Restaurants in Chestertown

Best Restaurants in Chestertown

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

Customers` Favorites

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

“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!”

4.7 Superb66 Reviews

Customers` Favorites

Burger and Fries
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

“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”

4.8 Superb51 Reviews

Customers` Favorites

Garlic Knots
Italian
York Style Pizza
Ziti Pizza
Taco Pizza
Onion Rings
Greek Salad
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!!!”

4.7 Superb67 Reviews
Phat Daddy's 205 Spring Ave, Chestertown Barbecue • $

Customers` Favorites

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

“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 Superb71 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 Superb13 Reviews
Luisa's Cucina Italiana 849 Washington Ave, Chestertown Italian • $$

Customers` Favorites

Quiche
Tiramisu
Chicken Wings
Mozzarella Caprese
Crab Dip
Baked Ziti
Garlic Bread
Cheese Steak
Chicken Marsala
Shrimp Riviera

“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 Superb81 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 Superb19 Reviews

Customers` Favorites

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

“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 Superb52 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
Modern Stone Age Kitchen 236 Cannon St, Chestertown Health Food • $

Customers` Favorites

Pizza

“Just exemplary! This is food that we are meant to eat. Nose to tail. Fermented. Nixtamalization corn, no seed oils, no refined sugar, local grass fed beef, low pasteurized dairy, hydroponic greens, etc. And everything fermented- sour dough bread, rolls, pasta, pretzels, cookies, pastries, doughnuts, breadcrumbs, waffles, pancakes, and so much more. All local meats, honey, homemade condiments, yogurt, cream cheese, scrapple, bacon, beef, etc.! Bill and Christina Schindler and their children and team are invaluable. Buy Eat Like A Human book by Bill, and visit this incredible place to experience the most beautiful dining and shopping experience ever!”

4.4 Superb51 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

“This is a small little ice cream place but the food was so good. The crispy chicken sandwich and the burger were great and their prices are reaaonable. Not a lot of room to ait and eat in but nothing wrong with to go either.”

4.4 Superb46 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
15

Subway

Subway 834 High St, Chestertown Sandwich Shop • $

Customers` Favorites

Lays Baked Original
Grilled Chicken

“I forgot subway had opened back up and my girlfriend mentioned it so we went today to get a sub for each of us she got the chicken bacon ranch which is phenomenal and I of course got my old Philly and man it taste like the subway ya want the service was great and the subs are awesome thank you to the owner for revamping and giving it a shot it’s about time we got subway back! Will be back for more!”

4.4 Superb9 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 Superb37 Reviews
Play It Again Sam 108 S Cross St B, Chestertown Coffee & Tea • $

Customers` Favorites

Greek
Roast Beef
Chicken Salad
Bag of Rise Up Coffee
Chai Blizzard
Alaskan
Norwegian
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 Superb40 Reviews

Customers` Favorites

Mint Chocolate Chip Milkshake

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

4.4 Superb22 Reviews

Customers` Favorites

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

“We brought in three kids ten and under in, tired from a road trip. They were clearly teetering on being unfit for public consumption. We ordered a great crab dip appetizer before realizing the kids weren't going to make it before the pizza arrived. The staff at Bad Alfred's was so terrific at accomodating us after we asked for all of our meals to immediately get boxed up to go, even bringing out the check with the boxes. Many places would not act so expeditiously and with such kindness. We even got called "such a great family," which was probably undeserved. Seriously, these folks were saints - we can't say enough positive things about them. The food, which we ate much later, was delicious.”

4.3 Superb65 Reviews

Customers` Favorites

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

“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 Good100 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!”

3.7 Good12 Reviews
Milano's Pizzeria 6346 Church Hill Rd, Chestertown Pizza • $

Customers` Favorites

French Fries
Special
Half and Half Pepperoni Pizza
Large Cheese Pizza
Cheese Steak
Cheese Fries
Italian

“The Rustics are divine!”

3.9 Good53 Reviews
Dunkin' 715 Washington Ave, Chestertown Coffee Shops • $

Customers` Favorites

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

“Chestertown Dunkin is the best I never have to wait for my orders. Everyone is always so nice and gives amazing customer service. Dwinda and Vince are amazing. I’m there every morning on my way or days and the morning staff in general is awesome. I’ll start learning more peoples names.”

3.6 Good32 Reviews
McDonald's 875 Washington Ave, Chestertown Fast Food • $

Customers` Favorites

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

“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!”

3.6 Good34 Reviews
Arby's 707 Washington Ave, Chestertown Fast Food • $

Customers` Favorites

Buffalo Chicken Sandwich
Chicken Slider
Smokehouse Brisket
Apple Turnover
Salted Caramel & Chocolate Cookie
Loaded Italian
Side Salad
Potato Cakes
Buffalo Slider
Loaded Curly Fries

“A positive experience from most of the staff. One of which is myself. And good food that will keep you coming back for more.”

3.6 Good39 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.”

3.7 Good59 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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