Restaurants in Chestertown

1 Watershed Alley

4.6 Superb 132 Reviews

337 High Street, Chestertown

• Delivery
• Drive-Through

“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!”

2 Happy Chicken - Bakery & Catering

4.8 Superb 101 Reviews

215 Scheeler Road, Chestertown

• Take-Out
• Delivery

“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!”

3 Luisa's Cucina Italiana

4.6 Superb 348 Reviews

849 Washington Avenue, Chestertown

• Take-Out
• Drive-Through

“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 Phat Daddy's

4.7 Superb 152 Reviews

205 Spring Avenue, Chestertown

• Take-Out
• Drive-Through

“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!”

5 Evergrain Bread Company

4.6 Superb 185 Reviews

201 High Street, Chestertown

• Take-Out
• Drive-Through

“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 🏃‍♀️”

6 The Retriever Bar

4.6 Superb 183 Reviews

337 1/2 High Street Suite 339, Chestertown

• Take-Out
• Drive-Through

“We love the Retriever! Everything about it is amazing- the food, the bar program, and the service. All of that, and the space is beautiful, and the staff is friendly and knowledgeable about both the food and beverages.”

7 Modern Stone Age | Kitchen, Food Lab & Sanctuary (B&B)

4.6 Superb 159 Reviews

236 Cannon St, Chestertown

• Take-Out
• Drive-Through

“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!”

8 Howard's Tavern

4.9 Superb 37 Reviews

6520 Church Hill Road, Chestertown

• Delivery
• Drive-Through

“Great service, awesome people”

9 El Rancho Mexican Cuisine

4.6 Superb 77 Reviews

851 Washington Avenue, Chestertown

• Take-Out
• Delivery

“Very friendly service, excellent margaritas, and tasty food. We had the El Rancho Parrillada for 2, and it was amazing. We also had their rib special for dinner, and the ribs were super tender. Highly recommended - we will be back!”

10 Procolino's Pizza

4.5 Superb 243 Reviews

711 Washington Avenue Suite 9, Chestertown

• Take-Out
• Drive-Through

“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!!!”

11 Blue Bird Tavern

4.5 Superb 173 Reviews

512 Washington Avenue, Chestertown

• Drive-Through

“Great food with lots of options for reasonable prices. what more can you ask for ?”

12 Riley's Mill Ale Works

5.0 Superb 14 Reviews

860 High Street, Chestertown

“We stopped in to check out Riley’s Mill and Ale Works on a Sunday, it is a low key, friendly environment. We had a couple of their original beers and they were outstanding!”

13 Antojitos Norma

4.8 Superb 18 Reviews

840 High Street, Chestertown

• Delivery

“The food here is top of the line. If you like authentic Hispanic cuisine this is the place. Everything here is made fresh daily and you can tell. My favorite spot in Chestertown thus far.”

14 BAD Alfred's Distilling

4.4 Superb 154 Reviews

323 High Street, Chestertown

• Take-Out
• Drive-Through

“My husband and I visited last weekend for the first time and I certainly hope to be back. The pig and fig pizza was delicious. Can’t remember which wine I ordered, but the pour was great. My husband said the wings were excellent. We were served quickly and efficiently. Great little location in Chestertown.”

15 C-Town Liquors & Deli

4.4 Superb 109 Reviews

601 Washington Avenue, Chestertown

• Take-Out
• Drive-Through

“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.”

Stam's Luncheonette

4.5 Superb 95 Reviews

215 High Street, Chestertown

• Delivery
• Drive-Through

“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!!!”

Sugar Doodles Sweet Shop

4.6 Superb 33 Reviews

315 High Street, Chestertown

• Delivery

“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!”

Lockbriar & Daughter ice cream

4.9 Superb 8 Reviews

10051 Worton Road, Chestertown

• Take-Out
• Drive-Through

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

Channel Restaurant

3.8 Good 5 Reviews

21085 Tolchester Beach Road, Chestertown

• Take-Out
• Drive-Through

“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!”

The Shanty Beach Bar

4.3 Superb 88 Reviews

21085 Tolchester Beach Road, Chestertown

• Drive-Through

“Nice beach,nice bar and nice people”

The FREEZE

4.3 Superb 157 Reviews

717 Washington Avenue, Chestertown

• Take-Out
• Drive-Through

“Poor management of inexperienced wait staff. To top it off, let's serve raw cheeseburger . It went straight in the garbage can. This place was on point at one time. Not so much any more”

Play It Again Sam

4.2 Good 178 Reviews

14 Washington Square, Chestertown

• Take-Out
• Drive-Through

“World class Sausage Biscuits!”

Subway

4.1 Good 78 Reviews

834 High Street, Chestertown

• Take-Out
• Drive-Through

“This is hands down the best Subway in the state, possibly the country. The restaurant and restrooms are always clean and well lit. The food is always consistent with Subway's promises, but where this location really shines is the staff and management. Even if it's your first time there, you're treated more like a neighbor than a customer.”

The Kitchen at the Imperial

4.2 Good 268 Reviews

208 High Street, Chestertown

• Take-Out
• Drive-Through

“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.”

Milano's Pizzeria and Grill

4.2 Good 269 Reviews

6346 Church Hill Road, Chestertown

• Take-Out
• Drive-Through

“The Rustics are divine!”

Starbucks Coffee Company

3.9 Good 62 Reviews

504 Washington Avenue, Chestertown

• Take-Out
• Delivery

“I took 1 star off only because the little lady with the over sized glasses seemed to make me feel bad for placing an order on the mobile app and then getting there too early. She said it wasn't busy then, but next time there may be more customers so I shouldnt get there before the time ot says my order was ready. I was 2 minutes early. That being said, the coffee is always exceptional. Thank you!”

Dunkin'

3.8 Good 77 Reviews

715 Washington Avenue, Chestertown

• Take-Out
• Delivery

“Long drive thru line in the morning. When you go inside an order the cashier takes your order then run back to put it in drive thru cash register. They only thing is I had order a ice coffee. They had put honey in it when I didn't order any sweetener. Never paid attention to the ingredients on the side until I was at work. Could not return because I work a 12 hour shift with people that I take care of. Please double check a person order before giving it to them.”

Cafe Sado Chestertown

4.0 Good 200 Reviews

870 High Street, Chestertown

• Take-Out
• Drive-Through

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

China House

3.9 Good 147 Reviews

711 Washington Avenue Suite 31, Chestertown

• Take-Out
• Drive-Through

“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.”

Arby's

3.6 Good 154 Reviews

707 Washington Avenue, Chestertown

• Take-Out
• Drive-Through

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