Things To Do
Downtown Chestertown
High Street and surrounding area,
Historic downtown Chestertown is filled with shops, galleries, and restaurants. Check out the map in the visitor's guide for a layout of the local businesses.
Chestertown Farmers Market
300 & 200 Block of High St, Chestertown, MD 21620
Saturday from 8AM-12PM
Kent County Family YMCA
200 Scheeler Road, Chestertown, MD 21620
For YMCA members, the Chestertown YMCA is super nice and newly built in 2022. There is a large pool, cardio equipment and weights, fitness classes, pickleball, and much more!
Evergrain Bread Company
201 High Street, Chestertown, MD 21620
The best bakery in Chestertown! Offering a variety of baked goods, bread, and coffee. Our personal favorite is the sun buns!
Play It Again Sam
14 Washington Square, Chestertown, MD 21620
Cute cafe with coffee and sandwiches. Perfect for lunch!
For all the days along the way