Leonardtown Festivals Events

Free Concert on the Lawn featuring Unfinished Business

21935 Society Hill Rd , Leonardtown, MD, United States, Maryland 20650 22 Aug 2025

August 29th Glass Blowing w/McFadden Art Glass

23190 Newtowne Neck Rd, Leonardtown, MD, United States, Maryland 20650 29 Aug 2025

2025 First Friday Drumline Events!

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

Hot Ice Live @ Port Of Leonardtown Winery

Port of Leonardtown Winery 6 Sep 2025

US Oyster Festival

St. Mary's County Fairgrounds 18 Oct 2025

4th Annual Walk for Recovery

Leonardtown Square 20 Sep 2025

Chesapeake Mermaid at U.S. Oyster Festival

St. Mary's County Fairgrounds 18 Oct 2025

Leonardtown Local Author & Book Fair

The Rex 14 Sep 2025

Trunk or Treat & Vendor Show

Town Market LLC 25 Oct 2025

Veteran's Day Celebration

Town Market LLC 11 Nov 2025

Come Out and See the Grinch & Christmas Shopping Spree

Town Market LLC 13 Dec 2025