Happening Next

Chestertown Live Music Events

Live Music Happening Next in Chestertown, MD

30th & Final Chestertown Jazz Festival

 Wilmer Park 12 Sep 2026
FITNESS USD 45

2026 Sultana Downrigging Festival Music Village Passes

 Chestertown Marina 30 Oct 2026
FITNESS USD 28 TO 55

Loveboat Yacht Rock at the Shanty Bar at Tolchester Marina

 The Shanty Beach Bar at Tolchester Marina 4 Sep 2026
ENTERTAINMENT

Bi-Monthly Bluegrass Jam

 Lawrence Wetlands Preserve 19 Sep 2026
FITNESS FREE