Restaurants in Chestertown

Best Restaurants in Chestertown

Watershed Alley 337 High St, Chestertown Seafood • $$

Customers` Favorites

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

“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 Superb111 Reviews

Customers` Favorites

Vindaloo
Chicken Tikka
Chicken Biryani
Chana Masala
Rice with Butter Chicken

“Ordered takeout online. It was ready when I arrived. I got the Mutter Paneer, which was not bad, but honestly a little too sweet. I also got an order of Naan, which was great. Staff was friendly! Would eat here again!”

4.9 Superb58 Reviews
Phat Daddy's 205 Spring Ave, Chestertown Barbecue • $

Customers` Favorites

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

“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!”

4.7 Superb129 Reviews
Modern Stone Age Kitchen 236 Cannon St, Chestertown Health Food • $

Customers` Favorites

Pretzel
Croissant
Meat Pizza

“Thank you MSAK for serving delicious, nutrient dense foods with excellent customer service. We can’t get food this quality unless we make it ourselves at home so we travelled from TX to visit MSAK and it was worth every minute!”

4.6 Superb135 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 Superb63 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

“This is our go to place. You will never be disappointed in the food service or the vast knowledge of the mixology for a specific drink. Such a gem located so close to home. Just go, you will not be disappointed.”

4.6 Superb168 Reviews

Customers` Favorites

Italian
Garlic Knots
Ziti Pizza
Taco Pizza
York Style Pizza
Greek Salad
Onion Rings
Cheese 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 Superb223 Reviews

Customers` Favorites

Pastries
Baguette
Bakery
Sun Buns
Cinnamon Raisin
Chicken Balon Asparagus Pie
Apricot Ginger Scone
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 🏃‍♀️”

4.6 Superb171 Reviews

Customers` Favorites

Mexican Street Tacos

“We stoped by here on our way home from Rock Hall and were very impressed with the food and staff. The chicken mole pizza is something I have never seen before and was delicious.”

4.6 Superb58 Reviews
Luisa's Cucina Italiana 849 Washington Ave, Chestertown Italian • $

Customers` Favorites

Antipasto Italiano
Tiramisu
Mozzarella Caprese
Garlic Bread
Veggie Pizza
Grilled Chicken
Calamari Fritti
Scallops Shrimp and Crab
Chicken Wings
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!!”

4.5 Superb322 Reviews
Back 50 tavern 6520 Church Hill Rd, Chestertown Bar • $

“Great service, awesome people”

4.9 Superb36 Reviews
Antojitos Norma 840 High St, Chestertown Mexican • $

“This food truck has by far the best and most authentic Mexican food I’ve had in a very long time. My fiance and I frequent this place about once a week. We have tried a few items on the menu and nothing has disappointed yet. The prices are extremely reasonable for the platters they provide. I highly recommend trying them at least once while you’re in town.”

4.7 Superb12 Reviews
Milano's Pizzeria 6346 Church Hill Rd, Chestertown Pizza • $

Customers` Favorites

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

“The Rustics are divine!”

4.4 Superb232 Reviews
Blue Bird Tavern 512 Washington Ave, Chestertown Bar • $

Customers` Favorites

Seafood
Naked & Crispy Wings with Mango Habanero Sauce & Bleu Cheese
Ham \u0026 Cheese Club
Fried Oyster Basket
Chicken Cheesesteak
Chicken Caesar Sub
Chicken Salad Club
Rock Fish Sandwich
Shoe String Fries
Cheeseburger Club

“Annually, I come from Jacksonville, FL, to visit my sister, who lives a block away. It would be a sacrilege to not go to The Bluebird. Colloquial in the best sense of the word. It seems to have been modified , somewhat, in the last year but the charming, comfy, shredded barstools remain, thank god. The food is terrific. The sweet guy who cooks it comes out to serve and is conversational and earnest. Quite talented! We just love it. I hope you have a tshirt I can buy before I leave for home ❤️ 🌻 😊 I missed our regular barkeep but the lovely, young woman who served us was efficient and adorable. Couldn't ask for more in a neighborhood tavern 🌟⭐️🌟⭐️🌟”

4.4 Superb165 Reviews
The FREEZE 717 Washington Ave, Chestertown Fast Food • $

Customers` Favorites

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

“Heather was amazing Great customer service!!! We got the wing zings and fries chicken sandwich and ice cream cone twist which all were good very satisfied customer will be coming back!!”

