Crazy Days of Summer

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 of special promotions and savings at participating downtown merchants.

The Chestertown Quest Scavenger Hunt: NEW this year! Participate in our town-wide scavenger hunt for a chance to win hard, cold Chestertown Cash!

Food Sales: Grab a bite to eat and support a wonderful cause with on-site food sales hosted by the Animal Care Shelter for Kent County.

Extended Shopping Hours: Don't rush your trip—local downtown shops will be staying open late through the weekend to accommodate shoppers.

Bring your family, explore our beautiful downtown, and discover the unique character of Chestertown. We can't wait to see you there!