Leonardtown Live Music Events

Summer Smash 2.0

The Rex 8 Aug 2026

Arts & Entertainment Celebration First Friday

Leonardtown Square 4 Sep 2026

The Joe Cox Band LIVE @ The Rex Theatre

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

Jackson Perkins Live at the Rex Theatre

22695 Washington St, Leonardtown, MD, United States, Maryland 20650 17 Oct 2026

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

Cryer's Back Road Inn 31 Jul 2026

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

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