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
- OTOpenTable DinerMontana •2 reviews5.0Dined 2 days agoWonderful atmosphere, great food and incredible service!More infoTagliata RestaurantPrice: Expensive• Italian• Harbor East•4.8
- KCKolaCWashington, D.C. Area •3 reviews5.0Dined 2 days agoMade reservations for 8:45 got there around 8:30 and was seated right away. The ambiance was amazing and the food was delicious. We will be returning again.More infoThe RuxtonPrice: Very Expensive• Steakhouse• Harbor East•4.8
- CChristianVIPWest Palm Beach •10 reviews5.0Dined 3 days agoSuper meal Neyah, thanks. You’ve got a great team. The meat loaf and pork dish were exceptional, as was the shrimp starter.More infoThe Retriever Bar & The Decoy Bottle ShopPrice: Moderate• American• Chestertown•4.8
- RRoccoWashington, D.C. Area •6 reviews5.0Dined 6 days agoEverything was great, will definitely go back, our waiter Dan was fantastic. Juan the bartender makes the best drinks!! More infoBygonePrice: Very Expensive• American• Harbor East•4.6
- OTOpenTable DinerBaltimore / Maryland •1 review5.0Dined 6 days agoI love the food,wine, and laughter with my family.More infoCooper's Hawk Winery & Restaurant - Annapolis, MDPrice: Moderate• American• Annapolis•4.5
Trending dishes in Chestertown
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Frequently asked questions
As of Mar 14, 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.
Explore OpenTable
- Brampton Bed and Breakfast Inn
- Holiday Inn Express Hotel & Suites Chestertown
- Churchill Theatre-Community Building
- Green Point Marina
- Silver Heel Log Canoe
- Kennersley Pointe Marina
- Still Pond Historic District
- Kirwan Meditation Garden
- Clark's Conveniency
- Athey Field
- Buck Bacchus Store Museum
- Urieville Park
- Still Pond Station
- Driftwood Inn
- Mystery Log Canoe
- Shepherd's Delight
- Urieville Lake Fish Management Area
- Roundtop Park
- Gobbler Hill
- Kings Town Park