For guests seeking incredible cuisine near our Eastern Shore B&B, these Chestertown, MD restaurants come with our highest personal recommendation. All these premier dining destinations are in the area surrounding the Inn and offer a delicious variety of food with a distinctly Maryland flair.
Barbara’s on the Bay – Some of the best food in the area! While specializing in comfort food, they use local vendors, fresh seafood, and top-notch service. In Season they are open Wednesday through Sunday. In the Winter they are open Thursday through Sunday.
The Kitchen at The Imperial – This is the place to go if you are looking for the best crab cakes! A Chef owned restaurant with a seasonal local menu.
Uncle Charlie’s Bistro – A favorite place of the locals. Enjoy a wide and varied menu!
Luisa’s – Best Italian food you’ll ever eat! Ranked #9 out of 12 in the state of Maryland.
Fish Whistle – Featuring all things seafood and right on the water of the Chester River.
Osprey Point Restaurant – Located in Rock Hall and fantastic for special occasions.
Waterman’s Crab House – Chesapeake Bay waterfront dining located in Rock Hall.
Harbor Shack – A great place for local seafood on the waterfront with a casual environment in Rock Hall.
Evergrain Bread Company – Wonderful selection of breads and sandwiches.
Chester River Wine & Cheese Co – Lunch menu featuring cheese & charcuterie boards, as well as salads and sandwiches.
Play It Again Sam – Featuring coffee, hot teas, sandwiches, etc.