4.4 Superb137 Reviews

More Restaurants in Chestertown

Customers` Favorites

Mint Chocolate Chip Milkshake

“Stopped in to sugar doodles at 8:45 to get some ice cream for my sons bday today. online it says they close at 10. Then noticed the door said 9. The place was packed! John handled it like a champ by himself! Def deserves a raise!”

4.5 Superb21 Reviews
Stam's Luncheonette 215 High St, Chestertown Ice Cream & Frozen Yogurt • $

Customers` Favorites

Tomato Soup
Chicken Salad Sandwich
Raspberry Ice Cream
Egg Salad Sandwich
Cookies and Cream
Breakfast Burrito
Mango Ice Cream
Ice Cream Pie
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!!!”

4.4 Superb84 Reviews

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

5 Superb6 Reviews

“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 Superb102 Reviews
Subway 834 High St, Chestertown Sandwich Shop • $

Customers` Favorites

Cookies
Raspberry Cheesecake Cookie
Chocolate Chip Cookie
The Hotshot Italiano
Oven Roasted Turkey
Lays Baked Original
Grilled Chicken
Subway Club

“This subway is great honestly, Sunny is a great guy and every time I come he is there and the food is great. Never been disappointed here. Thanks for the great service and good food!”

4.3 Superb70 Reviews
Channel Restaurant 21085 Tolchester Beach Rd, Chestertown Seafood • $$$

“This place is the best,I would eat here everyday the cook makes the best food and so kind,the waitress was so kind and her dessert are the best she’s so talented. I 100% recommend this place and everything is the perfect Quality!”

4 Good3 Reviews

Customers` Favorites

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

“First time trying Bad Alfred’s since buying a house here, and we are trying to get used to the limited selection of restaurants in this town after moving from Virginia. The food, drinks, and service was great. We will be back!”

4.3 Superb135 Reviews
Play It Again Sam 108 S Cross St B, Chestertown Coffee & Tea • $

Customers` Favorites

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

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

4.2 Good167 Reviews

“Resort bar vibes all the way! I love the chill atmosphere. The swings at the bar are so cool. We anchored out all weekend and could hear the bands and DJ from the boat. Loved it!”

4 Good88 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 Good248 Reviews
McDonald's 875 Washington Ave, Chestertown Fast Food • $

Customers` Favorites

Mcdouble
Quarter Pounder Hamburger
Sausage Mcmuffin with Egg
Chocolate Chip Cookie
World Famous Fries
Chicken Mcnuggets
Dasani Water
Cheeseburger
Apple Slices
French Fries

“The particulars of a McDonald’s review always hang on two factors. How well is the location run (how is the team and leadership) and is it clean?

Food is within 1% the same every time, which is why you come here right? The smile (or the scowl) of the team member that hands you the tray is a big part.

Today, things were all good with the team and food came fast. The Restaurant and the restroom were both in good shape and the dining room was in good order.

I can recommend this location. Thanks to this operator for my meal and the experience.”

3.7 Good154 Reviews
Dunkin' 715 Washington Ave, Chestertown Coffee Shops • $

Customers` Favorites

Donuts
Sandwich
Sausage Egg and Cheese
Everything Stuffed Bagel Minis
Munchkins Donut Hole Treats
Stuffed Biscuit Bites
Bacon Egg and Cheese
Dunkin' Refreshers
2 Egg & Cheese
Butter Pecan

“Ordered a couple breakfast sandwiches which were good. The order kiosk showed sesame bagels on the menu but location did not actually carry them so had to switch to get the order completed.”

3.7 Good70 Reviews

Customers` Favorites

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
Mango Brulee

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

3.8 Good179 Reviews
China House 711 Washington Ave #31, Chestertown Chinese • $

Customers` Favorites

General TSO’S Chicken
Shrimp Fried Rice
Orange Flavored Chicken
Shrimp w Lobster Sauce
Sweet & Sour Chicken
Chicken Noodle Soup
Shrimp Egg Roll
Pork Fried Rice
Sesame Chicken

“I love china house in Chesterton. Best take out food in town. Love the wontons and egg rolls, beef n broccoli, and the poo poo platter that has a little bet of every appetizer and the biggest fried chicken wings.”

3.7 Good142 Reviews

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