7 Best 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
Crab Cakes with White Asparagus
Artisanal Cheese Board 1 Man
Chocolate Praline Torte
Watershed Angus Burger
Potato and Clam Chowder
Green Cherry Tomatoes
Red Acres Bibb Salad
Walnut Dacquoise
Shrimp and Grits

“My wife and I stopped in on a whim on the way home from catching up with family in Centreville. I'm vegan which has its challenges when it comes to navigating menus but Watershed made a vegan plate on the fly which was absolutely amazing. Serving staff was absolutely stellar as well! Wholeheartedly recommended, we will most certainly be back!“

4.5 Superb54 Reviews
Channel Restaurant Seafood • $$$
21085 Tolchester Beach Rd, Chestertown
5 Superb1 Reviews
The Retriever Bar & The Decoy Bottle Shop Bar • $$
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

“While riding the motorcycle, I happened into this gem of a restaurant. The atmosphere is very chill and the staff super friendly.

I ordered an Old Fashioned (with mezcal), while my friend had an EVO pale ale.

For dinner, I had a House Burger and my friend had a Cubanato. Both were delicious, as evident by the clean plate. (I apologize for forgetting to photograph the meals, but trust me, they were amazing...right down to the fries!)

I will most definitely return. This place is, in a word, awesome.“

4.5 Superb70 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
Chicken Fiorentina
Chicken Parmigiana
Antipasto Italiano
Margherita Pizza
Chicken Marsala

“Was extremely yummy. Had the veggie pizza and was delicious, also the cream of crab soup was so delicious!! Beautiful restaurant. Heather our server was awesome!!“

4.4 Superb79 Reviews
The Kitchen at the Imperial American • $$
208 High St, Chestertown

Customers` Favorites

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

“Wonderful atmosphere. Great food. Great staff as well. We had an amazing time. The best experience from the pre dinner drinks to the last bite of dessert.“

4.2 Good82 Reviews
Buddys Crabs Seafood • $$
2756 Church Hill Rd, Centreville - 8.17 miles

“Great crabs! Great people!“

5 Superb4 Reviews
Kitty Knight Inn Seafood • $$
14028 Augustine Herman Hwy, Galena - 10.19 miles

“I grew up in the area and have eaten here many times. This is the best the food has ever been! The new chef is incredible and the atmosphere is perfect. Great deck and beautiful views outside! This is definitely our new favorite spot again!“

3.8 Good20 Reviews

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