Wine, dine and stay with the perfect date night or getaway at our Maryland bed and breakfast.

The Kitchen at the Imperial Hotel – Chestertown 410-778-5000
Closed Tuesdays. Very good food. It’s the place we partner with to do the wine pairing dinners for our guests.

Blue Heron Cafe – Chestertown 410-778-0188
Closed Sundays. Classic fine dining. A guest favorite.

Luisa’s – Chestertown 410-778-5360
Italian restaurant and pizzeria. Open every day. Pretty darn good!

Lemon Leaf Cafe and JR’s Pub – Chestertown 443-282-0004
Café open daily for breakfast, lunch and dinner. Pub open daily from 4 to midnight, serving food until 9pm.

Evergrain Bread Company – Chestertown 410-778-3333
Fantastic European style bakery; espresso, cappuccino, light lunches. We have two places to catch up on local gossip. This is one of them.

The Fish Whistle – Chestertown 410-778-3566
Open every day. Decent food. This is the only restaurant in Chestertown with great waterfront view.

Play It Again Sam’s – Chestertown 410-778-2688
Open most days. Coffee house, light lunch. The other town gossip central.

Uncle Charlie’s Bistro – Chestertown 410-778-3663
Open every day for lunch and dinner. A nice menu with a little bit of everything. OK food.

Barbara’s on the Bay – Betterton 410-348-3079
Classic comfort food and spirits. Terrific deck with water view of the Sassafras River.

Molly Mason’s – Kennedyville 410-348-2430
Restaurant open every day of the week. Great for burgers etc.

Osprey Point Restaurant – Rock Hall 410-639-2762
Closed Monday and Tuesday and the month of January. Fine dining in Rock Hall. A bit pricey.

Waterman’s Crabhouse Sharp Street Wharf – Rock Hall 410-639-2261
Closed during the winter months. Casual waterfront seafood restaurant. The only restaurant in our area offering steamed crabs during the summer. Live music on weekends. Pricey and so-so for a crab house.


Molly's restaurant in Maryland



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Luisa’s