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 HouseChesapeake 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.

Germaine’s – Delicious food with a New Orleans twist, featuring great salads and sandwiches.  Take out only.