Leonardtown Music Events

Music events Happening Next in Leonardtown, MD

Blessing of the Fleet 2025

 Leonardtown Wharf 4 Oct 2025
FIREWORKS

2025 First Friday Drumline Events!

 22660 Washington St., Leonardtown, MD, United States, Maryland 20650 3 Oct 2025
FIRST-FRIDAY

A Top Gun Party Night!

 The Rex 27 Sep 2025
PARTIES

Redneck Rave at The Rex

 The Rex 26 Sep 2025
RAVES

Levi Stephens LIVE

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

Family Tradition Hank Jr. Tribute @ The Rex Theatre Leonardtown, Maryland

 The Rex Theatre 13 Sep 2025
MUSIC

For the first time ever!!!

The Rex 18 Sep 2025
MUSIC

Death at the Disco

 Antoinette’s Garden 19 Oct 2025
PARTIES USD 20

Sabbath @ The Rex !

 The Rex 8 Nov 2025

LHS Class of 2015 Reunion

 Port of Leonardtown Winery 13 Sep 2025
WORKSHOPS

TSC Acoustic Live at the Planetarium!

STARS To STEM, Inc. 3 Oct 2025
ENTERTAINMENT

Taylor’s Engagement Brunch at The Rex!

 The Rex 14 Sep 2025
BRUNCH

Chesapeake Mermaid at U.S. Oyster Festival

 St. Mary's County Fairgrounds 18 Oct 2025
FESTIVALS

The Basement Snakes Rock the Rex

 The Rex 25 Sep 2025
MUSIC

Spin It Again at Blessing of the Fleet

 Leonardtown Wharf Park 4 Oct 2025
FIREWORKS

US Oyster Festival

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

Cars & Coffee Car Show

 22675 Washington Street, The Bell Bldg Unit 106, Leonardtown, MD 5 Oct 2025
CAR-SHOWS

Cars & Coffee Car Show

 22675 MD-326, Leonardtown, MD 20650-3848, United States 18 Oct 2025
CAR-SHOWS

Cars & Coffee Car Show

 22675 Washington Street, The Bell Bldg Unit 106, Leonardtown, MD 21 Sep 2025
CAR-SHOWS

Cars & Coffee Car Show

 22675 Washington Street, The Bell Bldg Unit 106, Leonardtown, MD 19 Oct 2025
CAR-SHOWS

Eclipse at The Rex

 The Rex 15 Nov 2025