel Garcerarn, and Latin Grammy nominee and percussionist Pepe Epsinosa, among others, with many players connected to the original Buena Vista Social Club performances. This renowned project has toured internationally, earned wide recognition, achieved ticket and record sales in the millions, and inspired documentaries and stage productions. All ages are welcome.

    Event website ↗
Monday, October 5 1 event
  • 8pm

    40 Fingers

    Rams Head On Stage, 25 West St, Annapolis · verified Sep 4
    See details

    At Rams Head On Stage, 40 FINGERS, an Italian quartet of guitarists, showcases virtuosic fingerpicking and inventive four guitar arrangements that have drawn more than 100 million views online. The performance spans reimagined rock and pop favorites, film and TV themes, and the group’s own compositions. Queen endorsed the quartet and featured its version of Bohemian Rhapsody on Queen’s website, and the musicians have collaborated with artists including Andrea Bocelli, US singer Tory Kelly, and Andy Summers of The Police on Bring on the Night. A dynamic visual production crafted by top European lighting designers complements the music, guiding listeners through pieces such as Sultans of Swing, Africa, The Sound of Silence, Bohemian Rhapsody, The Last of the Mohicans, and Libertango. This event is open to all ages.

    Event website ↗
Tuesday, October 6 2 events
  • 7:30pm

    PFLAG Annapolis/AACo Support Meeting

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

    Three peer support options are offered in one location, with separate groups for youth, for adults, and for parents and allies. The gathering takes place at the Unitarian Universalist Church Annapolis, not in the FAHS House behind the church. The adult group meets on the ground level with entry directly from the parking lot through the double green doors. The youth group and the parents and allies group meet on the main level, with entry through the main entrance.

    Event website ↗
  • 8pm

    97Underground.com Presents LYNCH MOB

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

    Lynch Mob brings its guitar-charged hard rock to Rams Head On Stage with an event open to all ages. Founded by George Lynch in 1989 after his time with Dokken, the band debuted on Elektra Records with Wicked Sensation, a gold-certified release that earned strong acclaim and led to a catalog spanning more than a dozen albums across three decades. The sound blends classic rock, blues, and metal with plenty of energy and a taste for improvisation. The current lineup features Lynch with drummer Jimmy D'Anda, vocalist Gabriel Colon, and bassist Jaron Gulino. D'Anda supplies a funky, heavy backbeat. Colon got his start with Fast Taker, which scored a top ten rock radio single in Puerto Rico, and he has showcased his range with groups such as Gothic Knights, Culprit, White Wizzard, and Rowan Robertson. Gulino, from New Jersey, adds East Coast drive and a track record with Tantric that includes chart success and extensive touring. The performance is set to celebrate the band’s history with career-spanning songs alongside a generous helping of Dokken material.

    Event website ↗
Wednesday, October 7 1 event
  • 8pm

    Charlie Mars & Abe Partridge

    Rams Head On Stage, 25 West St, Annapolis · verified Sep 4
    See details

    At Rams Head On Stage, singer songwriters Charlie Mars and Abe Partridge share the bill. Charlie Mars crafts songs with a classic touch while avoiding a single genre, drawing from country, jam bands, and alt country influences such as Uncle Tupelo. An English major from SMU who values wordplay, he expanded into more atmospheric sounds after discovering Daniel Lanois, using songwriting to examine pride, fear, cynicism, and self doubt in pursuit of happiness. Over more than two decades he has released seven studio albums along with EPs and singles, performed alongside REM, KT Tunstall, and Steve Earle, and been featured by outlets including Forbes, USA Today, and American Songwriter. He has built a career in small venues and backyards, still aiming for bigger stages and a chance to reflect the people and culture that shaped him. Abe Partridge, a musician, songwriter, visual artist, and podcaster from Mobile, Alabama, drew strong praise for his 2018 debut Cotton Fields and Blood For Days. Reviews noted a raw, percussive guitar approach that can pivot to precise picking, paired with lyrics that provoke thought, sometimes with subtlety and sometimes with thunderous force. Two distinctive voices come together on the same stage at Rams Head On Stage.

