Restaurants in Chestertown

Best Restaurants in Chestertown

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

Customers` Favorites

Cornbread
Crabcake
Beef Carpaccio
Crab Soup
Shrimp and Grits
12 Oz Roseda NY Strip 40 Served with Maitre D’ Butter Cress and Choice of 1 Side Dish
Custard
Cod Loin
Broccolini
Duck Breast

“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 Superb61 Reviews

Customers` Favorites

Chicken Tinga Tacos
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
Burger and Fries

“Our waitress was great. Very informative about the food and just great with her service. Unfortunately we did not like the hamburger-very small, no onions or tomatoes - the rest of the food was good and the oysters great”

4.7 Superb46 Reviews

Customers` Favorites

Italian
York Style Pizza
Taco Pizza
Onion Rings
Greek Salad
Garlic Knots
Cheese Pizza
Ziti Pizza
Chicken Pizza
Pepperoni Pizza and Grilled Chicken Caesar Salad

“I’ve been going to Procs for over 35 years, the best pizza I’ve ever had, gnocchi is incredible, the sauce is like non other!! 5 stars for sure!!!”

4.6 Superb72 Reviews
Phat Daddy's 205 Spring Ave, Chestertown Barbecue • $

Customers` Favorites

Pulled Chicken
Baked Beans
Potato Salad
French Fries
Fish Sandwich
Macaroni
Rib Tips
Chicken Wings
Beef Brisket
Hush Puppies Served in Miniature Fry Basket

“Absolutely delicious! And the BBQ cooking aromas? - oh, my! We found friendly people from the minute we hit the door. The hushpuppies were awesome -- crispy on the outside and moist inside. TRULY the best!”

4.6 Superb65 Reviews

“HIGHLY recommend the Lemon Mascarpone cake!!! To die for! My mom, sister and I had a slice for dessert in North Carolina back in the spring, and have been wanting it ever since, and Happy Chicken came through for my moms birthday cake! Absolutely delicious!”

5 Superb14 Reviews
Modern Stone Age Kitchen 236 Cannon St, Chestertown Health Food • $

Customers` Favorites

Pizza
Pretzel

“Such a wonderful business that is constantly growing and expanding with new ideas that are both fun and functional! Truly passionate about giving back to the community and the work that they do. Plus everything is delicious!”

4.5 Superb62 Reviews

Customers` Favorites

Pastries
Bakery
Apricot Ginger Scone
Cinnamon Raisin
Sun Buns
Chicken Balon Asparagus Pie
Savory Croissant
Apple Rhubarb Pie
Iced Latte

“Saw a long line at the Crofton farmers market Saturday and decided whatever is that good, I'm going to need to try it. Really, no lines anywhere else. I waited in line the whole time my friends were seeing the entire rest of the market. It was a bakery, so I wasn't disappointed in my choice. This morning I had a bagel. OMG, the BEST bagel I've ever had! Perfectly chewy and crisp on the outside and soft on the inside. And I'm going to say it, it was better than the bagels I had in NY. There. I said it. We also got some hybrid muffin/croissant thing that is absolutely glorious. Excited to try to cookies and focaccia bread we bought. Evergrain bread company knows what they're doing. I will definitely be back. Heading to go follow their page now 🏃‍♀️”

4.5 Superb55 Reviews
Casa Carmen Wines 312 Cannon St, Chestertown Tapas/Small Plates • $$

“What a great place. The wine was wonderful. The experience was perfect. Meeting one of the owners we were able to gain the history. An amazing story. I strongly recommend a visit here. It's worth it”

4.7 Superb16 Reviews
Back 50 tavern 6520 Church Hill Rd, Chestertown Bar • $

“Great service, awesome people”

4.9 Superb9 Reviews
Blue Bird Tavern 512 Washington Ave, Chestertown Bar • $

Customers` Favorites

Naked & Crispy Wings with Mango Habanero Sauce & Bleu Cheese
Chicken Cheesesteak
Chicken Caesar Sub
Rock Fish Sandwich
Chicken Salad Club
Shoe String Fries
Cheeseburger Club
Fried Oyster
Clam Strips
Grilled Ham

“Great bar! Cold beer and the best crab cakes!”

4.5 Superb37 Reviews
Luisa's Cucina Italiana 849 Washington Ave, Chestertown Italian • $

Customers` Favorites

Tiramisu
Quiche
Veggie Pizza
Crab Dip
Mozzarella Caprese
Baked Ziti
Garlic Bread
Cheese Steak
Shrimp Riviera
Lasagna

“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 Superb90 Reviews
The FREEZE 717 Washington Ave, Chestertown Fast Food • $

Customers` Favorites

Sundaes
Chicken Sandwich
Ice Cream Cone
French Fries
Onion Rings
Strawberry Milk Shake
Cheeseburger
Cheese Steak
Hamburger
Steak Sub

“WOW very cool old school icecream and burger spot. We only had icecream. The small was huge!
I saw the man loading the soft serve machine with gallons of whole milk. REAL unadulterated icecream. Wife had a hot fudge Sunday and I had peanut butter topping because another patron before me had it and it looked scrumptious.
Just passing through but if I lived here it would be a weekly stop.”

