Restaurants in Chestertown

Best Restaurants in Chestertown

Watershed Alley 337 High St, Chestertown Seafood • $$

Customers` Favorites

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

4.5 Superb111 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

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

“The food was very good, especially the chicken mousse/pate and the roasted carrots/fennel appetizers. The service was mostly OK. But the server did not take away the cocktail glasses and the appetizer plates for far too long. In fact, when she served the mains, we had to move the plates out of the way. There were four of them.”

4.7 Superb163 Reviews

Customers` Favorites

Italian
Taco Pizza
Onion Rings
Cheese Pizza
York Style Pizza
Ziti Pizza
Greek Salad
Garlic Knots
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 Superb213 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 Superb61 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 Superb95 Reviews

Customers` Favorites

Pastries
Bakery
Baguette
Cinnamon Raisin
Sun Buns
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 Superb161 Reviews
Luisa's Cucina Italiana 849 Washington Ave, Chestertown Italian • $

Customers` Favorites

Mozzarella Caprese
Antipasto Italiano
Tiramisu
Garlic Bread
Veggie Pizza
Grilled Chicken
Calamari Fritti
Shrimp Riviera
Scallops Shrimp and Crab
Cheese Pizza

“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 Superb302 Reviews
Back 50 tavern 6520 Church Hill Rd, Chestertown Bar • $

“Great service, awesome people”

4.9 Superb36 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

“Best Bar in chestertown! great food and the best Bartenders!! absolutely love Fallon and Ally🥰”

4.4 Superb157 Reviews
The Shanty Beach Bar 21085 Tolchester Beach Rd, Chestertown Bar & Grill • $

Customers` Favorites

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

“Nice beach,nice bar and nice people”

4.4 Superb78 Reviews
The FREEZE 717 Washington Ave, Chestertown Fast Food • $

Customers` Favorites

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

“I’ve been coming to the freeze since I was a little kid, and it has never failed me as the most consistent ice cream place around. I’m glad they’ve been able to stay open so long, and after seeing a review criticizing the rise in prices, I’m thrilled seeing a traditional family owned ice cream parlor stay open in todays market. I’ll pay for their milkshakes any day. Without places like Procolino’s, Louisa’s, and The Freeze, the charm of Chestertown would dwindle for me and many others. I speak for all residents of Chestertown and people in the area that The Freeze is more than an ice cream place, it is a home. I love this place and always will.”

4.4 Superb132 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.”

4.3 Superb100 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
15

Subway

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

“I’m so glad Subway is back and it’s better than ever. Employees are kind, the food has been really good, everything is clean and their hours are good. It’s clearly well run. Try to hot honey chicken - yum!”

4.2 Good69 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!!!”

4.5 Superb81 Reviews

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

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

5 Superb6 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 Good160 Reviews

Customers` Favorites

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

“Took a ride to this distillery and I must say AL is a total badass!! Great sense of humor, good jokes, great wood fired pizza. Served his country and you can tell he has a passion for brewing some good beer and other spirits . Thanks for the great day and memories you made for us this day Al. Everyone should stop by to see him and take a bottle home with you!! See you and your staff again soon!!!”

4.2 Good130 Reviews
Milano's Pizzeria 6346 Church Hill Rd, Chestertown Pizza • $

Customers` Favorites

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

“The Rustics are divine!”

4.2 Good196 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 Good231 Reviews
McDonald's 875 Washington Ave, Chestertown Fast Food • $

Customers` Favorites

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

“The manager at this location was supper helpfully and polite I've got some health issues at the moment and she helped me get my order to my car and was so kind!”

3.7 Good148 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

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.”

3.8 Good174 Reviews
China House 711 Washington Ave #31, Chestertown Chinese • $

Customers` Favorites

Shrimp Fried Rice
General TSO’S Chicken
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.”

3.6 Good129 Reviews

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