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

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

Schooner SULTANA Public Sails 2026-May

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

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-September

 Fri, 04 Sep 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