8 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!“

4.6 Superb123 Reviews
Channel Restaurant Seafood • $$$
21085 Tolchester Beach Rd, Chestertown
4.3 Superb4 Reviews
Luisa's Cucina Italiana Italian • $$
849 Washington Ave, Chestertown

Customers` Favorites

Scallops Shrimp and Crab
Tomato Basil Salad Fresh
Gnocchi in Vodka Sauce
Veal Parmesan Pasta
Luisa Supreme Pizza
Chicken Parmigiana
Antipasto Italiano
Chicken Fiorentina
Mozzarella Caprese
Chicken Parmesan

“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!!“

4.6 Superb344 Reviews
The Retriever Bar Bar • $$
337 1/2 High Street Suite 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
Chicken Wings

“Our party of 4 came for dinner on a Friday evening and with our reservation, we were sat immediately. Our server was Tessa, who was delightful, and provided top notch service. We enjoyed oysters from ME and WA, along with Bluefish Dip, Arancini, and Buffalo Fries. Entrees were mostly burgers, and a salad. Food and drinks were all delicious, and everything came out in a timely fashion. We ended with a Blueberry Handpie to go - also quite good! This is an adults only bar in a beautiful setting, and extensive drink menu, including wine and cocktails. Would definitely recommend!“

4.6 Superb179 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.“

4.1 Good266 Reviews
Chester River Seafood Seafood Markets • $$
4954 Ashley Road, Rock Hall - 10.01 miles

“Once again, Chester River seafood trumps all crabs in the area! Picked up a half bushel this morning, every crab is hard and heavy! And the lump crab meat is beautiful! Thank you so much, well worth the long drive to get the best! 🦀 I will definitely be back!“

4.9 Superb61 Reviews
Buddys Crabs Seafood
2756 Church Hill Rd, Centreville - 8.17 miles

“Great crabs! Great people!“

4.8 Superb14 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!“

3.9 Good69 Reviews

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