Events in Leonardtown, MD

● Listings verifiedThursday, September 17 · every listing checked against its source by our Leonardtown editors

26This week
75Next 30 days
2Free this week
58Venues tracked
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This weekend in Leonardtown

The ones worth planning around. All 12 weekend events →

Live music in Leonardtown

3 shows this week.

  • Thu 7pm

    Audra & Johnny every 3rd Thursday at Buckets

    Buckets Bar and Grill, 12020 Rousby Hall Rd, Lusby · verified Sep 13
    See details

    Audra & Johnny perform as a duo at Buckets Bar and Grill on the third Thursday. This ongoing appearance features the two of them on stage together.

    Event website ↗
  • Sat 6pm

    Jimmy and Tricia 🎤🎶

    16829 Kings Hwy, Montross · verified Sep 13
    See details

    The Barn hosts Jimmy and Tricia for an evening filled with live music, good food, and a fun atmosphere.

    Event website ↗
  • Sun 10am

    Cars & Coffee Car Show

    22675 Washington St, Leonardtown · verified Sep 13
    See details

    A friendly car gathering offers a chance to admire showcased vehicles and spend time with friends. On-site activities include a 50/50 drawing, prize giveaways, cornhole games, and music. Vendor inquiries are handled by direct message, and spaces measure 10 by 10.

    Event website ↗

All upcoming events, day by day

Every event we track in Leonardtown this week, in order. After one kind of thing? family events has their own calendar.

Thursday, September 17 4 events
  • 10:15am

    Little Minnows

    Calvert Marine Museum, 14200 Solomons Island Road, Solomons · verified Sep 13
    See details

    Designed for preschoolers ages 3 to 5 with an accompanying adult, this Calvert Marine Museum program explores one of the museum’s three core themes through an engaging read-aloud and a make-and-take craft while supplies last. Each session runs about 25 to 40 minutes and participation is included with museum admission, so advance registration is not required. This recurring offering takes place on the third and fourth Thursday of each month. Space is limited and same-day sign up is handled at the Admissions Desk upon arrival. From May through August, weather permitting, activities are held outdoors at the Corbin Nature Pavilion. During the rest of the year and in inclement weather, the group meets indoors in the Harms Gallery.

    Event website ↗
  • 5pm

    Twice Loved Kids Consignment All Seasons Sale in Prince Frederick, MD!

    185 Holy Family Ln, Prince Frederick · verified Sep 13
    See details

    A family-friendly kids consignment sale in Prince Frederick, MD offers multiple shopping sessions focused on value and variety for all seasons. The first session provides early entry for a $5 cash fee per adult, with children admitted free. The public sale that follows is free to enter. A dedicated discount day starts with 25 percent off on items labeled "DISCOUNT YES" and later increases to 50 percent off on those same marked items. The final day continues with free-entry savings at 50 percent off on "DISCOUNT YES" selections and concludes with a Dollar Dash, where anything tagged with a "D" is available for one dollar, cash only.

    Event website ↗
  • 6:30pm

    TACOS Teen Advisory Council of Students (PF)

    Calvert Library, 850 Costley Way, Prince Frederick · verified Sep 13
    See details

    Teens are invited to help shape Calvert Library by taking part in TACOS, the Teen Advisory Council of Students. This monthly gathering focuses on keeping the library a welcoming place to relax, connect with peers, and easily access books and information while offering input on events and services. Meetings are held every third Thursday, and participants earn one Service Learning hour for each meeting attended. Calvert Library strives to make all events accessible. For questions about access or requests, call 410-535-0291.

    Event website ↗
  • 7pm

    Audra & Johnny every 3rd Thursday at Buckets

    Buckets Bar and Grill, 12020 Rousby Hall Rd, Lusby · verified Sep 13
    See details

    Audra & Johnny perform as a duo at Buckets Bar and Grill on the third Thursday. This ongoing appearance features the two of them on stage together.

    Event website ↗
Friday, September 18 6 events
  • 8am

    Golf tournament

    Chesapeake Hills Golf Club, 11352 HG Trueman Rd, Lusby · verified Sep 13
    See details

    The annual golf tournament returns to Chesapeake Hills Golf Club. Participants can register at the post or complete registration online. Sponsorship opportunities are available, and sponsor packets can be picked up or requested by email.

    Event website ↗
  • 9:30am

    TRX Pilates Strength & Stretch

    41566 Medleys Neck Rd, Leonardtown · verified Sep 13
    See details

    A TRX Pilates session blends Pilates fundamentals with the dynamic support of suspension training. The focus is on strength, core, balance, breath, and a steady burn. Movements emphasize core activation, mindful breathing, concentration, and stability while the TRX adds both assistance and challenge. Each exercise is crafted to build strength and increase flexibility, providing support for safe, effective work from start to finish.

    Event website ↗
  • 11am

    Last Getaway Retreat

    Hilton Garden Inn Solomons (Dowell, MD), 13100 Dowell Rd, Dowell · verified Sep 13
    See details

    Last Getaway Retreat is an in-person, three day scrapbooking and card-making experience at Hilton Garden Inn Solomons in Dowell, Maryland. Registration is $175, with a $50 nonrefundable deposit required at sign up. Paying in full at registration includes an exclusive retreat gift. A limited number of day spots are available for $65 per day on a first come, first served basis. Participants receive a 6 foot workspace with access to power, themed materials, a welcome gift, door prizes, and games, along with classes, demonstrations, and hands-on make and take projects. Hosted by Kimberly Leatherwood. A variety of supplies will be available on site, including album covers, pages, paper packs, stickers, embellishments, tools, storage solutions, pens, and more. Discounted hotel rooms will be offered, with options that include two queen beds or a king bed with a sofa, and a booking link will be provided when available. For questions, email Kimberly@scrapbookingwithkimberly.com or call or text 240-498-0294. Open to scrapbookers and crafters.

    Event website ↗
  • 12pm

    Calvert County Lions Club Blood Drive

    98 Solomons Island Rd S, Prince Frederick · verified Sep 13
    Free

    This community blood drive is organized by the Calvert County Lions Club. Registration is available to reserve a spot.

    Event website ↗
  • 1pm

    Pins and Needles (PF)

    Calvert Library, 850 Costley Way, Prince Frederick · verified Sep 13
    See details

    Crafters are welcome to bring quilting, needlework, knitting, crocheting, or another project to enjoy conversation and create together at Calvert Library. Library resources on these topics are available. For accessibility accommodations, please contact the library at least two weeks in advance at 410-535-0291.

    Event website ↗
  • 6pm

    Sip & Paint Spooky Ceramic Lanterns at WhataBoba Lusby

    Lusby · verified Sep 13
    See details

    Create a spooky ceramic lantern at a relaxed sip and paint gathering at WhataBoba Lusby Tea Shop. Choose your lantern design during checkout, enjoy boba tea as you work, and follow along with step by step guidance. All materials are included, it is suited to beginners, and no prior experience is needed. You will head home with your completed ceramic lantern.

    Event website ↗
Saturday, September 19 10 events
  • 9am

    Stab & Gab - Sept 2026

    Leonardtown Library, 41685 Library Pl, Leonardtown · verified Sep 13
    See details

    Fall is in the air, and the fair is just around the corner next weekend. Take this moment to prepare and polish your submissions.

    Event website ↗
  • 9am

    13th Annual AGB Croquet Tournament

    Town Hill, Colonial Beach, 401 Washington Ave, Colonial Beach · verified Sep 13
    See details

    Town Hill in Colonial Beach hosts the 13th annual croquet tournament benefiting the Colonial Beach Volunteer Fire Department. The event seeks players, volunteers, and sponsors. Matches are played under USCA 9-wicket rules, also known as long grass or backyard croquet. Up to 36 pre-registered participants will be randomly placed into six preliminary matches, and each winner will advance to a final for the Alexander Graham Bell Trophy. Bloody Marys, Mimosas, sodas, beer, and water will be available for purchase, and lunch will be sold during the midday break. The registration fee is $35 per player per match. Sponsorships include one player registration and are offered at several levels, including $100 to sponsor a match, $100 to support the food or beverage tent, $100 to provide a shade tent for spectators, and $300 to sponsor the championship match, with limited quantities available. Payment can be made online or by mail to the Colonial Beach Volunteer Fire Department, and in-person registration is available at Beach Paws Boutique. Donations to the fundraiser are also welcome.

