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  3. Baltimore / Maryland
  4. Eastern Shore
  5. Chestertown

Best Cocktail Bars in Chestertown

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19 restaurants available nearby

How are Featured results ranked

A photo of Order of the Ace restaurant
5.0
Exceptional(72)
$$$$
• Cocktail Bar • Harbor East
Booked 23 times today
Great intimate spot that reminds me of a speakeasy. Really appreciate the live music. The intimacy is what makes this place a little gem in East Harbor.
A photo of Fogo de Chão - Baltimore restaurant
4.0
Excellent(4665)
$$$$
• Cocktail Bar • Inner Harbor
Booked 89 times today
My Significant Other and I loved it. It was her first time and she loved it every single bite. We left bellies full 😋😋
A photo of Harold Black - Annapolis restaurant
4.6
Exceptional(101)
$$$$
• Cocktail Bar • Annapolis
Booked 18 times today
Incredible service - lovely evening and perfect locale for the start of a girls night out!
A photo of Seasalt Annapolis restaurant
4.6
Exceptional(429)
$$$$
• Cocktail Bar • Annapolis
Booked 36 times today
The meal was better than we thought, the Ribeye exceptional, but the carrots were the best. The wait staff made my wife feel very special, and she is, it was nearly a perfect meal and experience for the two us. I am looking forward to going again as soon as we can. Wonderful dining . On a side note the hostess and her elder sister were out servers and we cannot compliment them enough, very attentive, but not overerally so.
A photo of Level Small Plates Lounge restaurant
4.3
Awesome(2329)
$$$$
• Cocktail Bar • Annapolis
Booked 16 times today
Excellent choice of menu options. All were very well prepared and enjoyable. Looking forward to returning.
A photo of Bardea Steak restaurant
4.6
Exceptional(1219)
$$$$
• Cocktail Bar • Wilmington
Booked 30 times today
As usual, everything, from ambiance, to service, to food was excellent.
A photo of Fogo de Chão - Towson restaurant
4.2
Awesome(587)
$$$$
• Cocktail Bar • Towson
Booked 73 times today
We will continue to come back here every month , love this place
A photo of Dutch Courage restaurant
4.6
Exceptional(619)
$$$$
• Cocktail Bar • Charles Village
Booked 23 times today
Food was lovely, staff was so nice (sent complimentary prosecco for my birthday 🥹) and drinks were so fun!!
A photo of Miracle at 34 Market Place Holiday Pop Up restaurant
3.6
Very Good(78)
$$$$
• Cocktail Bar • Downtown
Cute and kitschy! A must visit for a holiday outing.
A photo of One Eleven Main restaurant
4.9
Exceptional(1643)
$$$$
• Cocktail Bar • Bel Air
Booked 8 times today
Great food, service and setting! Thankful to have a spot like this in Bel Air.

See what locals rave about

From verified diners like you
From verified diners like you
  • Ryan
    Las Vegas •1 review
    5.0
    Dined 3 days ago
    The meal was better than we thought, the Ribeye exceptional, but the carrots were the best. The wait staff made my wife feel very special, and she is, it was nearly a perfect meal and experience for the two us. I am looking forward to going again as soon as we can. Wonderful dining . On a side note the hostess and her elder sister were out servers and we cannot compliment them enough, very attentive, but not overerally so.
    More info
    Seasalt Annapolis$$$$• Seafood• Annapolis
    •
    4.6
  • Dawn
    Baltimore / Maryland •1 review
    5.0
    Dined 7 days ago
    Great food, service and setting! Thankful to have a spot like this in Bel Air.
    More info
    One Eleven Main$$$$• American• Bel Air
    •
    4.9
  • JohnGold
    Baltimore / Maryland •2 reviews
    5.0
    Dined on 21 Oct 2026
    Excellent choice of menu options. All were very well prepared and enjoyable. Looking forward to returning.
    More info
    Level Small Plates Lounge$$$$• American• Annapolis
    •
    4.3
  • Mezz
    1 review
    5.0
    Dined on 14 Oct 2026
    My Significant Other and I loved it. It was her first time and she loved it every single bite. We left bellies full 😋😋
    More info
    Fogo de Chão - Baltimore$$$$• Steakhouse• Inner Harbor
    •
    4
  • Purvis
    Baltimore / Maryland •13 reviews
    4.0
    Dined on 8 Oct 2026
    Great intimate spot that reminds me of a speakeasy. Really appreciate the live music. The intimacy is what makes this place a little gem in East Harbor.
    More info
    Order of the Ace$$$$• Cocktail Bar• Harbor East
    •
    5
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