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 features bands and artists playing jazz, country, blues and rock-and-roll, on the fourth Saturday of the month, May - August. 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. See the line-up here of live music in Leonardtown!

Twilight Performance Series

Tuesday evenings, June 17 & 24 and July 15 & 22, enjoy free concerts at the Twilight Performance Series, presented by the College of Southern Maryland. Performances are held out-doors on the Leonardtown campus.

River Concert Series

Summer Fridays, June 20 - July 25, bring 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. See the lineup!

Lil' Margaret's Bluegrass & Old Time Music Festival

Join the fun on Goddard Farm for the 25th Annual Lil’ Margaret’s Bluegrass & Old Time Music Festival, August 8, 9 and 10. With home-made country cooking and a total of 27 hours of live music on the stage and plenty of pickin’ in the parking lot, there's plenty to enjoy at Lil' Margaret's.

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 13. This annual event features jazz acts and scrumptious seafood on the lawn of St. Clement's Island Museum.  Tickets go on sale June 1 and sell out quickly. Learn more.

Jazz at Cafe des Artistes

Gretchen Richie, backed by the Jazz Cabaret quartet, serenades the patrons of Cafe des Artistes restaurant in Leonardtown with smooth, romantic jazz and popular music. See the performance line up. Randy Richie performs each Friday and Saturday night, playing classic and popular pieces on the piano. Dining reservations are recommended.