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Fine dining
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 lunch and dinner Monday through Saturday. Reservations a must. 236 Cannon Street, Chestertown - 410-778-0188
Crossfire Cafe
Chestertown's newest addition to fine dining. Entrees range from roasted organic salmon to kobe beef to vegetarian entrees. Open for lunch Monday and Thursday through Saturday from 11:30 - 2:30 for lunch, and 5:30 - 8:30 for dinner. Brunch served on Sundays. Reservations required. 117 S. Cross Street, Chestertown. 410-778-0871.
The Front Room at The Imperial Hotel
This "top of the crop" restaurant has a very creative menu. The food is excellent and nicely presented. A special occasion restaurant, for sure! Open for dinner Wednesday through Saturday. Reservations a must. 208 High Street, Chestertown - 410-778-5000. Read Innkeeper dining review
Casual Dining
Brook's Tavern
This casual restaurant is housed in a restored old mill and is simply awesome. Can you tell that it is the innkeeper's favorite place to eat? The food is imaginative, beautifully presented, and the restaurant is only ½ mile from the inn. They take reservations for parties of 6 and more only. 870 High Street, Chestertown 410-810-0012
Reiley's on the River temporarely out of commission. We'll let you know when they open up again.
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, Coffee, Ice Cream and Night Caps
Andy's
A wonderful bar in the heart of historic Chestertown. Great live music on weekends. They serve the best bar food until late in the evening; now also open for lunch Wednesday through Saturday. Closed Sundays. 337 High Street, Chestertown - 410-778-6779
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
Feast of Reason
Good choice for lunch. This casual place serves imaginative sandwiches, soups and quiches. Open Monday through Saturday. 203 High Street, Chestertown - 410-778-3828
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
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