    Event website ↗
  • 10am

    Stratford Hall Wine & Oyster Festival

    483 Great House Rd, Montross · verified Sep 13
    See details

    Celebrate Virginia wine and coastal flavors at a lively festival featuring tastings from more than a dozen local wineries paired with fresh oysters. Enjoy spirits from distilleries, live music, artisan vendors, a variety of food trucks, family activities, car shows, and more. Early bird tasting tickets are $35 from July 1 through September 18, general tasting admission is $50, non-tasting entry is $25, tickets for children ages 7 to 12 are $10, and children 6 and under are free. Information about vendors and sponsors is available, along with options for ticket upgrades, breakfast, and lodging enhancements.

    Event website ↗
  • 10am

    10th Annual Wheels and Wings Car Show

    22156 Three Notch Rd, Lexington Park · verified Sep 13
    See details

    The Patuxent River Naval Air Museum hosts the 10th annual car show featuring vehicles from across the region. Displays are arranged along the museum’s flight line and among the aircraft, offering a side-by-side look at cars and aircraft in a unique setting.

    Event website ↗
  • 10am

    Artsfest '26

    13470 Dowell Road, United States · verified Sep 13
    See details

    Now in its 34th year, Artsfest transforms the 30-acre grounds of Annmarie Sculpture Garden & Arts Center into a vibrant celebration of creativity. Explore over 170 artist booths and a lineup of 40 live performers. Street performers roam the grounds, from bubble artists to musicians, and families will find interactive activities for kids. Local food, wine, and brews add to the festival atmosphere for a full weekend of visual and performing arts and family-friendly fun. Admission details: members are free with an online reservation. A weekend pass is $15. Saturday tickets are $10 when purchased online in advance ($13 at the gate if not sold out). Sunday tickets are $10. Children 11 and under are free.

    Event website ↗
  • 10am

    The Magnolia Market 2026

    Serenity Farm at Benedict, 6932 Serenity Farm Road, Benedict · verified Sep 13
    See details

    Serenity Farm in Benedict hosts the 5th annual Magnolia Market, a family friendly celebration of shopping, food, and community. Browse handmade creations from local crafters, artists, and upcyclers alongside vintage pieces and clothing, enjoy tastings of beer, wine, and spirits, and explore a range of options from several food trucks. Live music sets the tone throughout the day while scenic hayrides, a petting pen, and seasonal activities add farm fun for all ages. Raffles, 50/50 drawings, and other games keep the excitement going, and cash is recommended for these activities. Admission is $10 per person in advance and $15 per person on the day of the event. Children 12 and under receive free admission and a pumpkin while supplies last. The first 250 attendees receive a free swag bag. Proceeds support #deMANDAcure Inc., and every attendee also helps benefit The Amanda Shay (Odom) Wilkins Book Legacy & Memorial Scholarship Fund.

    Event website ↗
  • 2pm

    On Pins and Needles (SO)

    Calvert Library - Southern Branch, Solomons · verified Sep 13
    See details

    On Pins and Needles at Calvert Library’s Southern Branch brings fiber enthusiasts together to practice, share, and build skills. Whether you knit, embroider, or crochet, beginners and experienced makers can trade tips, learn new techniques, and either continue a work in progress or start something new. Registration is requested, and participants should bring their own yarn. For accessibility questions or requests, contact 410-535-0291.

    Event website ↗
  • 3pm

    Outdoor Art & Movie Night

    Town Market LLC, 22675 Washington St, Leonardtown · verified Sep 13
    Free

    Unwind under the night sky with a free outdoor movie at Town Market. Before the film begins, take part in sidewalk chalk and creative art activities. Bring a blanket or lawn chair for comfortable seating. Food and drinks will be available for purchase, making it easy to turn the experience into a relaxed family outing. The movie will be family friendly, and the specific title is still to be determined.

    Event website ↗
  • 5:30pm

    5th Annual One More Light Suicide Prevention Walk

    Southern Maryland Sailing Association - SMSA, 14490 Solomons Island Road S., Solomons · verified Sep 13
    See details

    The 5th annual One More Light Walk gathers the community for an evening centered on honoring loved ones, standing with those who are struggling, and nurturing hope. Participants come to remember, to support, or to discover renewed strength on their own path. More than a walk, it is a shared commitment to break the silence and ensure no one faces the dark alone. Families, friends, and individuals are welcome. This free event invites everyone to take a step toward purpose, strength, and living hope.

    Event website ↗
  • 6pm

    Jimmy and Tricia 🎤🎶

    16829 Kings Hwy, Montross · verified Sep 13
    See details

    The Barn hosts Jimmy and Tricia for an evening filled with live music, good food, and a fun atmosphere.

    Event website ↗
Sunday, September 20 2 events
  • 10am

    Cars & Coffee Car Show

    22675 Washington St, Leonardtown · verified Sep 13
    See details

    A friendly car gathering offers a chance to admire showcased vehicles and spend time with friends. On-site activities include a 50/50 drawing, prize giveaways, cornhole games, and music. Vendor inquiries are handled by direct message, and spaces measure 10 by 10.

    Event website ↗
  • 12pm

    Calvert County Watermen's Association's Festival and Boat Docking Competition

    Solomons, Maryland, Solomons · verified Sep 13
    See details

    The event begins with an opening ceremony. A warm welcome awaits those returning this year, and everyone is encouraged to help spread the word by inviting friends and sharing the news.

    Event website ↗
Monday, September 21 2 events
  • 3pm

    Monday Madness

    26005 Point Lookout Rd, Leonardtown · verified Sep 13
    See details

    A special focused on pizza and wings, with the choice to enjoy your meal on site or take it to go.

    Event website ↗
  • 6:30pm

    Bilingual Conversation Hour: Spanish-English (PF) - Bring a friend and practice with us!

    Calvert Library, 850 Costley Way, Prince Frederick · verified Sep 13
    See details

    Enjoy a friendly hour of bilingual conversation split into 30 minutes of English and 30 minutes of Spanish. Participants build conversation skills while community members support one another’s language goals. It is a good fit for anyone brushing up on Spanish from school, reconnecting with Latin American heritage and aiming for greater fluency, strengthening English skills, or hoping to help others feel confident speaking either language. Calvert Library is committed to accessibility for all. For accessibility questions or requests, call 410-535-0291. Calvert Library da la bienvenida a todas las personas, incluidas las personas con discapacidades. Para preguntas o solicitudes de accesibilidad, llama al 410-535-0291.

    Event website ↗
Tuesday, September 22 1 event
  • 2pm

    Savasana Sanctuary Yoga: A Nervous System Reset

    Leonardtown Library and Garvey Senior Activity Center, Leonardtown · verified Sep 13
    See details

    Settle into a quietly restorative yoga session designed to soothe the body and calm the mind. Over the course of ninety minutes, participants move through simple, accessible movements and gentle breathing practices, then ease into an extended guided rest that supports stress relief and nervous system balance. During the final relaxation, optional hands-on support may be offered with light holds at the shoulders, head, neck, and feet to encourage release and comfort. All activities are adaptable for different abilities. Expect a brief warmup to reduce stiffness, unhurried stretches that prepare the body to rest, soft breath cues that invite ease, and ample time for full-body relaxation. Many older adults may appreciate benefits such as less muscle tightness, better sleep and mental clarity, emotional steadiness, and a lingering sense of comfort that can leave participants feeling grounded and light. Instruction is provided by Judi Chaudrue-Lyons, who offers gentle, attentive guidance with a focus on safety, comfort, and deeply relaxing hands-on care.

    Event website ↗
Wednesday, September 23 1 event
  • 11:30am

    Tech Help Drop-in Hour (PF) - Skillbuilders presents

    Calvert Library, 850 Costley Way, Prince Frederick · verified Sep 13
    See details

    Calvert Library offers drop-in tech help for troubleshooting devices and navigating everyday digital tools. Staff provide personalized assistance with computer and internet basics, e-readers and Libby, Microsoft Office or Google apps, and other personal device questions. No appointment is needed for this dedicated hour. One-on-one tech trainings can also be scheduled during regular open hours at all locations, but this time is set aside specifically for your questions. These sessions take place on the second Mondays and fourth Wednesdays of every month in Prince Frederick. For accessibility questions or requests, call 410-535-0291.