    Event website ↗
Thursday, October 8 3 events
  • 10am

    Jim's Marine at the Annapolis Powerboat Show

    City Dock, Annapolis · verified Sep 4
    See details

    Jim's Marine presents a selection of Tidewater boats at the United States Powerboat Show at Annapolis City Dock. Visitors can step aboard various models, compare layouts, and get to know features designed for family outings on the Chesapeake Bay and beyond. The showcase is backed by 40 years of trust from generations of boaters.

    Event website ↗
  • 5pm

    250th Gala

    Historic London Town & Gardens, 839 Londontown Rd, Edgewater · verified Sep 4
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    In recognition of the 250th anniversary of the Declaration of Independence, Historic London Town & Gardens presents an evening that spotlights London Town’s colonial story through immersive experiences, live music, historic interpreters, and interactive programming across its waterfront grounds. Guests can take guided tours of the historic sites and surrounding gardens, learn about colonial cocktail traditions, enjoy live performances, meet living history interpreters, capture photo moments, and savor heavy hors d’oeuvres. A cash bar and a wine pull will be available. General admission is $150. The VIP experience is $250 and includes early entry, exclusive waterfront access, complimentary drinks, and enhanced food offerings. Proceeds support Historic London Town & Gardens and its work to preserve and share the stories that shape the community.

    Event website ↗
  • 8pm

    North Mississippi Allstars

    Rams Head On Stage, 25 West St, Annapolis · verified Sep 4
    See details

    North Mississippi Allstars perform at Rams Head On Stage for an all ages show. Formed in 1996 by brothers Luther and Cody Dickinson as a fluid collective grounded in their North Mississippi roots, the band draws on the legacy of their father Jim Dickinson and local mentors such as RL Burnside, Junior Kimbrough, Otha Turner, and Fred McDowell. Early on, Luther hit the road with RL Burnside’s Ass Pocket of Whiskey tour, and the group has toured steadily since 1998. After releasing their debut in 2000, they went on to share stages with Phil Lesh, Mavis Staples, Robert Plant, John Hiatt, the Allman Brothers, the Black Crowes, Buddy Guy, Snoop Dogg, and Jon Spencer, earning multiple Grammy nominations for their experimental sound they call Modern Mississippi Music. Over the years the touring lineup has featured Cedric, Duwayne and Garry Burnside, Chris Chew, Berry Oakley Jr, Oteil Burbruidgem, Joey Williams of the Blind Boys of Alabama, and Ray Ray Hollowman, a guitarist for Eminem and Nee-O.

    Event website ↗
Saturday, October 10 4 events
  • 11am

    Visiting Author - Meg Merriet Wahlberg, Sapphic Historical Fiction

    1821 Crownsville Rd, Annapolis
    See details

    This event offers a chance to meet the author, talk about her work, and take part in a book signing. Spend time with Meg to discuss her books and get a signature.

    Event website ↗
  • 11am

    Visiting Author - B.L. Mostyn, Young Adult Epic Fantasy

    1821 Crownsville Rd, Annapolis
    See details

    Meet the author and get a book signed. B.L. will be available to greet readers and share more about the book.

    Event website ↗
  • 11am

    Visiting Author - Enfys J. Book, Queer Magickal Resilience

    1821 Crownsville Rd, Annapolis
    See details

    Meet author Enfys for a relaxed meet and greet with book signing. Say hello, ask a question, and have a book signed.

    Event website ↗
  • 8pm

    Technicolor Motor Home: A Tribute to Steely Dan

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

    Technicolor Motor Home delivers a faithful salute to the recent touring sound of Steely Dan with a 10-piece lineup. Led by Crack The Sky keyboardist Glenn Workman, the group draws from every Steely Dan album and brings the music’s layered textures to life with horns and backing vocalists. Baltimore Magazine has praised their knack for tackling songs long considered challenging to reproduce on stage and for presenting them with meticulous detail and drive. This is an all-ages event.

    Event website ↗
Sunday, October 11 5 events
  • 11am

    Visiting Author - Erica Rose Eberhart, Queer Fantasy

    1821 Crownsville Rd, Annapolis
    See details

    Visiting author Erica Rose Eberhart hosts a friendly meet and greet and book signing with a focus on queer fantasy. Say hello, connect with the writer, and have a book signed.

