Leonardtown Events

Explore Leonardtown, Maryland, through its vibrant calendar of events, offering something for everyone year-round. From lively festivals and farmers' markets to art exhibits and community gatherings, this charming town invites you to experience its rich culture and friendly atmosphere. Stay up-to-date and plan your visit to join in the fun!

Past Events

August First Friday in Leonardtown
August 1 - 3, 2025

Southern Maryland Boat Club Summer Boat Regatta
July 26 - 27, 2025

July First Friday in Leonardtown
July 4 - 6, 2025

Annual St. Mary's County Crab Festival
June 14, 2025

June First Friday in Leonardtown
June 6 - 8, 2025

RenFest Southern Maryland
May 24 - 25, 2025

Leonardtown Summer Splash Silent Disco
May 23, 2025

Southern Maryland Heritage Festival
May 17 - 18, 2025

Leonardtown Spring Fling Car Show
May 4, 2025

May First Friday in Leonardtown
May 2 - 4, 2025

April First Friday in Leonardtown
April 4, 2025

March First Friday in Leonardtown
March 7, 2025

February First Friday in Leonardtown
February 7, 2025

January First Friday in Leonardtown
January 3, 2025

December First Friday in Leonardtown
December 6, 2024

Christmas in the Leonardtown Square
November 29, 2024

Leonardtown Annual Veterans Day Parade
November 11, 2024