Chestertown Festivals Events

Festivals Happening Next in Chestertown, MD

Legacy Day 2025

 Chestertown, Md 21620 15 Aug 2025
FESTIVALS

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

 25227 Chestertown Rd 21 Aug 2025
FOOD-DRINKS USD 75

Kent AG Center Dog Days featuring Delmarva DockDogs

 Kent County Fair / Kent Ag Center 13 Sep 2025
DOG

2025 Chestertown Jazz Festival

 Wilmer Park 6 Sep 2025
MUSIC USD 45

Sultana's Downrigging-Festival Village Passes-2025

 Chestertown Marina 31 Oct 2025
FESTIVALS USD 28 TO 55

"Rhythm-N-Vines"

 9155 American Legion Rd 6 Sep 2025
FESTIVALS USD 29 TO 55

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

 Chestertown Marina 1 Nov 2025
USD 40 TO 71

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

 Chestertown Marina 31 Oct 2025
USD 49 TO 71

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

 The Bookplate 1 Nov 2025
FESTIVALS

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

 Chestertown Marina 2 Nov 2025
USD 44 TO 71

Schooner SULTANA Public Sails 2025-September

 Chestertown Marina 13 Sep 2025
FESTIVALS USD 23 TO 44