Leonardtown Music Events

Music events Happening Next in Leonardtown, MD

Ugly Sweater Party at The Rex featuring In Too Deep

 The Rex Theatre 28 Nov 2025
UGLY-CHRISTMAS-SWEATER-DAY

Hope In Harmony Winter Concert Series - Noel

 Leonardtown High School 13 Dec 2025
ENTERTAINMENT

Hawthorne Heights in Leonardtown

 The Rex 20 Nov 2025
CONCERTS

St. Maries Choral Arts Home Concert Carol Sing

 First Saints Community Church 15 Dec 2025
CONCERTS

Socials Obsidian Masquerade

41655 Fenwick St, Leonardtown, MD 31 Dec 2025
PARTIES

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

 Port of Leonardtown Winery 27 Dec 2025
MUSIC