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...

Locally Operated

• 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

• Chessie's Restaurant and Carryout
  21325 Rock Hall Avenue, Unit 2 • Rock Hall, MD 21661
  In the New Yarmouth Plaza
  410-639-7727
  A popular pizza restaurant, Chessie's also offers pasta, sandwiches, entrees, and homemade ice cream. Carryout is 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...

• Pasta Plus Restaurant
  21356 Rock Hall Avenue • Chestertown, MD 21661
  410-639-7916
  A family atmosphere offering great food including cheese steaks, subs, pizza, soups, and salads. Open seven days a week for breakfast, lunch, and dinner. more...  map

• 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

• Waterman's Crab House
  21055 Sharp Street • Rock Hall, MD 21661
  Located 12 miles away in Rock Hall
  410-639-2261
  Eat on the dock at this great restaurant offering award winning steamed crabs, jumbo lump crabcakes, and bbq ribs. There is live entertainment on the weekends and dockage slips for anyone arriving on boat. Open seven days a week at 11 a.m. Full service menu. 2008 Best of the Bay steam crabs, crabcakes, family restaurant, and most romantic.  map

Tea Rooms

• 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