Leonardtown Live Music Events

Live Music Happening Next in Leonardtown, MD

Rucci’s Italian Kitchen – Leonardtown Grand Opening!

 22685 Washington Street, Leonardtown, MD, United States, Maryland 20650 22 Dec 2025
MUSIC

Bob Pinnola and Rosa Hance at Port of Leonardtown Winery on December 27th, 2pm-5pm

 Port of Leonardtown Winery 27 Dec 2025
MUSIC

Pictures with Santa Clause

 Town Market LLC 20 Dec 2025
PICTURES-WITH-SANTA

Daniela Bubb Returns to Antoinette's Garden

 Antoinette's Garden 19 Dec 2025
MUSIC

🚨 WAKA FLOCKA FLAME LIVE at The Rex Theater! 🚨

 22695 Washington St, Leonardtown, MD, United States, Maryland 20650 22 Jan 2026
ART