Festivals in Chestertown

Check out happening festivals events all around Chestertown, MD

Legacy Day 2025

 Fri, 15 Aug at 06:00 pm Chestertown, Md 21620

Grape Expectations: A Playful Plates Party at Brampton 1860, Gourmet Picnic

 Thu, 21 Aug at 06:00 pm 25227 Chestertown Rd USD 75

Kent AG Center Dog Days featuring Delmarva DockDogs

 Sat, 13 Sep at 07:30 am Kent County Fair / Kent Ag Center

2025 Chestertown Jazz Festival

 Sat, 06 Sep at 12:00 pm Wilmer Park USD 45

Sultana's Downrigging-Festival Village Passes-2025

 Fri, 31 Oct at 03:00 pm Chestertown Marina USD 28 to 55

"Rhythm-N-Vines"

 Sat, 06 Sep at 01:00 pm 9155 American Legion Rd USD 29 to 55

Downrigging Weekend Sails--Friday, October 31, 2:30pm-5:00pm

 Fri, 31 Oct at 02:30 pm Chestertown Marina USD 49 to 71

Chesapeake Bound - Book Signing @The Bookplate, Chestertown, MD

 Sat, 01 Nov at 03:00 pm The Bookplate

Downrigging Weekend Sails--Saturday Afternoon, Nov. 1, 2:30pm-5:00pm

 Sat, 01 Nov at 02:30 pm Chestertown Marina USD 40 to 71

Downrigging Weekend Sails--Sunday, Nov. 2, 1:00pm-3:30pm

 Sun, 02 Nov at 01:00 pm Chestertown Marina USD 44 to 71

Schooner SULTANA Public Sails 2025-September

 Sat, 13 Sep at 11:00 am Chestertown Marina USD 23 to 44