Chestertown Restaurants
Make a free booking
Book for breakfast today in Baltimore / Maryland
Introducing OpenTable Icons
Book the city's award-winners, hot newcomers and hard-to-get tables.
Book the city's award-winners, hot newcomers and hard-to-get tables.
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
Explore dishes that diners are raving about
Restaurant experiences trending in Baltimore / Maryland
Frequently asked questions
As of 14 Mar 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 booking 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 takeaway.
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 retrieve menu information for restaurants near you.
Explore OpenTable
- Scott Point Marina
- Chester River Craft And Art School
- Brampton Bed and Breakfast Inn
- Green Point Marina
- Silver Heel Log Canoe
- Still Pond Historic District
- Kennersley Pointe Marina
- Clark's Conveniency
- Athey Field
- Urieville Park
- Kent Plaza Shopping Center
- Thornton
- Driftwood Inn
- Still Pond Station
- Shepherd's Delight
- Chestertown Railroad Station
- Roundtop Park
- Crestview Square Shopping Center
- Chestertown Historic District
- Pinkney Park