    Event website ↗

All upcoming events89 more events through Dec 5

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

Thursday, September 24 7 events
  • 10am

    JobSource Mobile Career Center (SO)

    Calvert Library - Southern Branch, Solomons · verified Sep 13
    See details

    Explore job opportunities with the JobSource Mobile Career Center at Calvert Library - Southern Branch. Job seekers can receive counseling, get help refining resumes, search for jobs, and connect with Southern Maryland JobSource. The 38-foot mobile unit includes 11 computer workstations with satellite internet access, a smart board for instruction, exterior audiovisual and broadcasting capabilities, state-of-the-art workforce applications, and wireless connectivity for mobile devices. For accessibility accommodations, call 410-535-0291 at least two weeks in advance.

    Event website ↗
  • 10:15am

    Little Minnows

    Calvert Marine Museum, 14200 Solomons Island Road, Solomons · verified Sep 13
    See details

    Designed for preschoolers ages 3 to 5, this Calvert Marine Museum program explores one of the museum’s three themes through story time and a simple take-home craft available while supplies last. Each session runs about 25 to 40 minutes, and every child must be accompanied by an adult. Participation is included with museum admission, and no registration is required. Capacity is limited, so sign up at the Admissions Desk upon arrival. This program takes place on the third and fourth Thursday of each month. From May through August, weather permitting, activities are held outdoors at the Corbin Nature Pavilion. During the remainder of the year and in inclement weather, sessions meet indoors in the Harms Gallery.

    Event website ↗
  • 11am

    Whole Body Bliss: Intro to Self-Myofascial Release

    Loffler Senior Activity Center, Great Mills · verified Sep 13
    See details

    Returning by request, this interactive workshop with Judi Chaudrue-Lyons introduces self myofascial release, a do-it-yourself massage approach that targets muscles and connective tissue to help ease localized discomfort. Participants explore the core principles and hands-on techniques that can make everyday movement feel more comfortable. SMR is associated with benefits such as improved mobility, posture, alignment, musculoskeletal function, energy, immune support, circulation, and nerve function. Techniques covered are commonly used for concerns like arthritis and joint pain, back pain, carpal tunnel syndrome, chronic fatigue, congestion, fibromyalgia, frozen shoulder, headaches and migraines, plantar fasciitis, repetitive motion injuries, restless leg syndrome, sciatica or piriformis-related discomfort, scoliosis, and TMJ issues. Open to all, with a suggestion to wear flexible clothing and bring water. The fee is $25, and it includes massage balls and a full color illustrated digital instruction handbook.

    Event website ↗
  • 4pm

    St. Mary's County Fair - 2026

    St Marys County Fair, 42455 Fairgrounds Road, Leonardtown · verified Sep 13
    See details

    St. Mary's County Fair for 2026 takes place at St Marys County Fair. Those planning to enter items will have a designated window to submit them. A new virtual system is expected to allow you to submit your list of items, so keep an eye out for instructions on this entry method.

    Event website ↗
  • 5pm

    TACOS Teen Advisory Council of Students

    Calvert Library - Southern Branch, 13920 H G Trueman Rd, Solomons · verified Sep 13
    See details

    At Calvert Library - Southern Branch, teens can help shape the library experience through the TACOS Teen Advisory Council of Students. This group meets once a month to share ideas that support event planning and services for teens. Participants earn one Service Learning hour for each meeting they attend. Calvert Library is committed to making programs accessible for everyone. For accessibility questions or requests, call 410-535-0291.

    Event website ↗
  • 6pm

    Team Trivia

    Breton Bay Golf & Country Club, 21935 Society Hill Rd, Leonardtown · verified Sep 13
    See details

    A fun evening of trivia takes place every other Thursday.

    Event website ↗
  • 6:30pm

    Reading Buddies

    Calvert Library - Southern Branch, Solomons · verified Sep 13
    See details

    At Calvert Library - Southern Branch, elementary students in grades K to 5 can build confidence by reading aloud to teen volunteers and enjoying simple, engaging activities in a friendly group setting. The program nurtures a love of books, encourages social interaction between young readers and teens, and supports positive, supportive connections. Teen participants earn one service learning hour by helping children with their reading. Calvert Library is committed to accessibility. For questions or accommodation requests, call 410-535-0291.

    Event website ↗
Friday, September 25 5 events
  • 9am

    Mechanicsville Braves 6th Annual Golf Tournament

    Breton Bay Golf & Country Club, 21935 Society Hill Rd, Leonardtown · verified Sep 13
    See details

    Spend a day on the course while supporting the Mechanicsville Braves youth football and cheer club. The round uses a shotgun start. Entry is $125 per golfer and includes drinks, a meal from Scratch Mobile Kitchen, and a hot dog with a drink at the turn. On-course competitions include Longest Drive and Closest to the Pin for both men and women.

    Event website ↗
  • 9:30am

    TRX Pilates Strength & Stretch

    Vida Flow & Wellness, 41566 Medleys Neck Rd, Leonardtown · verified Sep 13
    See details

    Enjoy a TRX Pilates session that blends core engagement, mindful breathing, focus, and balance with the challenge of suspension training. Every movement is designed to strengthen and stretch while keeping you supported and in control. This full body approach targets the core, builds balance, and delivers a focused burn as you move and lengthen.

    Event website ↗
  • 1pm

    Pins and Needles

    Calvert Library, 850 Costley Way, Prince Frederick · verified Sep 13
    See details

    Bring along your quilting, needlework, knitting, crocheting, or similar project for a relaxed afternoon of friendly conversation and creative camaraderie. Library resources related to these crafts are available. For accessibility accommodations, please contact at least two weeks in advance at 410-535-0291.

    Event website ↗
  • 5:30pm

    Mercy Creek

    Northern Neck Brewing Company, 15804 Kings Hwy, Montross · verified Sep 13
    See details

    Mercy Creek brings high energy folk rock to Northern Neck Brewing Company, delivering a raw, roots-driven sound with a rugged edge. The music leans organic and gritty, pairing folk sensibilities with rock intensity.

    Event website ↗
  • 6pm

    Music Bingo

    The Barn, 16829 Kings Hwy, Montross · verified Sep 13
    See details

    Music Bingo with Dj Grim brings a lively game night to The Barn, pairing upbeat tracks with a relaxed, social vibe. Expect music, food, and plenty of fun in a friendly setting.

    Event website ↗
Saturday, September 26 8 events
  • 9am

    Lexba Market Days - September 26

    Pax River Village Center, 21703 Great Mills Rd, Lexington Park · verified Sep 15
    See details

    LEXBA Market Days at Pax River Village Center is part of a seven month effort by the Lexington Park Business Association to support local entrepreneurs and strengthen the area’s business community. This outdoor marketplace will take place regardless of weather. Produce sellers and food trucks are not part of the event. Vendors handle their own setup, including tent, tables, and chairs. Participation is $50 per month with flexible, month to month registration, and the option to take part in one month or all seven. Vendor spaces are currently open.

    Event website ↗
  • 11am

    Washington Parish Museum

    St. Peter's Episcopal Church, 2961 Kings Hwy, Colonial Beach · verified Sep 15
    See details

    Explore the Washington Parish Museum at St. Peter’s Episcopal Church in Oak Grove, Virginia. Graphic displays and historical artifacts trace more than 175 years of Episcopal Church heritage, spotlighting the Northern Neck churches that belong to Washington Parish from the colonial period through the present.

    Event website ↗
  • 12pm

    Cork for Cuties

    Action Lounge and Billiards, 25470 Point Lookout Rd, Leonardtown · verified Sep 13
    See details

    Cork for Cuties is a benefit tournament at Action Lounge and Billiards, with all proceeds going to the Clements Cuties Foundation. The lineup features sign ups, open singles in 501 and cricket, women’s singles in 501 and cricket, and an LOD 501/Cricket/CC session. Entry is $15 per event. Bring good vibes and show support for the Cuties.

    Event website ↗
  • 2pm

    On Pins and Needles (SO)

    Calvert Library - Southern Branch, Solomons · verified Sep 13
    See details

    On Pins and Needles at Calvert Library - Southern Branch brings together knitters, embroiderers, and crocheters of all levels to learn, practice, and create. Work on an in-progress piece or begin something new. A sign up is requested. Please bring your own yarn. Calvert Library works to ensure programs are accessible to everyone. For accessibility questions or requests, call 410-535-0291.

    Event website ↗
  • 6pm

    Bday Bash with RyCop

    Southern Trail Distillery, 27227 Morganza Turner Rd, Mechanicsville · verified Sep 13
    See details

    RyCop’s birthday is marked with a live band celebration at Southern Trail Distillery. The music leans toward immersive, feel-good vibes rather than hard-rock intensity, creating a lively atmosphere for a festive bash.

