Chestertown and the surrounding area has a wonderful selection of good restaurants. Below is a list of those that our guests enjoy. Please, do not hesitate to contact us by e-mail or by telephone 1-866-305-1860 if you need help deciding on a good place or would like for us to make a reservation for you. We are here to help.
We have added links to the restaurants that have a web-site.
Blue Heron Cafe
Consistently one of the best restaurants in town. Sophisticated regional American cuisine, served in a pleasant atmosphere. The oyster fritter is awesome! Open for dinner Monday through Saturday. Reservations a must on weekends. 236 Cannon Street, Chestertown - 410-778-0188
Brix Tapas kitchen and wine cellar. This is Chestertown's newest eatery and although they had a very nice start the feedback has been a bit mixed lately. 337 High Street, Chestertown 410-810-2749
Brook's Tavern
This casual restaurant is housed in a restored old mill and is simply awesome. The food is imaginative, beautifully presented, and the restaurant is less than a mile from the inn. They only take reservations for six and more. 870 High Street, Chestertown 410-810-0012
Fish Whistle
The "Old Wharf" has new owners, a new name and a nice new menu. It's the only waterfront restaurant in Chestertown and a good place for a casual meal. Our guests have been delighted with their meals and the service. At the end of Cannon Street. 410-778-3566
Harbor House
This waterfront restaurant is a bit out of the way in Worton, about a 15 minute drive from the inn. Our guests have been raving about it. They are open 7 days a week during the summer. 23145 Buck Neck Road, Chestertown
Waterman's Crabhouse
In the old Eastern Shore tradition, crabs, cold beer and live music on weekends. Need I say more? It is the restaurant with the best sunsets. Open 7 days a week Memorial Day through the end of October. Sharp Street Wharf, Rock Hall 410-639-2261
Lunch and lighter fare
Durding's Store
Old-fashioned soda fountain and ice cream parlor on Rock Hall's Main Street. Definitely worth a stop. Main Street, Rock Hall 410-778-7957
Herb's Soup & Such
Top-notch take-out food. Fresh, local ingredients, nicely prepared. Open Monday through Friday for breakfast and lunch, 7:30 to 3 p.m. 827 High Street, Chestertown 410-778-9727
Play It Again Sam's Coffeehouse
Besides Scottie's Shoe Store this is the best place to brush up on local gossip. They also serve great espresso, cappuccino and a limited lunch menu which can be enjoyed al fresco. 108 S. Cross Street, Chestertown 410-778-2688
