Chestertown Restaurants
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Outdoor dining in Baltimore / Maryland
See what locals rave about in Chestertown
From verified diners like you
From verified diners like you
- GGillianNew York City •7 reviews5.0Dined 1 day agoThe Retriever has a cozy, comfortable atmosphere. The food is excellent. I had shucked oysters (on Special) and a fried chicken sandwich served with fries; my husband had clam chowder and a house burger with fries. The dining room is at the back of the building, set apart from the long bar, which was quite busy on a Thursday evening. There was a "buzz" in the air, but the room was not noisy at all. Highly recommended!More infoThe Retriever Bar & The Decoy Bottle ShopPrice: Moderate• American• Chestertown•4.8
- AAugustBaltimore / Maryland •1 review5.0Dined 1 day agoThe food was absolutely amazing. We started with oysters, which were fresh and flavorful, and followed with a hearty bowl of seafood gumbo that was perfectly seasoned. For entrées, we tried the chicken mushroom linguine and the salmon—both dishes were cooked to perfection and bursting with flavor. Our waiter was attentive and honest, even mentioning that the bar service was a bit slow that evening. To make up for it, they graciously offered us a complimentary dessert. While the gesture was unnecessary, it was certainly appreciated and capped off an already stellar meal. The combination of exceptional food and thoughtful service made this an unforgettable dining experience. I’ll definitely be back!More infoRye Street TavernPrice: Expensive• American• Port Covington•4.5
- SSusanBaltimore / Maryland •1 review5.0Dined 2 days agoOur family's Christmas dinner experience at Chart House in Annapolis was incredible. The dinner was delicious and the service was impeccable. Our waiter made perfect recommendations regarding wine choices and dinner entrees and was attentive throughout our dining experience.More infoChart House Prime - AnnapolisPrice: Expensive• Seafood• Annapolis•4.6
- NNormanBaltimore / Maryland •2 reviews5.0Dined 3 days agoWonderful experience, enjoyed Birthday dinner with my son, knowledgeable staff, excellent service, stunning food and presentation. I look forward to returning to try other items.More infoCooper's Hawk Winery & Restaurant - Annapolis, MDPrice: Moderate• American• Annapolis•4.4
- GGregVIPWashington, D.C. Area •7 reviews5.0Dined 3 days agoGreat as always! Great food and great service! I’ll see you back in a few weeks!More infoTagliata RestaurantPrice: Expensive• Italian• Harbor East•4.8
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Frequently asked questions
As of Dec 27, 2024 there is 1 restaurant in Chestertown. Filter by “outdoor dining”, “romantic” or “dog friendly”.
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Yes! We partner with restaurants in Chestertown who deliver with Toast, Postmates, Uber Eats, Olo, ChowNow.
Yes, you can also see restaurants near you offering takeout.
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Explore OpenTable
- Worton Creek Marina
- Scott Point Marina
- Chester River Craft And Art School
- Denton House
- Green Point Marina
- Still Pond Historic District
- Bishopton
- Quality Suites
- Buck Bacchus Store Museum
- Driftwood Inn
- Urieville Park
- Chestertown Historic District
- Worton Regional Park
- Chestertown Railroad Station
- Urieville Lake Fish Management Area
- Great Oak Club And Golf Course
- Carvill Hall
- Crestview Square Shopping Center
- Pinkney Park
- Kibler Field