Leonardtown Luau

Leonardtown Square Leonardtown, Maryland

Participating bars: SocialThe Front PorchThe RexThe Olde Town PubBruSlice HouseAntoinettes Garden Music/Entertainment is to be announced!

First Friday in Leonardtown

Leonardtown Square Leonardtown, Maryland

Explore Downtown Leonardtown on First Friday! Come enjoy dinner at one of the many local restaurants, enjoy a drink from Social Coffeehouse or Antoinette's Garden, explore Shepherd's Old Field Market, shop at one of the many local shops and art galleries, and enjoy a sweet treat from Heritage Chocolates! There will be free trolley rides […]

Free

Christmas on the Square + Annual Tree Lighting

Leonardtown Square Leonardtown, Maryland

Get the holiday festivities started in Downtown Leonardtown. Come see the beautiful tree lighted for the holiday season and enjoy other fun things going on throughout the town! Your family and friends will enjoy the holiday music, entertainment, horse and carriage rides, sleigh rides, train rides, hayrides, live nativity, petting zoo, face painting, children’s crafts, […]

Free

Veterans Day Parade

Leonardtown Square Leonardtown, Maryland

The Commissioners of St. Mary’s County and the Commissioners of Leonardtown invite the public to join the Town of Leonardtown in celebrating Veteran's Day with the largest Veteran's Day parade in Maryland! The parade steps off from St. Mary’s Ryken High School, proceeds through Town Square and is immediately followed by a Memorial Ceremony.

Free