Entertainment events in Chestertown

Check out happening entertainment events all around Chestertown, MD

The 30th Annual Chestertown Tea Party Distance Classic Race and Run for Radcliffe (5K & 10-Mile Run)

 Sat, 23 May at 08:00 am Wilmer Park

2026 Chestertown Pride Festival!

 Sat, 02 May at 01:00 pm 413 S Cross Street, 21620

Schooner SULTANA Public Sails 2026-May

 Sat, 02 May at 11:00 am Chestertown Marina USD 23 to 44

The Spongebob Musical

 Fri, 17 Apr at 07:00 pm Garfield Center for the Arts at the Prince Theatre USD 18 to 29

Saturday in the Park!

 Sat, 30 May at 12:00 pm Wilmer Park

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

 Sat, 30 May at 07:00 pm The Shanty Beach Bar at Tolchester Marina

Sultana's Annual Gala, May 9, 2026

 Sat, 09 May at 06:00 pm Clovelly Farm USD 200

Schooner SULTANA Public Sails 2026-June

 Fri, 26 Jun at 05:00 pm Chestertown Marina USD 23 to 44

Schooner SULTANA Public Sails 2026-August

 Fri, 14 Aug at 05:00 pm Chestertown Marina USD 23 to 44

Schooner SULTANA Public Sails 2026-July

 Fri, 24 Jul at 05:00 pm Chestertown Marina USD 23 to 44

Schooner SULTANA Public Sails 2026-September

 Fri, 04 Sep at 05:00 pm Chestertown Marina USD 23 to 44

Loveboat Yacht Rock at the Shanty Bar at Tolchester Marina

 Fri, 04 Sep at 01:00 pm The Shanty Beach Bar at Tolchester Marina

Movie & Arts Night: Drop-Off Studio Experience for Kids in Chestertown

 Fri, 15 May at 06:00 pm Artist Michael Bell Studio & Workshops USD 60

Grape Expectations: Brampton 1860 “Mexico Reimagined”

 Thu, 28 May at 06:00 pm 25227 Chestertown Rd USD 98

JJBB at the Shanty Beach Bar at Tolchester Marina

 Fri, 15 May at 07:00 pm The Shanty Beach Bar at Tolchester Marina

2026 Chestertown Pride Festival - All Ages Dance Party!

 Fri, 01 May at 05:00 pm 413 S Cross Street, 21620

Spongebob Squarepants the Musical - Chestertown

 Sat, 25 Apr at 11:00 pm Garfield Center for the Arts at the Prince Theatre

Memorial Day Jam at the Sandbar

 Mon, 25 May at 03:00 pm ROLPHS WHARF MARINA

Summer Launch Party

 Sat, 30 May at 12:00 pm 302 Park Row, Chestertown, MD 21620-1544, United States