    Event website ↗
  • 6pm

    After Five Funhouse is back

    The Barn, 16829 Kings Hwy, Montross · verified Sep 13
    See details

    After Five Funhouse returns to The Barn with an evening of music, food, and plenty of fun. The casual setting keeps the focus on simple pleasures, from the sounds to the food.

    Event website ↗
  • 7pm

    13th Annual Scholarship Benefit Dance

    Mechanicsville Volunteer Fire Department Auxiliary, 28165 Hills Club Rd, Mechanicsville · verified Sep 13
    See details

    A benefit dance in its 13th year, dedicated to scholarships. Held at the Mechanicsville Volunteer Fire Department Auxiliary, it brings people together in support of education. For more details, please refer to the event flyer.

    Event website ↗
  • 8pm

    Taboo

    Buckets Bar & Grill, Lusby · verified Sep 13
    See details

    Experience a variety party band that plays the music you want to hear, blending Top 40, classic rock, modern rock, pop, funk, rap, hip hop, and a little country for a lively, feel-good show.

    Event website ↗
Sunday, September 27 1 event
  • 8am

    Smiles For Miles - Sunday Run Club

    Patuxent Plaza, 13962 Solomons Island Rd S, Solomons · verified Sep 13
    See details

    The group meets in the parking lot at The Beanery or Juice Buzz to set off on an easy loop of about 3 to 4 miles. It is welcoming for newcomers, keeping a relaxed 14 to 15 minute pace with one minute intervals of walking and running so everyone can take part comfortably. Participants may run, walk, or jog, or simply stop by for the friendly atmosphere. After the loop, enjoy a treat at The Beanery or Juice Buzz. The aim is simple... move, spend time outdoors, and share good company to start the day. This gathering goes on rain or shine unless conditions are unsafe.

    Event website ↗
Tuesday, September 29 1 event
  • 6pm

    Pokémon Club - Trading Card Game

    Calvert Library, 850 Costley Way, Prince Frederick · verified Sep 13
    See details

    At Calvert Library, this club offers young Pokémon enthusiasts a friendly setting to learn and get better at the Pokémon Trading Card Game while tapping into creativity with themed activities. Through play, participants build strategy, math abilities, and reading skills. Friendly battles and the fun of collecting cards promote teamwork and imagination. Aimed at tweens ages 8 to 12, the program supports confidence, skill building, and new friendships among fellow fans. For questions about accessibility or to request accommodations, call 410-535-0291.

    Event website ↗
Wednesday, September 30 2 events
  • 6pm

    Retirement Income Planning Seminar

    Cedar Point Federal Credit Union Headquarters, Lexington Park · verified Sep 13
    Free

    Learn about retirement income planning at this free, interactive seminar led by Colleen S. Blundell, vice president of investment and business services. The session invites participants to reflect on what retirement looks like for them, when they plan to stop working, and how long their resources may need to last, with additional discussion beyond these core questions. It is open to the public. Registration is required because space is limited.

    Event website ↗
  • 6:30pm

    Reading Buddies (PF) - Young Reader

    Calvert Library, 850 Costley Way, Prince Frederick · verified Sep 13
    See details

    Elementary-aged children will enjoy fun activities and read out loud to teen volunteers in a safe and welcoming space. The program is designed for K through 5th grade readers who love sharing stories or want extra practice to build confidence. Teen volunteers can earn one service learning hour for participating. For accessibility accommodations, please contact at least two weeks in advance at 410-535-0291.

    Event website ↗
Thursday, October 1 2 events
  • 6pm

    Awful Artworks (PF)

    Calvert Library, 850 Costley Way, Prince Frederick · verified Sep 13
    See details

    Set aside perfection and enjoy a relaxed art-making session at Calvert Library. Create freely without pressure about the final result. Each artwork will be labeled with its title, the artist’s name, and a brief description, and there is an option for pieces to be displayed in the library. Calvert Library is committed to accessibility for all participants. For questions or accommodation requests, call 410-535-0291.

    Event website ↗
  • 7:30pm

    Music Trivia

    Taphouse 1637, 23418 Three Notch Rd, California · verified Sep 13
    See details

    Monthly music trivia returns on the first Thursday of each month. Enjoy a fun, music-filled night that is perfect for spending time with friends.

    Event website ↗
Friday, October 2 3 events
  • 10am

    The Old Jail Museum Open for Leonardtown First Fridays

    The Old Jail Museum & Leonardtown Visitor Center, 41625 Courthouse Dr, Leonardtown · verified Sep 13
    Free

    Explore the Old Jail Museum, a landmark in the heart of Leonardtown, open with extended hours in conjunction with Leonardtown First Fridays. Enjoy a free tour of this historic site while taking in the First Friday atmosphere that evening. Staff will be present to highlight the Old Jail and share its story. The building also serves as the official Leonardtown Visitor Center, offering information and literature on area attractions, activities, dining, events, and more. A museum store features local products, books, apparel, and items for kids. Admission is free for all ages, and entry is walk-up only.

    Event website ↗
  • 5pm

    2026 First Friday Audience Participation Drum Circle

    St. Mary's County Arts Council, 22660 Washington St, Leonardtown · verified Sep 13
    Free

    First Fridays bring a community drum circle where everyone is welcome to make music together. These free gatherings invite participants of all ages and experience levels to bring a percussion instrument or use one that is provided. The session takes place on the lawn beside the St. Mary's County Arts Council office, with an indoor option if rain or excessive heat moves in. Stay for the entire program or drop in when you can. In May and October, the drum circle is followed by a drumline performance. Hosted by the St. Mary's County Arts Council, led by the SoMar Drummers, and sponsored by Nick Stellway, CCIM, of Hyatt Commercial.

    Event website ↗
  • 5:30pm

    2026 First Friday Drumline

    St. Mary's County Arts Council Gallery & Gift Shop, 22660 Washington St, Leonardtown · verified Sep 13
    Free

    Celebrate First Friday with a free youth drumline event set on the grassy area beside the office near the Leonardtown Arts Center building. Seating is limited, so bring a blanket or a chair. In the event of rain, the performance will be canceled and an announcement will be made. Supported by St. Mary's County Arts Council and the SoMar Drummers, with sponsorship from Nick Stellway, CCIM, of Hyatt Commercial. Photos by Jenn Dorsey.

    Event website ↗
Saturday, October 3 6 events
  • 8am

    Discover Scuba Diving – Try Scuba Experience

    College of Southern MD-Leonardtown, Leonardtown · verified Sep 13
    See details

    Get a first look at scuba in a guided pool session at the Wellness and Aquatic Center on the College of Southern Maryland Leonardtown campus. This introductory experience is designed for anyone trying scuba for the first time, with no certification or prior training required. Under the direct supervision of a professional instructor, you will learn the basics of equipment, breathing techniques, and safety, then practice in shallow water to get comfortable moving and breathing underwater in a safe, controlled setting. This is not a certification course, it is a relaxed, hands-on way to see what scuba feels like without tests or pressure. All necessary scuba gear is provided for use during the session and an instructor is with you the entire time. It is a good fit for first-time divers, people considering certification, or anyone seeking a unique experience. A basic level of comfort in the water is all that is needed. Minimum age is 10 years old. Spots can be reserved online, in person, or by phone.

    Event website ↗
  • 9am

    First Saturday of the Month Market Series

    Town Market, 22675 Washington St, Leonardtown · verified Sep 13
    See details

    Happening on the first Saturday of the month, this market brings together a variety of crafters along with apparel, tumblers, and desserts to shop. Look for vendors including Bee-You-Tiful Bakes, JC's Kitchen, The Glided Whisk, Morning Star Bakery, and Sweet Tea & 3D Prints.

    Event website ↗
  • 11am

    Autumn Palette: Foliage & Texture

    Two Rivers Arts, 16380 Kings Hwy, Montross · verified Sep 13
    See details

    Explore the rich palette of fall in a welcoming embroidery class led by certified botanical artist Anne McCahill. Designed for beginners and open to adults and teens, this relaxed three hour session highlights texture, color, and playful creativity. Participants will learn and practice the French knot to portray the shifting tones of autumn foliage, including reds, browns, yellows, and warm oranges. The project invites experimentation and personal expression while helping build confidence with a time honored embroidery stitch.

