Chestertown Holiday Events

Holiday events Happening Next in Chestertown, MD

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

 25227 Chestertown Rd 21 Aug 2025
FOOD-DRINKS USD 75

Brampton 1860 Fall Open House

 25227 Chestertown Rd 7 Sep 2025
HOLIDAY FREE

Sultana's Downrigging-Festival Village Passes-2025

 Chestertown Marina 31 Oct 2025
FESTIVALS USD 28 TO 55

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

 Chestertown Marina 2 Nov 2025
USD 44 TO 71