Leonardtown Live Music Events

Live Music Happening Next in Leonardtown, MD

Free Concert on the Lawn featuring Unfinished Business

 21935 Society Hill Rd , Leonardtown, MD, United States, Maryland 20650 22 Aug 2025
CONCERTS

TSC Acoustic Live at the Planetarium!

STARS To STEM, Inc. 3 Oct 2025
ENTERTAINMENT

Hot Ice Live @ Port Of Leonardtown Winery

 Port of Leonardtown Winery 6 Sep 2025
PERFORMANCES

Levi Stephens LIVE

 22845 Washington Street. Unit C, Leonardtown, MD 18 Oct 2025
MUSIC

US Oyster Festival

 St. Mary's County Fairgrounds 18 Oct 2025
FESTIVALS USD 5 TO 24

For the first time ever!!!

The Rex 18 Sep 2025
MUSIC

LHS Class of 2015 Reunion

 Port of Leonardtown Winery 13 Sep 2025
WORKSHOPS

Chesapeake Mermaid at U.S. Oyster Festival

 St. Mary's County Fairgrounds 18 Oct 2025
FESTIVALS

Stab & Gab - August 2025

 Leonardtown Library 16 Aug 2025