Chestertown Restaurants
Make a free reservation
Book for breakfast today in Baltimore / Maryland
View all
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.
Great for Mother's Day Brunch
View all
Experiences to celebrate mom
Outdoor dining in Baltimore / Maryland
View all
See what locals rave about in Chestertown
From verified diners like you
From verified diners like you
- DdevonVIPBaltimore / Maryland •9 reviews5.0Dined 2 days agoLove it here! The best experience and really yummy foodMore infoThe Retriever Bar & The Decoy Bottle ShopPrice: Moderate• American• Chestertown•4.9
- MMarionWashington, D.C. Area •2 reviews5.0Dined 4 days agoThe food was absolutely delicious. The service was timelyMore infoThe RuxtonPrice: Very Expensive• Steakhouse• Harbor East•4.7
- AAdamaWashington, D.C. Area •6 reviews5.0Dined 4 days agoI had my birthday dinner here and the service was amazing! The view of Baltimore city was amazing too! The food on a scale was 8/10.More infoBygonePrice: Very Expensive• American• Harbor East•4.6
- CcliffVIPWashington, D.C. Area •11 reviews5.0Dined 7 days agoAs always the staff at Osprey Point make it a wonderful experience - no matter how crowded it gets they stay cheerful and helpful. It doesn’t hurt that the food I good as well!More infoOsprey Point RestaurantPrice: Expensive• Contemporary American• Rock Hall•4.8
- BBrentCincinnati / Dayton •1 review5.0Dined on Apr 18, 2025Fantastic service and atmosphere once again. Food was delicious, staff was very friendly and it was a perfect way to celebrate our anniversary. Highly recommend!More infoTagliata RestaurantPrice: Expensive• Italian• Harbor East•4.7
Trending dishes in Chestertown
Explore dishes that diners are raving about
Restaurant experiences trending in Baltimore / Maryland
Frequently asked questions
As of Apr 27, 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
- Widehall
- Chester River Craft And Art School
- Churchill Theatre-Community Building
- Green Point Marina
- Silver Heel Log Canoe
- Still Pond Historic District
- Crumpton Auction
- Kirwan Meditation Garden
- Clark's Conveniency
- Athey Field
- Buck Bacchus Store Museum
- Still Pond Station
- Driftwood Inn
- Wilmer Park
- Urieville Park
- Shepherd's Delight
- Crestview Square Shopping Center
- Gobbler Hill
- Kings Town Park
- Pinkney Park