Get ready to support local, shop small, and have a blast! Crazy Days in Chestertown is back for a massive three-day local shopping event in our historic downtown district. Whether you are looking for great deals, fun activities, or delicious food, there is something for everyone to enjoy all weekend long: Discounts Everywhere!!! Take advantage […]
Step back in time and experience the magic of the holiday season at A Dickens of a Christmas! Our charming downtown will be transformed into a Victorian winter wonderland filled with carolers, holiday markets, carriage rides, and festive cheer. Stroll the streets, sip hot cider, and enjoy a celebration straight out of a classic storybook. […]
Shop Smart, Shop Small. Show your love for your local, independent businesses and do your holiday shopping in Downtown Chestertown.
Downtown Chestertown businesses have had extended hours, refreshments, and special discounts for your holiday shopping needs.