Best events in

Leonardtown

Events and things to do in Leonardtown, MD offer a lively, locally-focused experience. As Southern Maryland's only designated Arts & Entertainment District, the scene is concentrated in its walkable historic Town Square. The social rhythm often flows from afternoon winery music to evening shows at intimate venues.

• An evening out can easily flow from drinks at a place like Antoinette's Garden or Social Coffeehouse to a show at The Rex, all within the walkable downtown.
• The Port of Leonardtown Winery provides a different pace with weekend afternoon music and creative workshops in a scenic park setting.
• Shepherd's Old Field Market serves as a community hub, where visitors can explore unique shops before settling in for weekly trivia or karaoke at Brudergarten Beer Garden.