Family events in Leonardtown, MD

An event where a portion of every sale supports students, staff, and teachers, and helps fund events held all year long. Every purchase contributes to these efforts.

Explore art without pressure at Calvert Library in Prince Frederick. Try out ideas that might not go as planned and focus on the joy of creating rather than a perfect result. Each piece will receive a tag listing the artwork title, the artist’s name, and a brief description, and creations can be displayed in the library. Calvert Library works to ensure accessibility for everyone. For access questions or requests, call 410-535-0291.

The Old Jail Museum, a well known landmark in the heart of Leonardtown, opens with extended hours for Leonardtown First Fridays. Free walk-in tours are available, with staff on site to share the history of the Old Jail and highlight its features. The building also serves as the official Leonardtown Visitor Center, offering information and literature on local attractions, activities, dining, and events. A museum shop is available with local products, books, apparel, and items for kids. Admission is free for all ages, and visits are walk-up only.

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.

The market offers a range of goods to explore, including handmade items, apparel, custom tumblers, and a variety of desserts. Vendors attending include Bee-You-Tiful Bakes, The Glided Whisk, Morning Star Bakery, Sippin Dirty Refreshments, and Penrod’s Sweet Treats.

Town Market transforms into a Hogwarts inspired marketplace with a Horcrux quest to complete. Shoppers can explore mums, pumpkins, handmade crafts, apparel, tumblers, and desserts. A prize will be awarded for the best Harry Potter character costume. A scavenger hunt is available and participants can pick up the list on site. Vendors expected include Christina's Cookies, Destination Family, Crafty Fox, Hoodkandbookd, Penrod's Sweet Treats, The Oma Shop, Mom Bun Accessories, Lantern and Quill Bookshop, and Primal Brew. Vendor spaces are 10x10 and those interested are asked to message directly for details.

Backyard Market at The Shoppe brings a friendly showcase of local vendors to Parks Plant Shoppe, hosted by a local plant dealer. Explore handmade goods, plants, and food while browsing a varied mix of small businesses. Look for Pop N Pancakes with mini pancakes loaded with toppings, plus iced coffees and dirty sodas, along with mobile clothing boutiques, artisan jewelry, a slime creation station, 3D printed pieces, pens, keychains and wristlets, mystery book picks, crocheted items, and plenty of houseplants. Early shoppers who make a purchase inside the shop can receive a complimentary plant, with the first fifteen getting a 4 inch plant and the next fifteen receiving a 2 inch plant. Overflow parking is available directly behind the plant shop through the gate.

Celebrate Game Store Day at the Southeast Neighborhood Library with gaming sessions, special guest visits, and goodies. More details will be announced soon.