    Event website ↗
  • 11am

    Visiting Author - Kathy MacMillan, Young Adult Fantasy and Children’s ASL

    1797 Crownsville Rd, Annapolis · verified Aug 30
    See details

    Meet the author in person and get books signed during a dedicated signing and greeting session. Learn more about Kathy and her books ahead of time.

    Event website ↗
  • 11am

    Visiting Author - E.E. Holmes, Historical and Contemporary Fantasy

    1821 Crownsville Rd, Annapolis · verified Aug 30
    See details

    Meet fantasy author E.E. Holmes during a visiting author appearance with a meet and greet and book signing. Learn about her books that span historical and contemporary fantasy, and have books signed.

    Event website ↗
  • 2pm

    Oktoberfest with Don Bitterlich on The Accordion

    Old Stein Inn, 1145 Mayo Rd, Edgewater
    See details

    Celebrate Oktoberfest in the Biergarten with live accordion music from Don Bitterlich. His performance on accordion sets the tone for the celebration.

    Event website ↗
  • 8pm

    The Carole King & James Taylor Story ft. Phoebe Katis & Dan Clews (8PM)

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

    The music and stories of Carole King and James Taylor take center stage in a live production performed by Phoebe Katis and Dan Clews. The show traces the careers of a six-time Grammy winner and 20-time platinum hitmaker alongside a five-time Grammy-winning American folk legend, celebrating a remarkable body of work. It includes favorites such as Fire and Rain, Sweet Baby James, I Feel the Earth Move, Natural Woman and You've Got a Friend, delivered with care and authenticity by two established artists. After acclaimed, sold-out runs at the Edinburgh Fringe and Adelaide Fringe, along with sell-outs across the UK and the US, the production comes with strong critical praise. Reviewers from The Upside News, BroadwayBaby, BBC Radio and Three Weeks have lauded the performance, and Sir George Martin praised Dan Clews as a talent too great to ignore. It is open to all ages.

    Event website ↗
Tuesday, October 13 1 event
  • 11:30am

    Lunch & Learn

    Maggiano's Little Italy, Annapolis · verified Aug 30
    Free

    Enjoy a complimentary lunch while learning practical ways to honor a loved one, plan ahead, and approaches that can save your family thousands. Ryan Helfenbein, a partner with Lasting Tributes and Fellows, Helfenbein & Newnam Funeral Home and a columnist for Outlook by the Bay magazine, leads an educational presentation covering green burial, veteran’s benefits, creating a meaningful celebration of life, preplanning, prepayment, and more. Difficult questions are welcome and will be addressed. Space is limited. The menu features freshly baked ciabatta rolls, an individually served Italian tossed salad, a choice of Mom’s Meat Lasagna with marinara or Fettuccini Alfredo with or without chicken, and Vera’s Lemon Cookies for dessert. Please enter through the mall entrance, and check in at the banquet room.

    Event website ↗
Wednesday, October 14 2 events
  • 7pm

    Versed Fox Book Club

    35 Maryland Ave, Annapolis · verified Aug 30
    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 ↗
  • 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 2 events
  • 10am

    Annapolis Sailboat Show

    Annapolis Boat Show, 110 Compromise St, Annapolis · verified Aug 30
    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 ↗
  • 8pm

    Comedian Josh Blue of Last Comic Standing

    Rams Head On Stage, 25 West St, Annapolis · verified Aug 30
    See details

    Rams Head On Stage hosts a stand-up set from Josh Blue, the 2006 champion of Last Comic Standing. His material is always evolving and his sharp improvisation keeps every performance unique, supported by a touring schedule that tops 200 shows each year. Highlights include a 2018 appearance on The Tonight Show Starring Jimmy Fallon, a set at the William H. Macy Gala during the Just for Laughs festival in Montreal, and the taping of his fifth hour special, Broccoli, at Comedy Works in Denver. In 2021 he earned third place on NBC’s America’s Got Talent and launched the As NOT Seen on TV Tour. He has also represented the United States in eight countries as a member of the U.S. Paralympic Soccer Team. This show is for ages 18 and over.

    Event website ↗
Friday, October 16 2 events
  • 6pm

    GhanaFest DMV - Weekend

    Rosecroft Raceway, 6336 Rosecroft Dr, Fort Washington
    See details

    Celebrate Ghana in the DMV with an experience designed to connect guests to Ghanaian culture and its people. This gathering highlights heritage and community, creating a welcoming space to share traditions and build meaningful connections.

