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
- MMarkVIPBaltimore / Maryland •26 reviews4.0Dined 2 days agoI used to dine there weekly when I worked downtown 6 years ago. I have been twice in the past month and still enjoy the food and service.More infoTagliata RestaurantPrice: Expensive• Italian• Harbor East•4.7
- BBuckNew York City •1 review5.0Dined 4 days agoLauren, our server is terrific and a lot of fun.More infoThe Retriever Bar & The Decoy Bottle ShopPrice: Moderate• American• Chestertown•4.8
- AAliceWashington, D.C. Area •1 review5.0Dined 4 days agoIt’s a bustling busy place but the service is excellent as is the food. Great experience.More infoThe Choptank - AnnapolisPrice: Expensive• Seafood• Annapolis•4.6
- SSarahPhiladelphia County •8 reviews5.0Dined 4 days agoGreat view and the food, ambiance and service was outstanding.More infoRusty Scupper - BaltimorePrice: Expensive• Seafood• Inner Harbor•4.7
- WWesPhiladelphia County •1 review5.0Dined 5 days agoThe restaurant is located in a beautiful setting. The staff is very helpful without rushing us.More infoOsprey Point RestaurantPrice: Expensive• Contemporary American• Rock Hall•4.8
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Frequently asked questions
As of Jul 2, 2025 there is 1 restaurant in Chestertown. Filter by “outdoor dining”, “romantic” or “dog friendly”.
On OpenTable we support all cuisines. Find American and more. Use our filters to find exactly what you’re looking for and make your reservation today.
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.
Yes! OpenTable provides free, convenient and trusted options to book the best restaurants in Chestertown either on OpenTable or directly with the restaurant.
Yes, we partner with a third party to bring back menu information for restaurants near you.
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