Chestertown Restaurants
Make a free reservation
Book for breakfast today in Baltimore / Maryland
Introducing OpenTable Icons
Book this year’s award-winners, hot newcomers, and hard-to-get tables.
Book this year’s award-winners, hot newcomers, and hard-to-get tables.
Great for Mother's Day Brunch
Restaurants available on May 10.
Restaurants available on May 10.
Experiences to celebrate mom
New restaurants to OpenTable in Baltimore / Maryland
Outdoor dining in Baltimore / Maryland
See what locals rave about in Chestertown
From verified diners like you
From verified diners like you
- KKwansmaBaltimore / Maryland •4 reviews5.0Dined 4 days agoI got ht filet mignon 9/10 (which was delicious!) my husband got the grilled lamb chops 9.5/10, and we split the sides of Mac and cheese 8/10, broccoli 10/10!!, and herb crusted fries 2/10 (too crispy). We also got the wagyu sliders 10/10!! and caviar tater tots 8/10 as appetizersMore infoThe Ruxton$$$$• Steakhouse• Harbor East•4.7
- LLeslieGoldWashington, D.C. Area •12 reviews5.0Dined 4 days agoThis was my first time at Tagliata for lunch and it did not disappoint. I had the Sicilian salad and calamari which were both amazing. Great service, beautiful patio setting.More infoTagliata Restaurant$$$$• Italian• Harbor East•4.8
- RrobertGoldWashington, D.C. Area •10 reviews5.0Dined 4 days agoThe best restaurant I’ve been to and I go out to eat often. Will be backMore infoAzumi$$$$• Japanese• Harbor East•4.6
- DdouglasWashington, D.C. Area •1 review5.0Dined 7 days agoI didn't mind driving the hour and forty minutes from Bethesda to "Sassafras". Nothing more calming than passing through Eastern Shore towns like Centerville and Chestertown and past all the beautiful farms. Greeted warmly at the restaurant and treated to 12 outstanding courses, ingredients all sourced locally, each with a story, expertly told by chef Paul Edward. Don't want to give away the menu details, but know that your experience will include favorites from the Chesapeake Bay and surrounds. Preparations were complex and included smoking, pickling, dry-aging, frying, grilling, purpose-built ovens, and everything is cooked in front of only eight lucky diners. Wine pairings are available and the cocktails were creative and yummy. Sassafras is worth a lengthy drive, one I expect to make on the regular.More infoSassafras$$$$• Seafood• Galena•4.9
- KKristinPhiladelphia County •4 reviews5.0Dined on May 1, 2026The wine and spirits list is AMAZING! The menu consists of classics and items which will expand your inner foodie. Highly recommend.More infoThe Retriever Bar & The Decoy Bottle Shop$$$$• American• Chestertown•4.9
Trending dishes in Chestertown
Explore dishes that diners are raving about
Restaurant experiences trending in Baltimore / Maryland
Private Dining
Find the perfect place for your next party or group dining event.
Explore private diningPrivate Dining
Find the perfect place for your next party or group dining event.
Frequently asked questions
As of May 9, 2026 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 Postmates, ChowNow, Olo, Toast, Uber Eats.
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
- Silver Heel Log Canoe
- Churchill Theatre-Community Building
- Crestview Square Shopping Center
- Bishopton
- Denton House
- Scott Point Marina
- Airy Hill
- Worton Creek Marina
- Wilmer Park
- Chestertown Historic District
- Pinkney Park
- Thornton
- Athey Field
- Urieville Lake Fish Management Area
- Kennersley Pointe Marina
- Quality Suites
- Buck Bacchus Store Museum
- Great Oak Manor
- Worton Regional Park
- Clark's Conveniency
- Home
- United States
- Baltimore / Maryland