    Event website ↗
  • 6pm

    World Cruising Club Rendezvous - USA

    20 Market Space, Annapolis · verified Aug 30
    See details

    Reconnect with fellow sailors, meet new cruising companions, and exchange stories from life at sea. It welcomes those planning a first ocean crossing, preparing for a next rally, or simply interested in conversations about cruising, boats, and adventures.

    Event website ↗
Saturday, October 17 6 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 ↗
  • 11am

    Visiting Author - Erin P.T. Canning, Epic Romantasy

    1821 Crownsville Rd, Annapolis
    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

    Visiting Author - A.M. Robin, Middle Grade Fantasy

    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 ↗
  • 6pm

    Party in the Port 2026

    317 1st St, Annapolis
    See details

    This event is open to the public. After the boat show, the celebration continues at Eastport Yacht Club with live music, waterfront views, and the easygoing, high energy vibe the club does best. Slip Hippies kicks things off with an Annapolis acoustic blend of classic rock, 80s, country, beach and island tunes, soul, Motown, and modern favorites. ONO, short for One Night Only, follows with big vocals, tight grooves, and a dance floor ready set that keeps the waterfront moving. Fall weather and harbor views pair with Chili in the 'Port, a build-your-own chili bar with all the fixings, plus the club’s well loved libations. Ticket options include advance purchase at 20 dollars plus a processing fee, an online only two ticket bundle for 35 dollars plus fees that is not sold at the gate, and a 25 dollar gate price. Kids ages 5 and under are admitted free. All guests enter through the main gate, with no access from the marina docks. The event is rain or shine and tickets are nonrefundable. Pets are not allowed. The party is 100 percent compostable with no single use plastic, and green volunteers will manage ecostations to keep things trash free. Attendees can also see the club’s Clean Marina and Green Building features, including a pervious parking lot, rain barrels, and landscaping that reduces runoff.

    Event website ↗
  • 6pm

    Boney James (6:00 PM)

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

    Rams Head On Stage hosts saxophonist and composer Boney James for an all ages performance of contemporary jazz. Over more than three decades he has earned four GRAMMY nominations, multiple NAACP Image Award nominations, a Soul Train Award for Best Jazz Album and four RIAA Gold records, and he became the first artist to achieve 20 number one singles on the Billboard Smooth Jazz chart. Recent work on his Concord Records album Slow Burn highlights his collaborative range, from Marcus Miller’s rare acoustic bass on Arcadia to a reimagining of Butterfly by Herbie Hancock and Bennie Maupin with Cory Henry on electric piano. The album features co-writes with multi-instrumentalist Jairus Mozee, a lead single with R&B vocalist October London, the funk driven Slide with his touring band, the tender A Little Romance, upbeat cuts like Gonna Have a Good Time and The Bounce, and a grooving tribute to Stanley Turrentine on Sugar with trumpeter Rick Braun. Known for a sound that builds with deliberate intensity, Boney James continues to connect with audiences through soulful melodies and groove.

    Event website ↗
  • 9pm

    Boney James (9:00 PM)

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

    Contemporary jazz saxophonist and composer Boney James takes the stage for an all-ages performance that channels the steady, deliberate intensity at the heart of his music. Recognized with multiple GRAMMY and NAACP Image Award nominations, a Soul Train Award, and several RIAA Gold records, he has also earned a historic run of number one singles on the Billboard Smooth Jazz chart. His recent Concord Records release, Slow Burn, captures that gradual build with notable collaborations, including Marcus Miller on upright bass, Cory Henry on electric piano, multi-instrumentalist and producer Jairus Mozee, vocalist October London, and longtime friend Rick Braun. The album moves from the warm pulse of Arcadia and a fresh take on Herbie Hancock and Bennie Maupin’s Butterfly to the swagger of Slide, the tender A Little Romance, the upbeat Gonna Have a Good Time and The Bounce, and Between the Lines, while tipping the hat to Stanley Turrentine on Sugar. From his early start to a career spanning decades, James continues to connect with listeners through expressive saxophone lines and groove-rich melodies. All ages are welcome.

