Jim and Tracy have lived in Kent County for almost 30 years. They know the local restaurants extremely well and can make a recommendation for the best place to go based on your preferences. Below is a list of restaurants they often recommend to guests.
We’ve broken this list down by town to make it easier to find a restaurant in the area you’d like to explore:
Chestertown Historic District Restaurants
- 98 Cannon - Riverfront dining, lunch, brunch, and dinner
- The Kitchen at the Imperial - Historic Hotel, lunch, brunch, and dinner
- Evergrain - Bakery, coffee, breakfast, and lunch
- Stam's - Ice Cream, breakfast, and lunch
- Play it Again Sam's - Coffee shop, breakfast and lunch
- Figg's Ordinary - Gluten-free options, breakfast, and lunch
- Chester River Wine and Cheese
- Casa Carmen - Boutique winery and tapas
- Zelda's - Speakeasy
- Bad Alfred's - Distillery and brick oven pizza
- The Retriever - Bar, and dining for dinner
- Watershed Alley - Local authentic food from the Chesapeake
Rock Hall Restaurants
- The Harbor Shack - Waterfront dining, lunch, and dinner
- The Waterman's Crab House - Waterfront dining, lunch, and dinner
- The Wheelhouse - Waterview dining, lunch, and dinner
- The Inn at Osprey - Fine dining, dinner
- Baywolf - Austrian and regional cuisine, lunch and dinner
- Passages - Waterfront dining, lunch, and dinner
- Get the Scoop - Ice Cream
- Ford's Seafood - Seafood retail, breakfast, lunch, and dinner
- Java Rock - Coffee shop, sweets, and lunch
- Sweet Cheeks - Candy shop
- Anchor and Plow - Pizza and sandwiches, dinner
- Muskrat Alley Cafe - Gift shop, breakfast
- Chester River Seafood - Wholesale, retail, crabs, and more
Chestertown Restaurants Outside the Historic District
- Uncle Charlie's Bistro - Lunch and dinner
- Cafe Sado - In an old Mill, Sushi and Sashimi, lunch, and dinner
- Germaine's - Soups and Sandwiches, carryout
- Procolino's - Italian, pizza by the slice, lunch, and dinner
- Luisa's Cucina - Italian, pizza, lunch, and dinner
- Blue Bird - Local bar, pool tables, lunch, and dinner
- Ellen's Coffee Shop - Diner, breakfast, and lunch
- Beverly's Family Restaurant - diner, breakfast, and lunch
Restaurants in Georgetown, Kennedyville, Galena, Millington, and Betterton
- Fish Whistle at the Granary - Waterfront dining, lunch, brunch, and dinner
- Molly's - Sporting goods, home cooking, breakfast, lunch, and dinner
- The Kitty Knight House - Historic water view, brunch, lunch, and dinner
- Twinnies - Family style, breakfast, lunch, and dinner
- Two Trees - American, Vegetarian-friendly, lunch, and dinner
- Barbara's on the Bay - Waterview, American contemporary, lunch, and dinner