    Event website ↗
  • 12pm

    Josh Grigsby and County Line

    Courthouse Square, 14683 Kings Hwy, Montross · verified Sep 15
    Free

    The Montross Fall Festival on the courthouse square features toe tapping fun with Josh Grigsby and County Line. Guests may bring a chair or blanket, or find a seat on a hay bale, and stay afterward for the parade.

    Event website ↗
  • 4pm

    Calvert County Fair Livestock Auction

    Calvert County Fairgrounds, 140 Calvert Fair Dr, Prince Frederick · verified Sep 13
    See details

    This livestock auction focuses on supporting young people and investing in their future. Registration takes place before bidding, followed by the auction itself. Buyers can make a positive impact through their bids.

    Event website ↗
  • 8pm

    The Basement Snakes

    Buckets Bar & Grill, Lusby · verified Sep 13
    See details

    Experience live local music featuring The Basement Snakes.

    Event website ↗
Sunday, October 4 4 events
  • 7:30am

    The Flutter Fest 5k, Wellness Walk, & Fun Run

    John V. Baggett Park At Laurel Grove, 26929 Three Notch Rd, Mechanicsville · verified Sep 13
    See details

    The first Flutter Fest brings a timed 5K alongside a fun run and walk to John V. Baggett Park, inviting participants to move for mental wellness in Southern Maryland. Funds raised support efforts to expand access to care by easing cost barriers. The Butterfly Effect Project Inc. focuses on helping people facing financial strain, limited insurance, or other obstacles find a welcoming place to begin healing and make meaningful progress. Runners and walkers can choose the timed 5K or a non-timed option. Shirt sizes are guaranteed for early registrants, and pricing increases in tiers as the event approaches, with no race day registration.

    Event website ↗
  • 10am

    Cars & Coffee Car Show

    Town Market LLC, 22675 Washington St, Leonardtown · verified Sep 13
    See details

    Spend a laid back day with friends at a Cars & Coffee car show featuring plenty of standout vehicles to admire. Enjoy a 50/50 raffle, door prizes, cornhole, and music throughout the event. Vendor opportunities are available by direct message, and each space measures 10 by 10.

    Event website ↗
  • 11am

    Calvert County Fair

    Calvert County Fair, 140 Calvert Fair Dr, Prince Frederick · verified Sep 13
    See details

    Enjoy live music in the main pavilion at the Calvert County Fair, with gospel by The Unclouded Day followed by secular music from Chesapeake Railway. Access to these performances is included with paid admission to the fair.

    Event website ↗
  • 1pm

    Pages in the Park

    Port of Leonardtown Park & Kayak Launch, 23190 Newtowne Neck Rd, Leonardtown · verified Sep 13
    Free

    Pages in the Park offers a calm, drop-in reading time at Port of Leonardtown Park & Kayak Launch, presented in partnership with the Mobile Library. Families and readers of all ages can bring a favorite book and enjoy a quiet hour reading together in the open air. Bring a blanket or chairs, pack a few snacks, and settle into a comfortable spot to savor the shared experience of stories in the park.

    Event website ↗
Wednesday, October 7 1 event
  • 10am

    WOW (Work on Whatever) Wednesday (PF)

    Calvert Library, 850 Costley Way, Prince Frederick · verified Sep 13
    See details

    Bring whatever you are working on along with the materials you need. Paper crafting, scrapbooking, quilting, origami, and other projects are all welcome. Stay for the full gathering or drop in for a couple of hours. Use this time to make progress and connect with others. Registration is optional, and if you choose to register you will receive a reminder. For accessibility accommodations, please get in touch at least two weeks in advance at 410-535-0291.

    Event website ↗
Thursday, October 8 1 event
  • 9am

    Clydesdale Farm Barn Party

    Suttler Post Farm Clydesdale's, 38750 Chaptico Rd, Mechanicsville · verified Sep 13
    See details

    Harvest Hosts and FindUsCamping team up for the first time at Suttler Post Farm for the fifth annual FindUsCamping Campout, creating a special gathering for the RV community. Look forward to music in the barn, time with fellow travelers, and the impressive Clydesdales, all blended with the familiar charm of Harvest Hosts, the camaraderie of Escapees, and the lively spirit of FindUsCamping. Attendance is limited to Harvest Hosts and Escapees RV Club members. This is a dry camping event, and rigs must be fully contained.

    Event website ↗
Saturday, October 10 3 events
  • 9am

    Monster Market

    13470 Dowell Road, United States · verified Sep 13
    Free

    Step into a playful celebration of the odd and spooky at Annmarie’s Monster Market. Explore aisles of handmade creations, seasonal bites, and unique Halloween finds suited for all ages. Browse artisan booths filled with curious crafts and one-of-a-kind goodies, then grab refreshments from food and drink vendors, including food trucks. Entry to the market area is free. Well-behaved pets on leashes are welcome. Smoking and vaping are not permitted.

    Event website ↗
  • 9am

    5th Annual Great Mills Road Community Cleanup

    Church of the Ascension, 21641 Great Mills Rd, Lexington Park · verified Sep 15
    Free

    St. Mary's CDC leads the fifth annual community cleanup focused on Great Mills Road and the surrounding Lexington Park area. Volunteers work together to make the community cleaner and support a shared vision for a thriving Lexington Park. The first 100 volunteers receive a free T-shirt as a thank you. Lexington Park residents are encouraged to clean their own neighborhoods, and registration is requested to receive a free shirt, cleanup supplies, and to help get their neighborhood involved.

    Event website ↗
  • 10am

    Batty for Bats: Decorate Your Own Bat Box (Second Saturdays)

    Piney Point Lighthouse Museum & Historic Park, 44720 Lighthouse Rd, Piney Point · verified Sep 13
    See details

    At Piney Point Lighthouse Museum, this hands-on program introduces local bat species and the important role they play in keeping insect populations in check. Participants can personalize a bat box to help provide roosting habitat, while learning about the challenges bats face from habitat loss and disease, along with simple conservation steps that support their recovery. A bat box is reserved for the first 20 attendees, and additional guests can enjoy alternate craft activities. All ages are welcome. Admission is free, and optional donations support museum programs. For questions, email Olivia.Flack@StMarysCountyMD.gov.

    Event website ↗
Monday, October 12 1 event
  • 6pm

    SMAWL Low Cost Vaccination Clinic

    St. Mary's County Fairgrounds, 42455 Fairgrounds Road, Leonardtown · verified Sep 13
    See details

    Keep your pet protected at SMAWL's low-cost, drive-through vaccination clinic at St. Mary's County Fairgrounds. Services include rabies vaccines for $15, distemper vaccines for $15, and microchipping for $30. Visitors are served in the order they arrive, and all animals must be restrained or in carriers. Distemper vaccines are valid for one year from the date of vaccination. For rabies, a current, up-to-date rabies certificate is required to receive a three-year vaccine, otherwise the vaccine is valid for one year. You must present the certificate to verify a three-year vaccine, with no exceptions. Owners are responsible for keeping vaccination certificates safe, and SMAWL is not responsible for lost certificates. This clinic is offered monthly from March through November.

    Event website ↗
Tuesday, October 13 2 events
  • 3:30pm

    Mobile Library Stop

    Piney Point Lighthouse Museum and Historic Park, 44720 Lighthouse Rd, Piney Point · verified Sep 13
    Free

    St. Mary’s County’s Mobile Library will visit Piney Point Lighthouse Museum on certain days each month, bringing library services right to the site. Visitors can connect to Wi-Fi, sign up for or manage a library card, pick up take-home craft kits, and check out materials from the vehicle. Although holds cannot be placed on the mobile collection, staff can assist with requests for books and other materials from other library locations. Returns from any library location are accepted at this stop, and items borrowed from the vehicle may be returned to any library location. For more information, contact info@stmalib.org.

    Event website ↗
  • 5:30pm

    FREE 6 Week Cessation Class offered through the St. Mary's County Health Departmen

    St. Mary's County Health Department, 21580 Peabody St, Leonardtown · verified Sep 13
    Free

    A free, six week Nicotine Cessation Program offers weekly 45 to 60 minute sessions focused on helping participants quit using products that contain nicotine. The class covers behavioral modifications, stress management, and other techniques for reducing dependence on cigarettes, cigars, dip, and electronic smoking devices. SMCHD and Medstar St. Mary’s Hospital Office of Population and Community Health also offer a one time comprehensive session, and attending that standalone class is encouraged before enrolling in the six week program.

