Leonardtown Festivals Events

St. Mary's County Fair - 2026

St Marys County Fair 24 Sep 2026

SMBC Boat Regatta the Wharf

Leonardtown Wharf 25 Jul 2026

Arts & Entertainment Celebration First Friday

Leonardtown Square 4 Sep 2026

Harry Potter Mystic Market & First Saturday of the Month

22675 Washington St, The Bell Bldg Unit 106, Leonardtown MD 7 Nov 2026

The Old Jail Museum Open for Leonardtown First Fridays (Extended Hours) (FREE)

41625 Courthouse Dr, Leonardtown, MD, United States, Maryland 20650 4 Sep 2026

2026 First Friday Drumline Events

22660 Washington St., Leonardtown, MD, United States, Maryland 20650 2 Oct 2026