Restaurants near Chestertown Historic District

I really enjoyed date night here! Whoever they have playing the piano and singing on Friday nights is amazing. It really set the tone, and the service is top notch. I will definitely be back!

The Retriever has a cozy, comfortable atmosphere. The food is excellent. I had shucked oysters (on Special) and a fried chicken sandwich served with fries; my husband had clam chowder and a house burger with fries. The dining room is at the back of the building, set apart from the long bar, which was quite busy on a Thursday evening. There was a "buzz" in the air, but the room was not noisy at all. Highly recommended!

Our family's Christmas dinner experience at Chart House in Annapolis was incredible. The dinner was delicious and the service was impeccable. Our waiter made perfect recommendations regarding wine choices and dinner entrees and was attentive throughout our dining experience.

The staff was wonderful on Christmas Eve! Our server Julia was awesome and super accommodating. Elsa, the manager was very sweet and sent my wife an amazing dessert for her Birthday. We had a great time and the views from the upper level at Christmas were beautiful. There were some rowdy Christmas revealers at the bar but Elsa quieted them down. 😎 I highly recommend the restaurant for any occasion. We had a party of seven and everyone left very happy and satisfied.

Wonderful experience, enjoyed Birthday dinner with my son, knowledgeable staff, excellent service, stunning food and presentation. I look forward to returning to try other items.