Chestertown Restaurants
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Outdoor dining in Baltimore / Maryland
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From verified diners like you
From verified diners like you
- AashliGoldWashington, D.C. Area •7 reviews5.0Dined 2 days agoA fantastic experience at Flour & Wood at La Maison. From the flavorful pepperoni pizza and perfectly prepared prawns to the decadent tiramisu, every dish impressed. The expertly crafted cocktails elevated the entire meal. Looking forward to returning very soon.More infoFlour and Wood at La Maison$$$$• Pizzeria• Remington•4.8
- DDeacSouth Carolina •5 reviews5.0Dined 3 days agoThe food and service were outstanding. The menu offers a great variety in both food and beverage choices. We will most certainly be repeat diners when we next have the chance.More infoTagliata Restaurant$$$$• Italian• Harbor East•4.7
- KKristenAtlantic City / South Jersey Shore •1 review5.0Dined 3 days agoI loved everything about this restaurant. The food, ambience, service experience…it was all outstanding!More infoThe Ruxton$$$$• Steakhouse• Harbor East•4.7
- KKateSouth Carolina •1 review5.0Dined 6 days agoAn amazing experience! A surprising treat tucked away in Kent County!More infoSassafras$$$$• Seafood• Galena•5
- LLisaPhiladelphia County •13 reviews5.0Dined 6 days agoAlways great! The menu has expanded, Sugar Toast wings were great as well as the fish stew, both new menu items. Oyster were fantastic. Great shucking! The staff knows about the oysters. Katherine waited on us at the oyster bar. She was really good. People talk about the noise level but it’s a popular place, weekends draw college students. Super electric place with great food and service.More infoThe Retriever Bar & The Decoy Bottle Shop$$$$• American• Chestertown•4.5
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Frequently asked questions
As of Nov 6, 2026 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 Olo, Uber Eats, Toast, ChowNow, and Postmates.
Yes, you can also see restaurants near you offering takeout.
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Yes, we partner with a third party to bring back menu information for restaurants near you.
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- Chester River Craft And Art School
- Churchill Theatre-Community Building
- Crestview Square Shopping Center
- Buck Bacchus Store Museum
- Wilmer Park
- Chestertown Historic District
- Urieville Lake Fish Management Area
- Roundtop Park
- Green Point Marina
- Driftwood Inn
- Mystery Log Canoe
- Kibler Field
- Airy Hill
- Godlington Manor
- Holiday Inn Express Hotel & Suites Chestertown
- Charles Sumner Post No 25 Grand Army of the Republic
- Silver Heel Log Canoe
- Denton House
- Bishopton
- Thornton
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