St. Mary's County Fair - 2026

LGBTQ+ Family Ice Cream Social

Thu, 24 Sep at 03:30 pm The Salted Scoop

St. Mary's County Fair - 2026

Thu, 24 Sep at 04:00 pm St Marys County Fair

Mechanicsville Braves 6th Annual Golf Tournament

Fri, 25 Sep at 09:00 am Breton Bay Golf & Country Club

TRX Pilates Strength & Stretch

Fri, 25 Sep at 09:30 am 41566 Medleys Neck Road, Leonardtown, MD, United States, Maryland 20650

Walk w/Brandon in the St. Mary's County Fair Parade

Sat, 26 Sep at 10:00 am St. Mary's County Fairgrounds

🎯 CORK FOR CUTIES🎯

Sat, 26 Sep at 12:00 pm 25470 Point Lookout Rd Leonardtown md 20650

Meet & Greet with Hip-hop legend Judah Priest

Sat, 26 Sep at 12:00 pm 41665 Fenwick St. unit 15, Leonardtown, MD

Kelly McGinn Clinic 27 September

Sun, 27 Sep at 09:00 am 41345 Camp Maria Rd, Leonardtown, MD 20650-4220, United States, Leonardtown, MD

Leonardtown is happening.

See everything else that’s on — concerts, markets, comedy and more.

Explore Leonardtown →