4.4 Superb36 Reviews
The Shanty Beach Bar 21085 Tolchester Beach Rd, Chestertown Bar & Grill • $$

Customers` Favorites

Soft Pretzel
Blackened Fish Sandwich
Fried Rockfish Bites
Crab Cake Sandwich
Oven Roasted Wings
Chicken Tenders
Cheeseburger
Rum Bucket

“Nice beach,nice bar and nice people”

4.4 Superb32 Reviews
C-Town Liquors & Deli 601 Washington Ave, Chestertown Deli • $$

“To all my friends, I stopped at this deli and I got 2 Italian subs and they were the best I’ve ever had, The service was very friendly. If you’re ever in Chester town please stop by and visit them! They have the best subs in town.”

4.4 Superb20 Reviews
BAD Alfred's Distilling 323 High St, Chestertown Pizza • $

Customers` Favorites

Pizza
Crab Dip
Smoked Chicken Salad on Greens
Flank Steak Salad
Poblano Popper
Smoked Wings
Water Street
Side Salad

“I love this place! Alfred is wonderful and always makes sure he says hi to our table. The servers are pleasant and positive, the atmosphere makes me glad to be there. The art on the walls are beautiful and the FOOD 😍😍😍 Our family loves coming here.”

4.3 Superb67 Reviews

More Restaurants in Chestertown

Stam's Luncheonette 215 High St, Chestertown Ice Cream & Frozen Yogurt • $

Customers` Favorites

Chicken Salad Sandwich
Raspberry Ice Cream
Egg Salad Sandwich
Cookies and Cream
Breakfast Burrito
Mango Ice Cream
Ice Cream Pie
Tomato Soup
Turkey Melt
Patty Melt

“Stopped by today (8/18/2022) for the first time. An employee suggested the Butter Burger. Absolutely fantastic. My friend had Tuna Melt and said it was awesome. Will definitely visit this establishment again. *****stars!!!”

4.6 Superb34 Reviews
Play It Again Sam 108 S Cross St B, Chestertown Coffee & Tea • $

Customers` Favorites

Chicken Salad
Greek
Bag of Rise Up Coffee
Chai Blizzard
Alaskan
Norwegian
Roast Beef
blt Avocado
Italian Sub
Coffee Float

“Come down to Play it Again Sam for a yummy breakfast and coffee and follow us on our new page!”

4.4 Superb46 Reviews

Customers` Favorites

Mint Chocolate Chip Milkshake

“Amazing ice cream flavors. The holy cow was exactly what I wanted!!”

4.4 Superb22 Reviews

“Jackie was amazing to work with and made a custom ice cream flavor for my daughter’s birthday. I highly recommend 🍦❤️”

4.5 Superb2 Reviews
Milano's Pizzeria 6346 Church Hill Rd, Chestertown Pizza • $

Customers` Favorites

Special
French Fries
Pepperoni Bacon Italian Sausage w Extra Cheese Mozzarella Cheese Stix
Half and Half Pepperoni Pizza
Large Cheese Pizza
Cheese Steak
Cheese Fries

“The Rustics are divine!”

4.2 Good53 Reviews
Subway 834 High St, Chestertown Sandwich Shop • $

Customers` Favorites

Cookies
Chocolate Chip Cookie
The Hotshot Italiano
Oven Roasted Turkey
Lays Baked Original
Grilled Chicken

“The town is fortunate to have a Subway restaurant- but the overall experience is a bit lacking (like 4 instead of 5 stars lacking).

The menu is expensive but I don’t like that you can’t get the best price unless you order with app. Really?

The tables were clean and the staff was friendly. Helpful and knowledgeable too.

The meal was tasty and seems fresh- but with everything pre portioned and pre-prepped for building sandwiches, how do we know.

I think the bread choices save the day for this restaurant. I’m liking the Ghost Pepper option. That was tasty.

Vegetarian options: Veggie is in the name

Parking: Park on either side of the building

Wheelchair accessibility: Curb cut and one level access”

4.1 Good14 Reviews

Customers` Favorites

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

“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 Good102 Reviews

“Great spot on the water. Ticked away like a great secret. Beach bars and phenomenal bar tenders! always some live entertainment and friendly faces! The dirty banana is to die for!”

3.8 Good17 Reviews
Cafe Sado 870 High St, Chestertown Sushi • $$

Customers` Favorites

Crab Dip
Fiesta Roll Dragon Roll Americano Roll Ring of Fire Roll
Americano Roll and Spicy Scallop Roll
Chili Garlic Fried Rice
Chicken and Broccoli
Chicken Fried Rice
Japanese Edamame
California Roll
Lobster Tempura
Chicken Ramen

“Delicious, fresh and excellent service! Excited to tell my friends about Cafe Sado and will definitely be returning.”

4 Good46 Reviews

“I'm in the Chestertown area for business from time to time and this place is great. Very good food, not fancy, reasonable prices and good service.”

3.6 Good43 Reviews

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