Seafood Restaurants near Chestertown

Watershed Alley Seafood • $$$
337 High St, Chestertown

Customers` Favorites

12 Oz Roseda NY Strip 40 Served with Maitre D’ Butter Cress and Choice of 1 Side Dish
Chocolate Praline Torte
Watershed Angus Burger
Red Acres Bibb Salad
Shrimp and Grits
Brussels Sprouts
Broccolini
Duck Breast
Cornbread
Crab Cake

“What an amazing dining experience! We recently celebrated our anniversary in Chestertown and the Watershed Alley was highly recommended. We certainly weren't disappointed! Our server was so nice and she made sure our experience was perfect.We had beef carpaccio and octopus for appetizers. The octopus was some of the best I've ever had- so tender! For dinner my wife had a strip steak and I tried the venison. They were both cooked to perfection and I don't think I've ever had venison that was as tender and tasty as this. We shared the brussel sprouts, and after trying them, I probably would have placed six more orders because they were so good.It was very busy, but it wasn't so loud that you couldn't hold a conversation. With that said, I would recommend making a reservation.Looking forward to making the trip back to Chestertown just so we can eat at the Watershed! Keep up the great work!“

4.7 Superb61 Reviews
The Retriever Bar & The Decoy Bottle Shop Bar • $$
337 1/2 High St #339, Chestertown

Customers` Favorites

Locally Sourced Oysters on the Half Shell
Bluefin Dip Fresh Dill and Pickled Onion
Orchard Points - Kent County MD
Huge Beer and Wine Selection
Bluepoints - Connecticut
Chicken Tinga Tacos
Burger and Fries

“I recently discovered The Retriever Bar & The Decoy Bottle Shop. The owner, Neyah, is down-to-earth and knows his stuff when it comes to high quality spirits. I was impressed by their extensive collection of highly sought after bottles such as Fortaleza (blanco, reposado, and añejo), not to mention the allocated bourbons they had available for tasting with options for both full and half pours. The food was the cherry on top! I also got to walk about with a bottle of G4 Repo and XA! Will definitely be returning here. Salud!!Dietary restrictions: I am gluten sensitive and they were super accommodating!“

4.9 Superb47 Reviews
Luisa's Cucina Italiana Italian • $$
849 Washington Ave, Chestertown

Customers` Favorites

Scallops Shrimp and Crab
Tomato Basil Salad Fresh
Gnocchi in Vodka Sauce
Luisa Supreme Pizza
Mozzarella Caprese
Antipasto Italiano
Margherita Pizza
Veal Parmigiana
Calamari Fritti
Chicken Marsala

“We dined here on a Thursday early evening.The servers were friendly and there was a nice atmosphere.There was a longer than expected wait for the food and upon finally being served, the food was not hot. The portions are average, it's unlikely you'll be bringing any food home.OVERALL: I recommend this restaurant.“

4.5 Superb88 Reviews
Channel Restaurant Seafood • $$$
21085 Tolchester Beach Rd, Chestertown
3 Average1 Reviews
The Kitchen at the Imperial American • $$
208 High St, Chestertown

Customers` Favorites

Whiskey N Dessert Chcolate Bread Pudding Red Velvet
Crispy Brussels Sprouts
Smashed Potatoes
Chicken Alfredo
Flank Steak
Lamb Chops
Crab Dip
Fries

“We went for an anniversary dinner and the place was fabulous. Great service and a great table in the front window area. Mostly local people eating there and they all said that this was the best restaurant in Chestertown. Definitely recommend it.“

4 Good84 Reviews
Buddys Crabs Seafood • $$
2756 Church Hill Rd, Centreville

“I must say it’s been about 3 years ago I stumbled upon this place . And it’s to a point when crab season is over I’m done I’m one who loves crabs all year round but it’s just not worth it anywhere else . Buddy’s has certainly get 4.75 stars only because I would like to be able to get more unfortunately the ones I like are not always available. Thanks for customer great service.Vince ( Glen Burnie)“

5 Superb5 Reviews
Kitty Knight Inn Seafood • $$
14028 Augustine Herman Hwy, Galena

“Group of nine met at Deep Blue @ Kitty Knight for a meal together on a quiet winter day. Most of us had dined here years ago before Deep Blue was operating. Interior of restaurant is lovely and much improved. Our group enjoyed lobster rolls, salmon/sides, crab mac&cheese, pork chop/sides and soup. Everyone loved their meals. Service spot on. Looking forward to trying brunch one Sunday (10-1).“

3.8 Good46 Reviews
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