This weekend in Leonardtown, MD

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

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.

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.

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.

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.

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.

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.

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.

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.

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

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.

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.