There are plenty of adorable small businesses to check out in Chestertown. Some of our favorites are Village House, Welcome Home, and Chester River Wine and Cheese Co. Additionally, the town is full of art galleries to explore. We also recommend grabbing an ice cream at Stam's luncheonette.

Check out the Chestertown Farmers Market which occurs every Saturday morning and takes place in the middle of town.

Take a ride on the historic Sultana. A great way to explore the Chester River is to take a 2-hour ride on this replica 1700s era ship.

One of the best places to grab a cup of coffee and a pastry is Evergrain bread Co. Grab one of their famous everknots and people watch at their outdoor seating.

There are plenty of great options to have a meal in Chestertown. One of the best is Watershed Alley. They have a constantly rotating menu of farm to table favorites.

We recommend checking out the Retriever either for a casual dinner or a cocktail. They are best known for their raw bar but everything on the menu is excellent.