Chestertown Live Music Events

Live Music Happening Next in Chestertown, MD

2026 Chestertown Pride Festival!

 413 S Cross Street, 21620 2 May 2026
FESTIVALS

The Spongebob Musical

 Garfield Center for the Arts at the Prince Theatre 17 Apr 2026
LIVE-MUSIC USD 18 TO 29

Saturday in the Park!

 Wilmer Park 30 May 2026
KIDS

LHM debuts @ The Shanty Beach Bar at Tolchester Marina! (Chestertown, MD)

 The Shanty Beach Bar at Tolchester Marina 30 May 2026
ENTERTAINMENT

Sultana's Annual Gala, May 9, 2026

 Clovelly Farm 9 May 2026
NONPROFIT USD 200

Loveboat Yacht Rock at the Shanty Bar at Tolchester Marina

 The Shanty Beach Bar at Tolchester Marina 4 Sep 2026
ENTERTAINMENT

Spongebob Squarepants the Musical - Chestertown

 Garfield Center for the Arts at the Prince Theatre 25 Apr 2026
LIVE-MUSIC

The High and Wides with Caleb Stine

 Garfield Center for the Arts at the Prince Theatre 8 May 2026
MUSIC USD 29

Bi-Monthly Bluegrass Jam

 Lawrence Wetlands Preserve 7 Mar 2026
FREE