Fun spot found on the main street going through Chestertown that has solid eats. Can't miss their…read moresign. It's an independent burger joint/ice cream shop, and I love to support spots like these. Had a good burger with wonderful, crispy onion rings and a huge, tasty vanilla shake. All made in front of me. It's a throwback place with reliable cooking, quick service, and personable staff. Keep it up, Freeze. I'll be back.

Cute little mom and pop shop with something for everyone. Just some good, greasy food with homemade…read moretouches. So sweet and polite we got great service. Prices are very fair. Quick service. Ice cream and milk shakes are delicious. I wanted to try everything! Def a must when in chestertown!

The Retriever Oyster House in Chestertown left us with a mixed impression, one that deserves a fair…read moreand constructive take. We had just come from a college football game and, on the fly, decided to grab dinner here based on the recommendation of the one local in our group. There were seven of us, and most went for the double smash burgers with fries, which were excellent. Kim, our server, was outstanding, prompt, accurate, and attentive throughout the evening. The bartender also added to the positive side of the experience, making sure everything at the table ran smoothly. The issue came at the door. We had tried to call ahead to let them know we were on the way, not realizing that OpenTable was their preferred system. When we arrived, the host made this clear, but in a way that was unnecessarily sharp and cold. It set the wrong tone for the night. In a town where friendliness is the norm, the contrast was striking. The experience began under a haze that was difficult to shake, even though the food and drinks were excellent once we sat down. To be constructive, this is less about policy and more about hospitality. A host sets the tone, and a welcoming explanation could have changed everything. Something as simple as, "We usually use OpenTable to handle groups this size, but I'm glad you're here, let's get you taken care of," would have gone a long way. Instead of frustration, it could have created a positive first impression and likely earned a loyal group of returning guests for years to come. Inside, the atmosphere was lively, with locals enjoying themselves in a loud and fun environment. Our group of longtime friends who have been convening in Chestertown for two decades fit right in once we were seated. However, the bad first impression lingered, and as a result we only had one round with food before deciding to leave a lot earlier than our normal rhythm for an evening out. We ended up taking our bar bill to another venue. Great food and excellent table service carried the night, but the host made sure we will not be returning as part of our annual tradition. This is a restaurant with strong potential, and it could go from good to exceptional with just a little more attention to how guests are greeted.

Fantastic dinner experience at The Retriever Bar during our Chestertown getaway! We popped in while…read morestaying at Brampton 1860 and loved it. The House Burger was cooked exactly to perfection. We also tried the shrimp & grits, which arrived beautifully plated. We couldn't resist splitting the apple strudel for dessert, topped with locally made ice cream from Stams. Special shoutout to our server Kassie, who went above and beyond with her hospitality and gave us some great tips for things to do around Chestertown. The bar area has a great atmosphere too. We'll definitely be back on our next visit to Brampton to try more.

We stopped here while exploring the amazing Arts District. We were looking for some good beer and a…read morelate lunch after spending the morning at the farmer's market. The building is really cool, and there were already quite a few people dining in the main room. We prefer to sit at the bar, so we saddled up and were greeted by a friendly bartender. I'd give them a higher rating, but the beer selection was a bit limited. (It's technically a distillery, but they also brew beer.) The beer I had was decent, and my wife really enjoyed her seasonal cocktail. Now comes the really good part--the food. The menu was interesting, and there were several things we wanted to try. We settled on the pepperoni wood-fired pizza, and it was phenomenal. A lot of places get part of a pizza right but miss on others. Alfred didn't miss a thing: the crust was perfect, the sauce was spot-on, the toppings were generous, and there was so much cheese. We thoroughly enjoyed it. Another highlight was getting to meet Alfred and hearing the history of the company. It's obvious he has a passion for his business and customers, and it's clear he's well-liked in the community. We will definitely be back the next time we're in town.

One of the few places to eat in the area, so I was quite nervous about whether the food would be…read moregood or not. I was pleasantly surprised and can say the food was quite tasty. I had the High Street pizza and a Chestertown Moscow Mule...a pretty perfect dinner. There was the right amount of cheese on the pizza, and a good crispy crust. My son and his and both had cheeseburgers and tater tots and they both enjoyed their burgers. Service was good and everyone was very friendly.

Authentic Italian food!!! Large portions!!! Fabulous menu to choose from and everything comes out…read moreperfect and delicious!!! So hard to choose just one thing!!! Gluten free and wood fired pizzas as well. Friendliest staff!! Best to make a reservation, although lots of seating, fills up quickly as you can imagine!!!! Yum!!!!!!!

