Leonardtown Food & Drink Events

Vendors of Southern MD

Town Market LLC 20 Sep 2025

Blessing of the Fleet 2025

Leonardtown Wharf 4 Oct 2025

Cars & Coffee Car Show

22675 Washington Street, The Bell Bldg Unit 106, Leonardtown, MD 24 Aug 2025

Small Business Saturday with The Grinch & Cindy Lou Who

Town Market LLC 29 Nov 2025

First Saturday of the Month Market Series

22675 Washington St, The Bell Bldg Unit 106, Leonardtown MD 1 Nov 2025

August 29th Glass Blowing w/McFadden Art Glass

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

Live at Port of Leonardtown Winery

Port of Leonardtown Winery 23 Aug 2025

LHS Class of 2015 Reunion

Port of Leonardtown Winery 13 Sep 2025

First Saturday of the Month Market Series

22675 Washington St, The Bell Bldg Unit 106, Leonardtown MD 4 Oct 2025

Chesapeake Mermaid at U.S. Oyster Festival

St. Mary's County Fairgrounds 18 Oct 2025

Fall Craft and Vendor Sale and Community Yard Sale

St. Mary's County Fairgrounds 27 Sep 2025

Cars & Coffee Car Show

22675 Washington Street, The Bell Bldg Unit 106, Leonardtown, MD 5 Oct 2025

(Friday event} Salsa On The Vine at The Port of Leonardtown Winery.

Port of Leonardtown Winery 19 Sep 2025

Cars & Coffee Car Show

22675 Washington Street, The Bell Bldg Unit 106, Leonardtown, MD 21 Sep 2025

Fur Babies with the Grinch and Holiday Market

22675 Washington St, The Bell Bldg Unit 106, Leonardtown MD 6 Dec 2025