Leonardtown Festivals Events

St. Mary's County Fair - 2026

St Marys County Fair 24 Sep 2026

Blessing of the Fleet 2026

Leonardtown Wharf 3 Oct 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

Monster Mash Bash

22510 MD-326, Leonardtown, MD 20650-3898, United States 24 Oct 2026