    Event website ↗
Sunday, October 18 4 events
  • 11am

    Anchors & Artisans @ Annapolis Town Center

    Annapolis Town Center · verified Aug 30
    Free

    Spend the day browsing creations from more than 50 local makers and artists at Annapolis Town Center while live bands provide the soundtrack for a relaxed, family-friendly outing. Explore themed craft activities for kids and adults and enjoy interactive fun such as face painting. Grab a bite from eateries around the center and check out the shops along the way. Bring a blanket to stretch out on the turf, picnic, and enjoy the sunshine and community vibe. Admission is free, and parking garages around the shopping center are also free. All ages are welcome, with children accompanied by a parent or supervising adult. Dogs are welcome in the outdoor common areas, although individual stores may set their own rules for non-service pets. For specific guidelines, refer to Annapolis Town Center policies.

    Event website ↗
  • 11am

    Visiting Author - Shelley Puhak, Historical True Crime

    1821 Crownsville Rd, Annapolis
    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

    Visiting Author - Fiona Fenn, Queer Adult Romantasy

    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 ↗
  • 8pm

    Five For Fighting with String Quartet w/ Lace & Lee

    Rams Head On Stage, 25 West St, Annapolis
    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 1 event
  • 7:30pm

    Pete Best and Dana Cooper at 49 West

    49 West Coffeehouse, Winebar & Gallery, 49 West St, Annapolis
    See details

    Presented by ITZALL Goode and SHC Music Tribe, this concert brings together Pete Best and Dana Cooper for an evening of songs and stories. Pete Best is a Maryland-raised singer and songwriter whose sound blends southern rock grit with country storytelling, drawing on real life themes from family and resilience to turn-it-up bar anthems. Before relocating to Nashville, he became a familiar voice around Baltimore and Washington, opened shows for artists like Jack Ingram and Pat Green, and released his debut album Built to Last. His focus remains on writing songs that truly connect rather than chasing trends. Dana Cooper is an acclaimed artist with a catalog of more than thirty albums, known for heartfelt narratives and a warm stage presence. His recent release The Ghost of Tucumcari features a strong lineup of collaborators and moves easily among folk, rock, country, and Americana. Onstage he blends flat-picking, fingerstyle, percussive strumming, and harmonica, pairing accomplished musicianship with easygoing humor. Advance online tickets are $20 plus fees, and admission at the door is $25. Those not purchasing in advance may reserve seats by phone at (410) 626-9796 and will be charged the door price. Online purchases serve as reservations, and the venue requests that online ticket holders not call to book.

    Event website ↗
Tuesday, October 20 3 events
  • 10am

    Tots@10:00 - Farmyard Fun

    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 ↗
  • 7:30pm

    PFLAG Annapolis/AACo Support Meeting

    Unitarian Universalist Church of Annapolis, 333 Dubois Rd, Annapolis
    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
    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 ↗
Wednesday, October 21 1 event
  • 8pm

    Comedian James Austin Johnson of SNL

    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 1 event
  • 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 4 events
  • 6:30pm

    Phil Vassar (6:30PM)

    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, 10 Hudson St, Annapolis · verified Sep 4
    See details

    Bountiful Harvest: Costumes & Cocktails presents an evening dedicated to the largest fundraiser of the year, featuring an open bar, gourmet cuisine, and both silent and live auctions. Guests can arrive in creative costumes or polished cocktail attire. The event includes live music by the Noelle and Jeff Band. All proceeds benefit The Annapolis Light House, a homeless prevention support center. Tickets and sponsorships are available, and a VIP experience is offered.

    Event website ↗
  • 8pm

    Hyland Brothers Live @ Waterman’s

    Annapolis, MD
    See details

    Enjoy music performed live.

    Event website ↗
  • 9:30pm

    Phil Vassar (9:30PM)

    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 ↗
Saturday, October 24 3 events
  • 11am

    Visiting Author - K.M. Hogenson, High Epic Fantasy

    1797 Crownsville Rd, Annapolis
    See details

    Visiting author K.M. Hogenson will be on hand for a high epic fantasy meet and greet and book signing. Talk with the author about their books and get books signed.

