Leonardtown Music Events

Summer Smash 2.0

The Rex 8 Aug 2026

The Joe Cox Band LIVE @ The Rex Theatre

22695 Washington St, Leonardtown, MD, United States, Maryland 20650 29 Aug 2026

Christmas In July @ The Rex Theater 🎄

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

Jason Morton & The Chesapeake Sons @ Cryer's Back Road Inn (Leonardtown, MD)

Cryer's Back Road Inn 31 Jul 2026

Friday Summer Skate

Leonard Hall Rec Center 17 Jul 2026

2026 First Friday Audience Participation Drum Circle

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

2026 First Friday Drumline Events

22660 Washington St., Leonardtown, MD, United States, Maryland 20650 2 Oct 2026

Cars & Coffee Car Show

22675 Washington Street, The Bell Bldg Unit 106, Leonardtown, MD 4 Oct 2026

Cars & Coffee Car Show

22675 Washington Street, The Bell Bldg Unit 106, Leonardtown, MD 6 Sep 2026

Cars & Coffee Car Show

22675 Washington Street, The Bell Bldg Unit 106, Leonardtown, MD 20 Sep 2026

90's Country Night by Hat Trick Band @ The Rex Theatre!

22695 Washington St, Leonardtown, MD, United States, Maryland 20650 13 Aug 2026