Leonardtown Food & Drink Events

Food & Drink events Happening Next in Leonardtown, MD

Vendors of Southern MD

 Town Market LLC 20 Sep 2025
SPORTS

Blessing of the Fleet 2025

 Leonardtown Wharf 4 Oct 2025
FIREWORKS

Small Business Saturday with The Grinch & Cindy Lou Who

 Town Market LLC 29 Nov 2025
SHOPPING

First Saturday of the Month Market Series

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

LHS Class of 2015 Reunion

 Port of Leonardtown Winery 13 Sep 2025
WORKSHOPS

First Saturday of the Month Market Series

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

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

The Fenwick Inn presents a Mad Hatter's Tea

 The Fenwick Inn 28 Sep 2025
PARTIES USD 50 TO 71

US Oyster Festival

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

Cars & Coffee Car Show

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

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

 Port of Leonardtown Winery 19 Sep 2025
DANCE

Ace’s Angels Breast Cancer Awareness Walk & Paint Soirée

 Leonardtown Wharf 25 Oct 2025
FOOD-DRINKS

Cars & Coffee Car Show

 22675 MD-326, Leonardtown, MD 20650-3848, United States 18 Oct 2025
CAR-SHOWS

Cars & Coffee Car Show

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

Fur Babies with the Grinch and Holiday Market

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

Fall Dinner

 Olde Breton Inn 24 Oct 2025
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