Location: Chestertown
Top Restaurants in Chestertown
Where to Eat in Chestertown: The Best Restaurants and Bars
With a colonial history dating back to the 17th century, Chestertown, Maryland is proud of its maritime heritage. Sitting on the banks of the Chester River, sailing ships can still be seen coming into port. The city is the home of the Schooner Sultana, an exact replica of an 18th century ship that served in the British Royal Navy, now operating as an educational vessel. Every Memorial Day, the city hosts The Chestertown Tea Party Festival, proudly tossing the British overboard annually.
Things to do in Chestertown
1. Luisa's Cucina Italiana
Overall Ratings
4.5 based on 212 reviews
Welcome to Luisa's Cucina Italiana. Our dishes are prepared with locally grown fresh ingredients from St. Brigid's, Cedar Run, Lovett, and Redman Farms. Seafood, vegetables, poultry or meats... You'll find them to be superb! We offer catering for special occasions and private parties, as well as a semi-private dining area for family gatherings, business lunches, or dinners. Gift certificates available. Reservations recommended.
Reviewed By MycroftHolmey - Bastia, France
The food is great and always fresh and the ambiance is warm and welcoming. It’s s great place for dinner with friends or family. I highly recommend the chicken Parmesan, but everything’s good.
2. Evergrain Bread Company
Overall Ratings
4.5 based on 161 reviews
Reviewed By hildegaard - Baltimore, MD
Fresh baked breads, pastries and other treats in an open, airy space. The bakery is a coffee shop, a bread shop and a social hub for professionals, students, families, tourists and interesting locals. Friendly employees offer great service and small town charm. Local and organic dairy products and sandwichs available to take home.
3. Dunkin' Donuts
Overall Ratings
3.5 based on 13 reviews
Reviewed By Carolyn S - Lambertville, New Jersey
The good news? The donuts are good. The bad news? The Royal Farm Store out on highway 213 has Krispy Kreme. More bad news? This outlet seems understaffed and just doesn't fit in with the town. It's the only chain store downtown and ... it's just not good.
4. Uncle Charlie's Bistro
Overall Ratings
4.5 based on 164 reviews
Reviewed By Susan H - Georgetown, Maryland
My daughter and I stopped in for a quick bite since it was burger night. I got the cob salad with oysters and she had the burger. The salad was huge and great!! Most times you only get 1 hard boiled egg- here you get two.
The burger was cooked perfectly and was so tasty!! It's great that you are offered 3 different sides at no extra cost (usually extra for sweet potato fries or onion rings).
5. Figg's Ordinary
Overall Ratings
4 based on 10 reviews
Reviewed By Heady-By - Mechanicsville, Maryland
Stopped in on a whim. The sandwiches (mozzarella & tomato on one, veggies and Wisconsin cheddar on the other) were tasty - tastier without the bread, as the other ingredients were fresh, and with just an extra bit of S&P. We also bought two jelly doughnuts (OK) and two mocha chocolate chip cookies (wonderful!). All in all, we'd go back, but next time for salads, as the bread just wasn't for us. Give them a try!
6. Chester River Wine & Cheese Co
Overall Ratings
4.5 based on 41 reviews
Located in the vibrant Arts & Entertainment District of Chestertown, Maryland, Chester River Wine & Cheese Co. is a specialty food market offering international and domestic wine, cut-to-order cheese, charcuterie and pate, as well as gourmet foods such as handmade jam, mustard, salts and sweets, olive oils and vinegars. In addition to our retail offerings, we also provide onsite table service of select wine, cheese, and desserts in our informal gourmet shop atmosphere. Our menu changes the first Friday of every month. Every cheese board includes bread from our local bakery, chutney and mustard, dried fruit and nuts. We have tables inside and out and are fully wheelchair accessible. Families are welcome. Seating is limited; groups of 6 or more are encouraged to call us to ensure availability. Our table service begins at 11:30 and cheese board service ends one hour before closing. We empathize that many guests may want to sit and enjoy a glass of wine after our "kitchen closes" but we hold firm to our "kitchen closure time." As a family run business we do this to ensure a positive work/life balance for employees. Please note, we respectfully request that guests not consume retail purchases at our tables after "kitchen closure time" so that our team may focus on closing our retail counter and final shop closing procedures.
Reviewed By businesstraveler44 - Mid Atlantic
It's a cheese shop, but a very good one, especially when you consider that Chestertown isn't close to anything, so they have a limited market. Cheese selection is reasonably large, and they will let you taste before you drop down your cash. While not really the place for wine, they normally have a bottle or two open for you to taste, and occasionally you will run into a surprise that won't break the bank and is worth buying a bottle or two. They excel at customer service, which is why you go back. They talk to customers, listen to what you are interested in, and give you valid ideas.
Even if you don't particularly like cheese or wine, the experience in the shop is certainly worth the stop
7. The Fish Whistle
Overall Ratings
3.5 based on 414 reviews
Reviewed By mekopp - [email protected]
I visit here from time to time, but have never reviewed the restaurant before. I usually stop in and sit at the bar. I love the view of the Chester River from the restaurant and bar. Everyone is very friendly and its a nice atmosphere. I usually order the beet salad, which is the most amazing beet salad I have ever had. The first time I ordered it, it was simply because I wasn't that hungry but wanted to snack on something. This is NOT a snack. It is an absolutely huge beet salad with lots of glazed walnuts, goat cheese, and, of course, beets! The last time I visited my husband and I split a sandwich and the beet salad. So good. Parking is easy here and I always enjoy walking around historic Chestertown. It's one of my favorite places to visit.
8. The Kitchen at the Imperial
Overall Ratings
4 based on 149 reviews
Casual fine dinning in a relaxed environment. All food made from scracth. Offering lunch and dinner 5 days a week. Sunday offering a Bloody Mary Brunch with a build your own Bloody Mary Bar starting at 10am, dinner on Sunday starting at 5pm. Outdoor seating both front and back.
Reviewed By zimmerang - Joppa, Maryland
We had heard that the food was great, but ours was just good. However, the bartender didn't know how to make a basic drink. My Crown Royal and water came in a tall, slender iced tea glass and my wife's mojito was all liquor and no club soda (we had to ask for a separate glass of club soda to mix in the drink).
9. Procolino's Pizza
Overall Ratings
4.5 based on 65 reviews
Reviewed By PhreedomPhun - St. George, Utah
Really good sausage pizza, friendly owner and casual environment. This place is huge, so if you have a group it is the place to go. The take-out system they have is very organized and efficient too I noticed.
10. Cafe' Sado C-Town
Overall Ratings
4 based on 35 reviews
Reviewed By Michael Y - Keedysville, Maryland
We had dinner at Sado Café on 2/6/17. The location is very convenient, decent parking and the building is really nice. The décor was excellent, thoroughly mixing old with new. The food was good. The service was very good. The sushi was nice, excellent choices and pricing. The veggie fried rice was very good also. I was not impressed with the Pad Thai at all, very tasteless. The sea bass was good, the miso glaze helped with the taste, but did not permeate into the very large piece. The coconut sauce provided with the sea bass was not good. Overall a decent restaurant, I’d go back again.
