Downtown Leonardtown will host a Crab Walk & Shop Crawl on Saturday, Aug. 29, starting at noon, giving visitors a self-guided day of crab-inspired food and local shopping across nearly 30 participating businesses.
The Crab Walk portion invites visitors to make their way through participating restaurants and eateries for crab-inspired bites, creative dishes and specialty drinks, with no set ending time — guests are encouraged to move at their own pace. Participating Crab Walk locations include Olde Town Pub, The Front Porch, Everyday Saint, Boones Bagels, Smash House, Social Coffeehouse, Antoinette’s Garden, Kneaded Baking Co., Rucci’s, The Rex, T&J’s Cove, The Slice House, Bruder Garten, Botanic Café and Il Piccolo Morso.
Running alongside it, the Shop Crawl encourages visitors to explore Leonardtown’s locally owned shops, boutiques, galleries and markets. Participating Shop Crawl locations include Town Market, A&D Woodcrafts, The Vintage Collective, Crafts N Stitches, New View Fiberworks, Shepherd’s Old Field Market, Marie & Nash, The Inn at Leonardtown Gift Shop, St. Mary’s Arts Council Gallery, Uptown Girl Boutique, Iron & Hyde, Knot Ordinary, Kings of Cards and SOF Market.
The event follows a format Leonardtown’s downtown business community has used for several similarly styled events throughout the year, including the Paw Crawl, a pet-focused walking event returning for its second year on Sept. 27, and a spring bar crawl held earlier in 2026. Crabs are a recurring theme in the area’s tourism calendar more broadly — Leonardtown is part of the Southern Maryland Crab & Oyster Trail, and St. Mary’s County hosts several other seafood-focused events throughout the year, including the St. Mary’s County Crab Festival and a Crab and Music Festival each June.
Organizers describe the Crab Walk & Shop Crawl as a chance to spend the day exploring historic downtown Leonardtown while supporting local businesses. No tickets or registration were mentioned in the event announcement; visitors are simply encouraged to show up, explore at their own pace, and visit as many participating locations as they’d like.
The event begins at noon Saturday, Aug. 29, in downtown Leonardtown.
