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Chestertown Restaurants

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Book for breakfast today in Baltimore / Maryland

Great for Mother's Day Brunch

Restaurants available on May 10.
Restaurants available on May 10.

Experiences to celebrate mom

Outdoor dining in Baltimore / Maryland

See what locals rave about in Chestertown

From verified diners like you
From verified diners like you
  • Kwansma
    Baltimore / Maryland •4 reviews
    5.0
    Dined 4 days ago
    I 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 appetizers
    More info
    The Ruxton$$$$• Steakhouse• Harbor East
    4.7
  • LeslieGold
    Washington, D.C. Area •12 reviews
    5.0
    Dined 4 days ago
    This was my first time at Tagliata for lunch and it did not disappoint. I had the Sicilian salad and calamari which were both amazing. Great service, beautiful patio setting.
    More info
    Tagliata Restaurant$$$$• Italian• Harbor East
    4.8
  • robertGold
    Washington, D.C. Area •10 reviews
    5.0
    Dined 4 days ago
    The best restaurant I’ve been to and I go out to eat often. Will be back
    More info
    Azumi$$$$• Japanese• Harbor East
    4.6
  • douglas
    Washington, D.C. Area •1 review
    5.0
    Dined 7 days ago
    I didn't mind driving the hour and forty minutes from Bethesda to "Sassafras". Nothing more calming than passing through Eastern Shore towns like Centerville and Chestertown and past all the beautiful farms. Greeted warmly at the restaurant and treated to 12 outstanding courses, ingredients all sourced locally, each with a story, expertly told by chef Paul Edward. Don't want to give away the menu details, but know that your experience will include favorites from the Chesapeake Bay and surrounds. Preparations were complex and included smoking, pickling, dry-aging, frying, grilling, purpose-built ovens, and everything is cooked in front of only eight lucky diners. Wine pairings are available and the cocktails were creative and yummy. Sassafras is worth a lengthy drive, one I expect to make on the regular.
    More info
    Sassafras$$$$• Seafood• Galena
    4.9
  • Kristin
    Philadelphia County •4 reviews
    5.0
    Dined on May 1, 2026
    The wine and spirits list is AMAZING! The menu consists of classics and items which will expand your inner foodie. Highly recommend.
    More info
    The Retriever Bar & The Decoy Bottle Shop$$$$• American• Chestertown
    4.9

Restaurant experiences trending in Baltimore / Maryland

Frequently asked questions

As of May 9, 2026 there is 1 restaurant in Chestertown. Filter by “outdoor dining”, “romantic” or “dog friendly”.

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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.

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