Chestertown Restaurants
Make a free reservation
Book for dinner 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
- NNickBaltimore / Maryland •2 reviews4.0Dined 1 day agoService was excellent, very attentive. Very expensive for the amount of food. We went on Valentines weekend, were not able pick off a menu which we didn’t know until seated. $90 a person which didn’t not include a drink or desert. Quality was good. All in all nice place but don’t go for a value, not there!More infoOsprey Point RestaurantPrice: Expensive• Contemporary American• Rock Hall•4.9
- GGillianNew York City •9 reviews5.0Dined 3 days agoThe cozy dining room at the rear of this popular bar is a great place to enjoy a meal. We recently dined on shucked oysters, deviled eggs, oyster sliders, and a smashburger with fries. Everything was excellent.More infoThe Retriever Bar & The Decoy Bottle ShopPrice: Moderate• American• Chestertown•4.8
- WWilliamBaltimore / Maryland •2 reviews5.0Dined 3 days agoStaff was amazing, the food for our first time there was amazing taste. The drink I had for Valentines was amazing, reminded me of an old fashioned!!! Can't wait to returnMore infoTagliata RestaurantPrice: Expensive• Italian• Harbor East•4.8
- DDr . NatalieVIPWashington, D.C. Area •7 reviews5.0Dined 3 days agoCame to celebrate a birthday . The table we were sated at was nice . The parties sprung us however made the experience very unpleasant. Additionally having the runner continually ask if I was done or take my plate was not only an annoyance but felt invasive as if I was being rushed out of the establishment. I would give a 4/5 as our server was excellent ( crystal ) but I do believe further training is needed for the runners as no where in the reservation did it indicate a time allotment for me dining ( e.g. 3 hour window or 2 hour max ). It made the evening very uncomfortable and unpleasant to say the least .More infoBygonePrice: Very Expensive• American• Harbor East•4.6
- BBrianVIPBaltimore / Maryland •22 reviews5.0Dined 7 days agoMy wife and I had the pleasure of dining at The Ruxton on a random Monday night, and it turned into an unforgettable experience. We went with a mix of appetizers—grilled oysters, potato gnocchi in sage brown butter with goat cheese, Wagyu beef sliders, and king crab cocktail. It was a completely random selection, but every dish was outstanding. The gnocchi was rich and perfectly balanced, the Wagyu sliders were incredibly flavorful, and the king crab was fresh and sweet. All of it was complemented beautifully by a fantastic Sancerre. What truly elevated the evening, though, was our server, Sammy. Not only did Sammy provide exceptional service, but we also had a great conversation throughout the night. Engaging, knowledgeable, and genuinely friendly, Sammy made the experience even more memorable. It’s rare to have such a combination of incredible food and outstanding hospitality. I’ll definitely be returning—and when I do, I’ll be asking for Sammy!More infoThe RuxtonPrice: Very Expensive• Steakhouse• Harbor East•4.8
Trending dishes in Chestertown
Explore dishes that diners are raving about
Restaurant experiences trending in Baltimore / Maryland
Frequently asked questions
As of Feb 17, 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 retrieve menu information for restaurants near you.
Explore OpenTable
- Airy Hill
- Scott Point Marina
- Widehall
- Island Image Log Canoe
- Chester River Craft And Art School
- Holiday Inn Express Hotel & Suites Chestertown
- Silver Heel Log Canoe
- Still Pond Historic District
- Athey Field
- Driftwood Inn
- Urieville Park
- White House Farm
- Shepherd's Delight
- Urieville Lake Fish Management Area
- Great Oak Club And Golf Course
- Roundtop Park
- Carvill Hall
- Kings Town Park
- Pinkney Park
- Godlington Manor