Leonardtown Festivals Events

Festivals Happening Next in Leonardtown, MD

2025 First Friday Drumline Events!

 22660 Washington St., Leonardtown, MD, United States, Maryland 20650 3 Oct 2025
FIRST-FRIDAY

Leonardtown Local Author & Book Fair

 The Rex 14 Sep 2025
ART

4th Annual Walk for Recovery

Leonardtown Square 20 Sep 2025
ART

Fall Craft and Vendor Sale and Community Yard Sale

 St. Mary's County Fairgrounds 27 Sep 2025
FOOD-DRINKS

Chesapeake Mermaid at U.S. Oyster Festival

 St. Mary's County Fairgrounds 18 Oct 2025
FESTIVALS

Spin It Again at Blessing of the Fleet

 Leonardtown Wharf Park 4 Oct 2025
FIREWORKS

US Oyster Festival

 St. Mary's County Fairgrounds 18 Oct 2025
FESTIVALS USD 5 TO 24

Trunk or Treat & Vendor Show

 Town Market LLC 25 Oct 2025
TRUNK-OR-TREAT

Veteran's Day Celebration

 Town Market LLC 11 Nov 2025
PARADES

Come Out and See the Grinch & Christmas Shopping Spree

 Town Market LLC 13 Dec 2025
SHOPPING