Restaurants in Chestertown

“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!”

“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”

“This was our fourth dinner at The Retriever and we had another wonderful evening. The food is consistently very good, service is efficient and friendly and you can't beat the cocktails. Plus it's reasonably priced. We share incredibly fresh oysters and the smoked bluefish dip for starters. Among the four of us we had the shrimp burger, the pork and noodles and the catfish. Everyone enjoyed their entrees. We will definitely be back to this charming spot.”

“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!!!”

“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!”

“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!”

“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!”

“Great service, awesome people”

“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 🏃‍♀️”

“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!!”

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

“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.”

“Nice beach,nice bar and nice people”

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

“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.”

“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!!!”

“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!”

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

“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!”

“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!”

“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.”

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

“The Rustics are divine!”

“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.”

“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!”

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

“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.”