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