40th Annual St Mary's County Crab and Music Festival

St. Mary's County Fairgrounds 13 Jun 2026

RenFest Southern Maryland

Brüdergarten (Brü) 23 May 2026

St. Mary’s Freedom Fest

St. Mary’s Freedom Fest 3 Jul 2026

Federated Wrestling Alliance: Amplified

The Rex 29 May 2026

Spin It Again at RenFest Southern MD

Brudergarten Beer Garden at Shepherd’s Old Field Market 24 May 2026

Rabies Clinic with SMAWL @ St. Mary's Fair Grounds

St. Mary's County Fairgrounds 13 Jul 2026

[STELLAR SESSIONS] [A TRIBUTE TO INCUBUS] [PERFORMED BY HYDRAFX]

The Rex Theatre 27 Jun 2026

Monster Mash Bash

Leonardtown Wharf 24 Oct 2026

SUMMER SMASH

The Rex 20 Jun 2026

🇺🇸 PBR All American Mechanical Bull Night @ The Rex Theater

22695 Washington St, Leonardtown, MD, United States, Maryland 20650 6 Jun 2026

Outdoor Art & Movie Night

Town Market LLC 19 Sep 2026

DeSco Beauty Grand Opening

23976 Point Lookout Rd, Leonardtown, MD 23 May 2026

🤠 Honky Tonk Havoc @ The Rex Theater 🔥

22695 Washington St, Leonardtown, MD, United States, Maryland 20650 5 Jun 2026

40th Anniversary Flag Day Celebration

Leonard Hall Rec Center 14 Jun 2026

Diamonds in the Rough

21935 Society Hill Rd , Leonardtown, MD, United States, Maryland 20650 28 May 2026

2026 First Friday Audience Participation Drum Circle

22660 Washington St., Leonardtown, MD, United States, Maryland 20650 5 Jun 2026

16th Annual Crime Solvers Golf Tournament ⛳️

Breton Bay Golf & Country Club 25 Jun 2026

Riftbound case Tournament!

The Griffon’s Court Games & Collectibles 5 Jun 2026

Christmas In July @ The Rex Theater 🎄

22695 Washington St, Leonardtown, MD, United States, Maryland 20650 25 Jul 2026

Happy Hour Yoga

41566 Medleys Neck Road, Leonardtown, MD, United States, Maryland 20650 29 May 2026