Vendor Events in Leonardtown, MD

2 farmers markets, craft fairs, festivals, and pop-ups in Leonardtown, MD. Find booth fees, open spots, and apply to sell.

Festivals in Leonardtown(2)

Leonardtown First Fridays

by Leonardtown Business Association

Leonardtown Square, 41675 Fenwick St, Leonardtown, MD 20650

First Friday of each month, May - December 2026, 5 PM - 8 PM

Festival$35/event artisan vendor

25 spots open

Monthly arts and culture evening featuring artisan vendors, live music, gallery openings, street performers, and extended shop hours throughout historic Leonardtown Square.

St. Mary's County Oyster Festival

by St. Mary's County Rotary Club

St. Mary's County Fairgrounds, 42455 Fairgrounds Road, Leonardtown, MD 20650

Third weekend of October

FestivalContact organizer

150 spots open

Home of the National Oyster Shucking Championships and National Oyster Cook-Off since 1967. Features 150+ vendors, oysters prepared every way, live music, and craft beer.

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