Events & Entertainment

Upcoming Events

Twilight Performance Series

Enjoy free, live music at The College of Southern Maryland Leonardtown Campus

Breakfast with the Animals

Enjoy a light breakfast, a story, and an opportunity to help feed the Plantation livestock. Designed… more

Leonardtown First Fridays

The First Friday of each month, historic Leonardtown retailers open their doors to showcase live music,… more

The Sotterley Farmer’s Market

For the second year running, Sotterley continues their over 300 year farming tradition with the Sotterley… more

Beach Party on the Square

Fun in the Sun! Sand volleyball, fire truck hose downs, paddleboards, live music, food and contests. Free.

War On Wheels I, II, III

Insane Heads-Up action! Featuring outlaw pro mods! Last man/women standing in insane heads-up action.

Sunrise Yoga on the Wharf

Greet the day at the beautiful and picturesque Leonardtown Wharf Park with serenity and a good… more

The Sotterley Farmer’s Market

For the second year running, Sotterley continues their over 300 year farming tradition with the Sotterley… more

Coastal Arts Market

The Coastal Arts Market is an outdoor monthly market held the Third Saturday of every month… more

Children’s Day

Children's games, entertainment, and activities for the whole family. Food, music, and boat rides free for kids. Free.