    Event website ↗
Wednesday, October 14 2 events
  • 3pm

    Alzheimer's Caregivers Support (SO)

    Calvert Library - Southern Branch, 13920 H G Trueman Rd, Solomons · verified Sep 13
    See details

    Caregivers supporting someone with Alzheimer’s can connect at Calvert Library - Southern Branch for a welcoming conversation focused on sharing practical tips and mutual encouragement. The session is led by Charles Harrell and Dennis Poremski of the Alzheimer’s Association. Calvert Library works to ensure events are accessible to all. For questions or requests related to access, call 410-535-0291.

    Event website ↗
  • 6pm

    Tarot Study Group: Drop-In Program (SO)

    Calvert Library - Southern Branch, 13920 H G Trueman Rd, Solomons · verified Sep 13
    See details

    Explore tarot as a creative practice for reflection, meditation, and thoughtful inquiry, or simply as an enjoyable hobby, at Calvert Library, Southern Branch. This monthly study group welcomes every experience level, from first-time readers to longtime enthusiasts, and invites participants to examine card meanings, try a variety of spreads, and learn from one another. Bring your own deck or borrow one available at the program. Registration is requested.

    Event website ↗
Saturday, October 17 6 events
  • 4:45am

    Annual Craft Fair

    27639 Moose Ln, Mechanicsville · verified Sep 13
    See details

    Explore a bustling craft marketplace in beautiful Lunenburg, Nova Scotia, where talented makers, great food, and live music come together. More than 150 vendors will be spread across multiple buildings, with an additional building added this year, and outdoor tents extending the experience. Browse a wide range of handmade work from Nova Scotian artisans, including pottery, woodworking, glass pieces, textiles, home décor, and jewelry. Food trucks will be on site both days, serving local flavors from baked treats and fudge to nuts, specialty foods, beverages, and local wines. Admission includes a weekend pass bracelet, making it easy to return. Please note that only service dogs are permitted inside buildings. Cash is recommended for smooth purchases. For more information, contact Sabcreationkey50@gmail.com.

    Event website ↗
  • 7am

    CalvertHealth Breast Cancer 5K and Fun Walk

    Solomons Medical Center, 14090 H G Trueman Rd, Solomons · verified Sep 13
    See details

    The CalvertHealth Breast Cancer 5K Walk/Run raises funds for the Sheldon E. Goldberg Center for Breast Care, helping keep specialized breast cancer services accessible in Calvert County. The event features a 5K that can be walked or run, with tiered registration options at $40 per person for early bird, $50 for standard, and $60 for day-of sign up. Personalized tribute signs are available for $50, allowing someone to be honored by name along the course. Thanks to sponsor Seven Lands and Seas Travel, each registration is entered for a chance to win a Viking Cruise valued up to $10,000. Participants must be 18 or older to win, and winners do not need to be present. Sponsorship opportunities are also offered and include benefits.

    Event website ↗
  • 9:30am

    Storytime in the Park

    Port of Leonardtown Park & Kayak Launch, 23190 Newtowne Neck Rd, Leonardtown · verified Sep 13
    See details

    Enjoy a laid-back, come-and-go reading hour created in partnership with the Mobile Library. Families and readers of every age can bring a favorite book, spread a blanket or set up chairs, and spend quiet time reading side by side in the fresh air. Snacks are welcome, and the focus is simple... sharing the calm and connection that comes from reading together in a peaceful park setting.

    Event website ↗
  • 10am

    2026 Winter Coat & Winter Clothing Giveaway Event

    Oak Grove Baptist Church Family Life Center Gym, 8044 Leedstown Rd, Colonial Beach · verified Sep 13
    Free

    Oak Grove Community Closet presents a free giveaway of winter coats, warm clothing, shoes, and essential cold weather gear at Oak Grove Baptist Church. Registration is required in advance to support an orderly experience, and families with scheduled time slots will be served first. Friendly volunteers will be available to help. Since all items come from donations, sizes, quantities, and specific selections cannot be guaranteed and are available while supplies last. Shopping bags will be provided, so personal bags are not needed. The event focuses on serving individuals and families in King George, Westmoreland, Essex, and Richmond counties, reflecting a community spirit to recycle, refresh, and re bless.

    Event website ↗
  • 11am

    calvert county bluegrass and acoustic festival

    Waters Memorial United Methodist Church, 5400 Mackall Rd, Saint Leonard · verified Sep 13
    Free

    Enjoy live bluegrass and acoustic music at Waters Memorial United Methodist Church. This festival showcases leading local and regional bands and puts the spotlight on community talent. Admission is free with a donation to the sponsored charity.

    Event website ↗
  • 8pm

    Jackson Perkins

    The Rex Theatre, 22695 Washington St, Leonardtown · verified Sep 13
    See details

    Jackson Perkins takes the stage at the Rex Theatre for an intimate country performance. An active-duty U.S. Marine, he is earning attention for a commanding vocal presence, sincere songwriting, and a deep love of classic country. Recent appearances, including performing alongside Riley Green, have introduced his music to audiences nationwide. The show offers a close-up experience with an up-and-coming artist early in his journey.

    Event website ↗
Monday, October 19 1 event
  • 12pm

    4th Annual Colonial Beach Restaurant Week

    Colonial Beach Chamber of Commerce, 201 N Irving Ave, Colonial Beach · verified Sep 13
    See details

    Experience a week of coastal flavor in Colonial Beach as creative kitchens pair their menus with riverfront charm for a true destination dining experience. Local chefs present limited-time specials featuring seafood fresh from the water, seasonal farm-sourced dishes, inventive cocktails, and indulgent desserts. Explore an eclectic mix of restaurants, intimate cafes, and scenic patios, sampling something new at each stop. Share favorite dishes, drinks, and views with the hashtag #TasteTheTidesCB to be eligible for giveaways throughout the week. Many visitors turn it into a getaway, with inns, bed and breakfasts, and cozy cottages providing relaxing places to unwind between tastings. Stroll the boardwalk, watch sunsets over the Potomac, and enjoy small town hospitality one bite at a time. Featured participants include Circa 1892, Colonial Beach Brewing, Colonial Buzz Coffee and Espresso Bar, Dockside Restaurant & Tike Bar, Drift Seafood + Bar, El Toro Authentic Mexican Food, GrandPa Hawaii Shave Ice, Guacamole II, High Tides on the Potomac & Black Pearl Tiki Bar, Ice House Brewery, Ledo Pizza, Lenny's Restaurant, Los Hermanos Cantina, Margarita Restaurant, Muse Pizzeria & Arcade, Orchid Thai Cuisine, Ola's Country Kitchen, Pier 909, Pink Poodle, and Raven's Point.

    Event website ↗
Thursday, October 22 1 event
  • 5:30pm

    GKES Trunk or Treat

    45711 Military Ln, Great Mills · verified Sep 13
    See details

    A family-friendly Trunk or Treat at GKES features a safe evening with treats, food, and spooky fun. Participants can decorate a vehicle trunk for the festivities, and sign-up is available.

    Event website ↗
Saturday, October 24 8 events
  • 10am

    Halloween in the Garden

    13470 Dowell Road, United States · verified Sep 13
    See details

    Celebrate Halloween in the garden with costumes, trick-or-treating, games, and family fun, featuring over 50 community booths set along the paths. A DJ dance party and music add to the atmosphere, with photo opportunities plus food and drinks available while exploring the spooky activities. Tickets must be reserved in advance. Members receive free admission with an advance reservation, otherwise admission is $5 at the gate if not sold out. Non-members are $5 per person in advance, or $8 at the gate if not sold out. Reduced-price admission is available for SNAP card holders by calling (410)326-4640 to arrange.

    Event website ↗
  • 11am

    12th Annual Fall Festival and Golf Cart Parade

    Town Hill, Colonial Beach, 401 Washington Ave, Colonial Beach · verified Sep 13
    See details

    Celebrate the season at the 12th Annual Fall Festival and Golf Cart Parade on Town Hill in Colonial Beach, featuring food and craft vendors, a kids zone, arts and crafts, games, music, and other family friendly activities. The day concludes with a decorated golf cart parade sponsored by Custom Cartz, with festive carts rolling through the Point for a colorful finale. Online registration and printable forms are available for parade participants as well as food and craft vendors, and the organizers provide a full event schedule.

    Event website ↗
  • 12pm

    Trunk or Treat & Vendor Show

    Town Market LLC, 22675 Washington St, Leonardtown · verified Sep 13
    See details

    Classic cars will be set up for a Trunk or Treat, handing out candy to little ghouls, goblins, and monsters. Crafters and a food vendor will be on site, with participating vendors including Pops Shop, Sweet Tea & 3D Prints, Sippin Dirty Refreshments, and Birds Nest Boutique.

