For a full listing of all concerts, performances and events, visit our Events & Entertainment page.

Live Music in Leonardtown

Enjoy a variety of musical genres in the lovely, open-air venue of the Leonardtown Square. Downtown Tunes (May 28, June 25, July 23, & August 27) features bands and artists playing jazz, country, blues and rock-and-roll. LEARN MORE.

See the popular U.S. Navy Band, The Commodores, play jazz, swing and other classic favorites on May 21, 2016! Bring a chair or blanket to sit on, or make reservations for an outdoor table at one of the town's restaurants to enjoy summer Saturday evenings listening to live, local music. Learn More.

Twilight Performance Series

On Tuesday evenings (July 12, July 19, July 26 & August 2) enjoy free concerts at the Twilight Performance Series, presented by the College of Southern Maryland. Performances are held out-doors on the Leonardtown campus. Learn More.

River Concert Series

On Summer Fridays (June 17, June 24, July 1, July 8, July 15, July 22), The Chesapeake Orchestra brings the beautiful sounds of jazz, concertos, marches and waltzes to St. Mary's College of Maryland, thanks to the River Concert Series.  Each summer, Maestro Jeffrey Silberschlag and the Chesapeake Orchestra set up on the Townhouse Green along the St. Mary's River to entertain serious music lovers and casual listeners alike. These free concerts start at 7 PM, with seating and food and art vendors opening at 5 PM. Learn More.

Lil' Margaret's Bluegrass & Old Time Music Festival

Join the fun on Goddard Farm for the 28th Annual Lil’ Margaret’s Bluegrass & Old Time Music Festival (August 11, 12, 13, 2016). With home-made country cooking, tons of live music on the stage, and plenty of pickin’ in the parking lot, there's lots to enjoy at Lil' Margaret's. Learn More.

Potomac Seafood & Jazz Festival

Relax by the water and enjoy the most unique and intimate jazz experience in Southern Maryland, the Potomac Seafood & Jazz Festival, July 9, 2016. This annual event features jazz acts and scrumptious seafood on the lawn of St. Clement's Island Museum. Tickets sell out quickly. Learn More.