Festivals in Leonardtown

Check out happening festivals events all around Leonardtown, MD

2025 First Friday Drumline Events!

 Fri, 03 Oct at 05:30 pm 22660 Washington St., Leonardtown, MD, United States, Maryland 20650

Hot Ice Live @ Port Of Leonardtown Winery

 Sat, 06 Sep at 02:00 pm Port of Leonardtown Winery

Leonardtown Local Author & Book Fair

 Sun, 14 Sep at 10:00 am The Rex

4th Annual Walk for Recovery

Sat, 20 Sep at 09:00 am Leonardtown Square

Fall Craft and Vendor Sale and Community Yard Sale

 Sat, 27 Sep at 07:00 am St. Mary's County Fairgrounds

Chesapeake Mermaid at U.S. Oyster Festival

 Sat, 18 Oct at 12:00 pm St. Mary's County Fairgrounds

Spin It Again at Blessing of the Fleet

 Sat, 04 Oct at 12:00 pm Leonardtown Wharf Park

US Oyster Festival

 Sat, 18 Oct at 10:00 am St. Mary's County Fairgrounds USD 5 to 24

Trunk or Treat & Vendor Show

 Sat, 25 Oct at 09:00 am Town Market LLC

Veteran's Day Celebration

 Tue, 11 Nov at 09:00 am Town Market LLC

Come Out and See the Grinch & Christmas Shopping Spree

 Sat, 13 Dec at 09:00 am Town Market LLC