    Event website ↗
  • 12pm

    Cars & Coffee Car Show - Trunk or Treat

    22675 Washington St, Leonardtown · verified Sep 13
    See details

    Enjoy a Cars & Coffee car show with a trunk or treat theme, featuring a display of standout vehicles and a relaxed setting for spending time with friends. Explore offerings from Sippin Dirty Refreshments and Birds Nest Boutique. Vendor opportunities are available by direct message, and booth spaces measure 10x10.

    Event website ↗
  • 1pm

    Monster Mash Bash

    Leonardtown Wharf, 22510 Washington St, Leonardtown · verified Sep 13
    See details

    Monster Mash Bash offers a spirited Halloween celebration for all ages, featuring festive activities, treats, and entertainment. The atmosphere is playful and spooky in equal measure, making it a fun way to celebrate the season.

    Event website ↗
  • 5:30pm

    MVRS Annual Trunk-or-Treat in the Village

    28120 Old Flora Corner Rd, Mechanicsville · verified Sep 13
    See details

    An annual Trunk-or-Treat in the Village welcomes participants to decorate vehicle trunks and compete in a Best Decorated Trunk contest. Anyone registering a trunk is required to provide candy for their display. The organizers are also accepting candy sponsorships and donations to support the festivities. All sponsors will be acknowledged at the event and on the organizers’ Facebook page.

    Event website ↗
  • 6:30pm

    Taken to the Grave

    George Washington Birthplace National Monument, 1732 Popes Creek Rd, Colonial Beach · verified Sep 13
    Free

    Park rangers present a free, family-friendly one-hour program titled Taken to the Grave at George Washington Birthplace National Monument, held near the Washington Family Burial Ground. By lantern light, participants will explore the resting place of Washington family members and delve into stories and lingering mysteries from the past with a light touch of spookiness for all ages. The gathering point is the Washington Family Burial Ground parking lot, where staff will be available to help with parking.

    Event website ↗
  • 8pm

    Sara and The Igniters @ The Mechanicsville Moose Lodge #495

    Mechanicsville Moose Lodge #495, 27651 Moose Ln, Mechanicsville · verified Sep 13
    See details

    Sara and The Igniters bring a variety party band to Mechanicsville Moose Lodge #495, with Sara Zito as the featured performer.

    Event website ↗
Wednesday, October 28 1 event
  • 6pm

    Free Estate Planning Seminar

    Cedar Point Federal Credit Union (22745 Maple Road, Lexington Park, MD), Lexington Park · verified Sep 13
    Free

    Joann Wood of The Law Office of Joann M. Wood, LLC leads a seminar that looks beyond the usual focus on end of life and taxes to the real purpose of estate planning. The session explores the fundamentals of financial security and how to arrange for your property to be transferred according to your wishes. Through clear guidance, Wood helps participants identify their goals so they and their loved ones can begin shaping plans for the future. Registration is required.

    Event website ↗
Saturday, October 31 3 events
  • 9am

    LEXBA Market Days - October 31

    Pax River Village Center 21703 Great Mills Road, Lexington Park, MD 20653 (Located in the Aaron's parking lot facing Great Mills Road), 21703 Great Mills Rd, Lexington Park · verified Sep 13
    See details

    The Lexington Park Business Association is hosting an outdoor vendor market at Pax River Village Center as part of a seven month effort to support local entrepreneurs. This market takes place rain or shine. Produce and food trucks are not permitted. Vendors handle their own setup, including tent, table, and chairs. Registration is offered month to month with the flexibility to take part in any or all of the seven months, and the vendor fee is $50 per month. Vendor applications are currently being accepted. LEXBA works to empower and uplift the Lexington Park business community.

    Event website ↗
  • 10am

    Coffee and Conversation

    2961 Kings Hwy, Colonial Beach · verified Sep 13
    See details

    This relaxed coffee gathering takes place in the Parish House at St. Peter’s Episcopal Church. Organized by the church’s Outreach Committee, it is held when the Washington Parish Museum is also open and provides a casual space for conversation. Open to everyone.

    Event website ↗
  • 1pm

    Trunk or Treat on the Flight Line

    22156 Three Notch Rd, Lexington Park · verified Sep 13
    See details

    Celebrate Halloween at the annual Trunk or Treat on the Flight Line, a family friendly tradition for the community. Explore decorated trunks, enjoy seasonal fun, and collect treats in a museum setting. Children in costume receive free admission with a paid adult. Special event admission is $7 for adults and $4 for active duty military and seniors 55 and older.

    Event website ↗
Friday, November 6 1 event
  • 7pm

    Quarter Auction at Benedict

    Benedict Volunteer Fire Department & Rescue Squad, 18210 Hyatt Ave, Benedict · verified Sep 13
    See details

    A lively quarter auction is on the way, complete with a friendly table decorating challenge. Bring together family, coworkers, neighbors, or your group to share a table, or host one on your own. Each table seats up to eight guests, and participants are invited to choose a theme and decorate to match. Feel free to bring a charcuterie spread, a picnic-style dinner, or favorite snacks to enjoy while bidding. Paddles are prepaid during registration, and paddle numbers are selected upon arrival. Creativity is celebrated with recognition for standout tables based on decor and theme, with the award presented to the person who registered the table, even if a team helped with decorations. Six sponsored tables are available for groups seeking an exclusive space, with a sponsorship fee required. Unsponsored tables remain open for individual attendees and walk-ins. While walk-ins are welcome, signing up in advance helps with seating plans. Expect an evening of spirited bidding, tasty bites, prizes, and community connection in support of the Benedict Auxiliary.

    Event website ↗
Saturday, November 7 6 events
  • 3am

    Craft and Vendor Fair

    27600 Sonny Ln, Mechanicsville · verified Sep 13
    See details

    Explore a lively marketplace set amid the charm of Lunenburg, Nova Scotia, where artisans, local flavors, and live music create a welcoming scene. More than 150 vendors fill multiple buildings, with an extra building added for 2026. Browse handmade work from Nova Scotian makers, including pottery, woodwork, glass art, textiles, home decor, jewelry, and more. Savor a variety of treats and beverages such as baked goods, fudge, nuts, specialty foods, food truck favorites, and local wines. Food trucks are available both days, and outdoor tents extend the experience beyond the buildings. Admission includes a weekend pass bracelet. Only service dogs are allowed inside buildings, and bringing cash is recommended.

    Event website ↗
  • 9am

    First Saturday of the Month Market Series

    22675 Washington St, Leonardtown · verified Sep 13
    See details

    This market features a variety of crafters and vendors offering apparel, tumblers, and desserts. Vendors include Bee-You-Tiful Bakes, JC's Kitchen, The Glided Whisk, Morning Star Bakery, and Sippin Dirty Refreshments.

    Event website ↗
  • 9:30am

    Harry Potter Mystic Market & First Saturday of the Month

    22675 Washington St, Leonardtown · verified Sep 13
    See details

    Town Market transforms into a Hogwarts inspired marketplace with a quest to track down Horcruxes. Browse mums, pumpkins, items from crafters, apparel, tumblers, and desserts from vendors. A prize will be awarded for the best Harry Potter character costume. A scavenger hunt list will be available for participants. Attending vendors include Christina's Cookies.

    Event website ↗
  • 10am

    🐚🦈 Westmoreland State Park Fall Hike (5–7 Miles) 🦈 🐚

    145 Cliff Rd, Montross · verified Sep 13
    See details

    Explore Westmoreland State Park on a moderate group hike covering 5 to 7 miles. The route travels through wooded trails and open meadows, features Potomac River viewpoints, and includes a visit to Fossil Beach. Planned segments include Laurel Point Trail, Big Meadow Trail, Turkey Neck Trail, and the Beach Trail, with optional shoreline walking at Fossil Beach. Expect vibrant seasonal foliage, river vistas, the Horsehead Cliffs overlook, and opportunities to search for shark teeth along the beach. Leashed dogs that can maintain the group’s pace are welcome. Restrooms are available at the Visitor Center, and hikers can look for the East Coast Hikers group near that location. A Virginia State Park parking fee of $10 per vehicle applies. Cell service may be limited in parts of the park, so downloading directions in advance is recommended. The drive from Virginia Beach is approximately two and a half hours each way. Attendees are asked to RSVP and update their response if plans change. Arriving a little early helps the group gather before setting out.

