DINING

Cafes

Village Bakery & Cafe
849 Washington Avenue • Chestertown, MD 21620
410-810-1081
Fresh baked breads and pastries daily. They also serve breakfast, lunch, and dinner. more...

Andy's
337 1/2 High Street • Chestertown, MD 21620
410-778-6779
Enjoy eclectic live music all the time at this fun and relaxed restaurant. The menu features American food including salads, burgers, sandwiches, and steaks. They offer a large beer selection. more... map
Black-Eyed Susan
601 Washington Avenue • Chestertown, MD 21620
410-778-1214
Enjoy some of the finest regional cuisine. Serving lunch, dinner, and a Sunday brunch, in a relaxed atmosphere. Catering is also available. more... map
Dublin Dock Restaurant
12 Ericsson Avenue • Betterton, MD 21610
410-348-5896
Superb food, great hospitality, in a relaxed atmosphere offering burgers, sandwiches, and an extensive beverage menu. map
Hillside Seafood Market
2630 Centreville Road • Chestertown, MD 21617
410-758-2707
Enjoy a wide variety of seafood including clams, oysters, fish, and steamed crabs. Only a short ride from Chestertown. map
Kennedyville Inn
11986 Augustine Herman Highway • Chestertown, MD 21645
Located in Kennedyville
410-348-2400
Enjoy one of Chef Glenn May's delicious meals in a relaxing atmosphere with a regional cuisine consisting of both international and local ingredients from land and sea. There are two seperate banquet rooms available for any special event. more...
Play It Again Sam
108 Cross Street • Chestertown, MD 21620
410-778-2688
"Enjoy coffee by the cup or pound." A great spot for conversation, the paper, or just relaxing. Indoor and outdoor seating. map

Kettledrum Tea House
117 South Cross Street • Chestertown, MD 21620
410-810-1497
A unique tea house offering afternoon pastries and delicious dinners. They serve a multi-course tea meal presented on antique dishes and silver trays. After your tea enjoy browsing the gift shop where they offer beautiful imported tea pots and teawares. more... map