Events & Entertainment

Upcoming Events

Leonardtown First Fridays

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

Music at the Winery

Just because it is cold outside doesn't mean you can't still have fun! Beat the winter… more

Irish Cheese & Wine Pairing

Start off your St Patrick's Day celebrations early by sampling great Irish cheeses paired with our award winning wines.

Winter Wine & Dine

Our winter wine & food pairing event is back by popular demand. Quality Street Catering will… more

Irish Cheese & Wine Pairing

Start off your St Patrick's Day celebrations early by sampling great Irish cheeses paired with our award winning wines.

Summer Camp Showcase

Find out about many local camps and activities!

Night at the Museum

Bring your friends and co-workers to hang-out and decompress at the Museum.

Music at the Winery

Just because it is cold outside doesn't mean you can't still have fun! Beat the winter… more

End of Season Oyster Roast

Enjoy all you can eat oysters during this end of season oyster roast benefiting the St. Mary's County Oyster Festival

32nd Annual Easter Egg Festival

It’s a family fun event complete with egg hunts, carnival rides, face painting, photos with the Easter Bunny and so much more!

Music at the Winery

Just because it is cold outside doesn't mean you can't still have fun! Beat the winter… more

Spring Break at Sotterley

Join Sotterley for a week of family fun during Spring Break. Each day Sotterley offers special programming.

Spring Break at Sotterley

Join Sotterley for a week of family fun during Spring Break. Each day Sotterley offers special programming.

Spring Break at Sotterley

Join Sotterley for a week of family fun during Spring Break. Each day Sotterley offers special programming.

Spring Break at Sotterley

Join Sotterley for a week of family fun during Spring Break. Each day Sotterley offers special programming.

Spring Break at Sotterley

Join Sotterley for a week of family fun during Spring Break. Each day Sotterley offers special programming.

Leonardtown First Fridays

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

Potomac River Clean-up

Volunteers come out to help clean-up areas along the river and within the park. Sign-up required. Free. 301-872-5688

Spring Break at Sotterley

Join Sotterley for a week of family fun during Spring Break. Each day Sotterley offers special programming.

Lecture: The Land They Left Behind

British historian Stuart Peachey reveals the food, drink, and society of the England that St. Mary’s settlers knew. Free.

Earth Day on the Square

Organic gardening, land/sea/bay conservation, recycling, live animals, children’s activities, nature walks, kayaking and yoga. Free.

Spring Fling Car Show

Over 300 antique & classic cars on the Square in Leonardtown. Trophies, music, shops, vendors, restaurants,… more