    Event website ↗
  • 5:30pm

    Performing with: Jamie's Gang

    Northern Neck Brewing Company, 15804 Kings Hwy, Montross · verified Sep 13
    See details

    Northern Neck Brewing Company hosts a live performance with Jamie’s Gang. Enjoy local beer, live music, and a relaxed setting suited for spending time with friends and turning it into a night out. The focus is on local sounds and local brews for an easygoing evening.

    Event website ↗
  • 8pm

    Taboo Variety Party Band

    Lusby · verified Sep 13
    See details

    A variety party band performs a mix of favorites across Top 40, classic and modern rock, pop, funk, rap, and hip hop, with a touch of country too. The set features widely known songs that span multiple genres.

    Event website ↗
Monday, November 9 1 event
  • 6pm

    Rabies Clinic with SMAWL @ St. Mary's Fair Grounds

    St. Mary's County Fairgrounds, 42455 Fairgrounds Road, Leonardtown · verified Sep 13
    See details

    St. Mary's Animal Welfare League, in partnership with the St. Mary's County Health Department, offers a monthly low-cost clinic at St. Mary's County Fairgrounds providing rabies and distemper vaccinations and microchipping for cats and dogs. Services are available to the public. Rabies and distemper shots are $15 each, and microchipping is $30. Payment is accepted by cash, check, credit or debit card, and CashApp. To receive a three-year rabies vaccination, bring a current rabies certificate, since tags alone are not accepted. Cats should arrive in carriers and dogs must be on a leash. The clinic may be canceled or rescheduled if the Fairgrounds has a scheduling conflict.

    Event website ↗
Wednesday, November 11 1 event
  • 11am

    Jolly Holly Retreat

    Hilton Garden Inn Solomons (Dowell, MD), 13100 Dowell Rd, Dowell · verified Sep 13
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    Enjoy five creative days focused on scrapbooking and card making at Hilton Garden Inn Solomons in Dowell, Maryland. Registration is 240 dollars, with a 50 dollar nonrefundable deposit collected at sign up, and those who pay in full at registration receive an exclusive retreat gift. A limited number of day spots are available at 60 dollars per day on a first come, first served basis. Each participant is provided a dedicated six foot workspace with power access, along with themed materials, a welcome gift, door prizes, and games. The experience includes classes, demonstrations, and hands-on projects you can take home. Supplies will be on hand such as album covers, pages, paper packs, stickers, embellishments, tools, storage solutions, pens, and more. A discounted hotel rate will be announced, with fees and taxes applicable, and room types include two queens or a king bed with a sofa. Hosted by Kimberly Leatherwood. All scrapbookers and crafters are welcome.

    Event website ↗
Friday, November 13 2 events
  • 6pm

    Sip, Stroll, Shop & Discover in Downtown Colonial Beach!

    Colonial Beach, Virginia, 122 Lynnhaven Ct, Colonial Beach · verified Sep 13
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    Discover Downtown Colonial Beach during an evening that celebrates local flavors, the arts, shopping, and community spirit. Buy a beer, wine, or cocktail from participating establishments and sip as you explore unique shops, galleries, restaurants, and other businesses within the designated Sip N’ Stroll area. Browse boutiques, stop by galleries during the Art Walk, find new-to-you businesses, and enjoy the waterfront setting. Admission is free, with beverages available for purchase at participating locations. Whether meeting friends or planning a date night, this downtown experience showcases all that Downtown Colonial Beach offers while supporting local businesses.

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  • 6pm

    MVRSA Annual Public Auction

    27600 Sonny Ln, Mechanicsville · verified Sep 13
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    The MVRSA Annual Public Auction will be held at the Mechanicsville Moose Lodge and features opportunities to bid on donated items. Donations valued at $100 or more are being collected for the auction. For questions or to arrange a donation, contact Sue Wood or Linda Talton. Additional details are available on the event flyer.

    Event website ↗
Saturday, November 14 1 event
  • 10am

    Deck the Halls: A DIY Ornament Workshop (Second Saturdays)

    44720 Lighthouse Rd, Piney Point · verified Sep 13
    Free

    Piney Point Lighthouse Museum hosts a hands-on ornament workshop that welcomes creativity and holiday spirit. Participants of all ages can craft personalized decorations using a variety of materials and take their creations home, making it a fitting activity for individuals and families who want a handmade touch for their seasonal décor. Admission is free, and optional donations help sustain museum programming. For questions, email Olivia.Flack@StMarysCountyMD.gov.

    Event website ↗
Saturday, November 21 1 event
  • 10am

    OGCA Merry Market

    Oak Grove Baptist Church, 8096 Leedstown Rd, Colonial Beach · verified Sep 13
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    Registration is now open for the OGCA Merry Market. This market takes place indoors at the OGBC FLC.

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Friday, November 27 2 events
  • 10am

    Holiday Market with The Grinch & Cindy Lou Who

    Town Market LLC, 22675 Washington St, Leonardtown · verified Sep 13
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    The Holiday Market at Town Market LLC features a wide variety of vendors to help jump-start holiday shopping. Keep an eye out for Cindy Lou Who keeping the Grinch in check, and capture keepsake photos with both characters to take home. Race cars and classic cars will be on display for everyone to enjoy. Children can get creative at a craft table and take part in a children’s basket raffle. Vendor spots are available. Vendors include Morning Star Bakery, Pax Snacks Freeze Dried Candy, Pops Shop xx, Mary Kay by Renee, and Birds Nest Boutique.

    Event website ↗
  • 11am

    Letters to Santa

    22675 Washington St, Leonardtown · verified Sep 13
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    Drop off your letter to Santa at Town Market by placing it in the red mailbox marked for Letters to Santa. The North Pole Express will make stops to collect all the mail. Be sure to enclose a self-addressed, stamped envelope so you can receive a letter back from Santa.

    Event website ↗
Saturday, November 28 1 event
  • 9am

    Small Business Saturday with The Grinch & Cindy Lou Who

    Town Market LLC, 22675 Washington St, Leonardtown · verified Sep 13
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    Small Business Saturday at Town Market LLC features local crafters and vendors with woodworking pieces, candles, custom apparel, jewelry, jams, jellies, salsas, Christmas trees, wreaths, and desserts, plus a food vendor on site. Cindy Lou Who will be making sure the Grinch behaves, and guests can take home photos with both characters. Hungry after browsing? Hot dogs, chips, and drinks will be sold to benefit Mother Catherine Academy. Morning Star Bakery is among the attending vendors. Vendor spaces are available.

    Event website ↗
Saturday, December 5 4 events
  • 9am

    First Saturday of the Month Market Series

    22675 Washington St, Leonardtown · verified Sep 13
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    A monthly market held on the first Saturday brings together a variety of crafters and vendors, offering apparel, tumblers, and desserts to explore and purchase. Vendors attending include Bee-You-Tiful Bakes, JC's Kitchen, The Glided Whisk, and Morning Star Bakery.

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  • 9am

    Spirit of Christmas Market

    Calvert County Fair, 140 Calvert Fair Dr, Prince Frederick · verified Sep 13
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    A two-day Christmas market at Calvert County Fair brings together makers selling crafts, a variety of food vendors, and plenty of festive fun. Browse for gifts, enjoy tasty bites, and take in the holiday atmosphere across both days.

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  • 12pm

    40th Annual Santa's Wonderland Parade and Winter Festival

    Town Hill, Colonial Beach, 401 Washington Ave, Colonial Beach · verified Sep 13
    Free

    Celebrate a cherished seasonal tradition as the 40th Annual Santa’s Wonderland Parade and Winter Festival brings cheer to Town Hill. The day begins with a lively parade featuring floats, creatively decorated cars and golf carts, and a special appearance by Santa. Twinkling lights, Christmas trees, elves, and snowmen create a festive setting for holiday fun. Enjoy hot chocolate, decorate cookies, make holiday crafts, sit by the fire pit, and listen to Christmas music while browsing and dining at vendor tents. Children can write letters to Santa, and everyone can take a photo with him. A car show presented by the Colonial Rod Club offers free entrance when you bring a toy. This community celebration welcomes kids and the young at heart and sets a joyful tone for the season.

    Event website ↗
  • 8pm

    Justin Taylor Band

    Lusby · verified Sep 13
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    Known for high-energy live shows, the Justin Taylor Band delivers a contemporary blend of rock and country.

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