    Event website ↗
  • 11am

    Visiting Author - Doc Coleman, Steampunk Comedy Adventures

    1797 Crownsville Rd, Annapolis
    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 ↗
  • 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 ↗
Tuesday, November 3 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 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 1 event
  • 8pm

    Gaelic Storm

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

    Gaelic Storm takes the stage with energetic Celtic music, vivid storytelling, and a devotion to tradition that has grown stronger through more than twenty years and over two thousand live shows. Their audiences span many musical tastes, and the group is known for a close bond with its fans. From early days playing pubs in Santa Monica in the mid 1990s to a breakout on the big screen in Titanic with Irish Party in Third Class, the band has built a far-reaching career. Along the way they have reached the top of the Billboard World Chart six times, appeared at mainstream festivals, and often headline major Irish gatherings, blending Irish roots with a creative rock sensibility. Recent additions include Natalya Kay on fiddle and Parker Hastings on guitar, each bringing fresh energy and musicianship to the lineup. This event is open to all ages.

    Event website ↗
Thursday, November 5 1 event
  • 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 ↗
Saturday, November 7 1 event
  • 10am

    Adopt A Lab Day

    PetSmart Annapolis Maryland #0359, 2601 Housley Rd, Annapolis · verified Aug 30
    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 ↗
Thursday, November 12 2 events
  • 3am

    Fall Harvest Weekend Crop

    Hampton Inn & Suites by Hilton Annapolis (124 Womack Dr, Annapolis, MD), 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, MD), 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 ↗
Saturday, November 14 2 events
  • 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 ↗
  • 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 ↗
Monday, November 16 1 event
  • 8pm

    Rams Head Presents Lalah Hathaway (Annapolis, MD)

    801 Chase St, Annapolis
    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 1 event
  • 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 ↗
Thursday, November 19 2 events
  • 7pm

    Hyland Brothers Live @ Harper’s Waterfront

    Harper's Waterfront Restaurant, 1107 Turkey Point Road, Edgewater
    See details

    This event features live music.

    Event website ↗
  • 8pm

    DMTB: The Dave Matthews Tribute Band: Tomorrow We Die Tour (Rescheduled from January 25, 2026)

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

    Lonesome River Band, the long-running bluegrass quintet associated with Mountain Home Music Company, performs at Rams Head On Stage. Guided by award-winning banjo player Sammy Shelor, the group has honed an influential sound over more than four decades and continues to reach audiences in person and online. The current lineup features Jesse Smathers and Adam Miller sharing lead vocals with Kameron Keller, Mike Hartgrove, and Shelor. The band has released The Winning Hand, a collection that blends the hallmarks of its established style with new directions, including titles such as Blues of the Night, That’s Why Trains Are Lonesome, Oh, Darlin’, Brown Hill, Near Mrs., She Don’t Know I’m Alive, A Happy Song, Nothin’ Comes To Mind, Charlottesville, and the fiddle and banjo showcase Tom and Jerry. The current single, Queen Of Hearts, features Smathers and was co-written with Miller after inspiration from a card game, a song Miller began in high school and reshaped with Smathers. This event is open to all ages.

    Event website ↗
Saturday, November 21 3 events
  • 9:30am

    Meet and Ride

    Chesapeake Cycles, 104 Defense HWY, Annapolis · verified Aug 30
    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 ↗
  • 8pm

    Noelle & Jeff Band @ Greene Turtle Edgewater

    The Greene Turtle (Edgewater), 3213 Solomons Island Rd., Edgewater · verified Aug 30
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    Noelle & Jeff Band returns to The Greene Turtle in Edgewater with Jeremy and Mike for a full night of throwback hits. Expect a relaxed yet lively atmosphere with live music that keeps the energy high, covering favorite songs from the 1980s, 1990s, and 2000s. A cool-weather vibe and warm drinks set the tone for a feel-good night out.

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  • 8pm

    Marshall Crenshaw w. Sarah Borges

    Rams Head On Stage, 25 West St, Annapolis · verified Aug 30
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    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.

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Sunday, November 22 2 events
  • 10am

    Soften and Rise Retreat

    Annapolis, MD 21401 United States, 553 Choptank Cove Ct, Annapolis · verified Aug 30
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    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.

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  • 4:30pm

    Herman's Hermits Starring Peter Noone (4:30PM)

    Rams Head On Stage, 25 West St, Annapolis · verified Aug 30
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    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.

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