Sausage and mushroom pizza. Really, really good. Nice thin crust, delicious sausage and sauce and…read moretasty mushrooms. I've had many things from both the eat in and take out menus. Everything has been really good. Very nice place with a friendly staff.

Went here with my family a few times. Service is amazing, food is great and the interior is niceread more

Miles made our experience at The Kitchen! The food was delicious and fresh. I had the carnitas…read moretacos, and they had great flavor. Only 2 were served for $15 with no sides. That's a lot per taco! Add a side and it makes sense. The layout of the dining areas offers privacy for small groups. The decor and furniture could use some updates and repairs.

I just ordered for the first time and finished lunch. My mom had the 21-shrimp basket with fries,…read moreand I went for the Tex-Mex Chicken and Shrimp Quesadilla. We're in Chestertown, and we were hoping for warm food, and it did not disappoint, everythng came very hot! My mom really appreciated that the breaded shrimp didn't have tails. The meal was delicious, full of flavor, and arrived quickly. Overall, a fantastic experience, and I'd definitely recommend Go Mart to anyone!

Just called and ordered a ham and cheese sandwich on wheat bread with lettuce, tomatoe and mayo…read more I got a grilled cheese on white bread with one little piece of ham. I had to take apart the sandwich to find it. Not happy.

I came to Arby's wanting to try their food for the first time. I come in and this teenage girl…read morecomes in from the side door and asks if I need something. I tell her I want to order something and she laughs and says something like "okay then why don't you tell me what you want?" Really awkward. As I tell her my order, she looks like she's having a bad day which makes me feel more uncomfortable. My food comes out a few minutes later and the food was a 3/10. I got the cheese pit beef sandwich and fries. I couldn't taste the cheese on the sandwich and the fries were decent. Overall, i probably won't come here again. If you're an Arby's fan, be aware of this kind of service

Being a Sunday night, and nothing else in Chestertown open, i was surprised it was pretty clean,…read moreorder filled quick and the food well prepared. Portions seemed a bit small, the Pecan chicken sandwich had a small plop in the middle, not visible around the edges of the bread, not at all like the picture on the poster Sauce dispensers were out of the pepper sauce. My slider buns were soft however, so that was good ! Staff was super pleasant, and no pushback when I asked for extra Horsey Sauce packs. I noticed the drive through clock was averaging 240 seconds , which is not bad for an Arby's . I almost rang the "great service" bell, but figured they probably are tired of hearing it. I just thanked them the old fashioned way , verbally and sincerely .

Good food and drinks. Always good experience for lunch or dinner. The owners are great people as…read morewell.

Food is horrible. Beware if you get delivery. Trying to get issues fixed is a joke. This has…read morehappened twice. never again

Good cheesesteak. This is the best cheesesteak that I have found "in-town". Fast, friendly service…read more A good option when you want to stay local.

So Good, You Have to Pace Yourself!…read more Milano's is dangerously delicious--in the best way possible! The food is so consistently flavorful, fresh, and satisfying that we've had to put ourselves on a once-a-month limit just to keep from ordering every week. Seriously, it's that good. From the cheesy, melt-in-your-mouth pizzas to the perfectly seasoned pasta dishes and subs that hit every craving--you can taste the love in every bite. The portions are generous, the service is friendly, and everything always arrives hot and fresh. Milano's is our go-to guilty pleasure--but in moderation! You've been warned: once you try it, you'll want to come back again and again.

A very cute spot with beautiful decor and it almost feels like you're not even in Chestertown. The…read moreoutside of the building does not reflect the inside at all. Pros: The ambiance, french fries and lemongrass soup. I think because we got there an hour before closing, they were ready to go. The service was extremely slow and we were barely checked on by our waitress. My grandmother order a burger (well done), I had the pad Thai and Lemongrass seafood soup. The burger came out and was bleeding in the middle so we flagged down the host to have another made. My pad Thai was more on the sweeter side and really saucy. Different than I've had before but not too bad, it was better the next day for lunch lol. Id come back to try their sushi, I just wasn't fond of the service provided to us.

Our first time here. The location was nice. It's tucked away inside of small business building…read more Atmosphere was very cool. The waitress was good. The food was very good and fresh. The curry shrimp and rice was to die for. The sushi was very tasty.