Visitor Guide
Local Dining
Bay Wolf
410-639-2000 | Map
Located in Rock Hall; offers American fare for both lunch and dinner. Reservations accepted.
Bluebird Tavern
410-778-2885 | Map
A small area tavern offering burgers, fried foods, and diner-style lunches.
Blue Heron Café
410-778-0188 | Map
Located just below the intersection of Cannon and Cross Streets, offers fine dining for both lunch and dinner.
Brooks Tavern
410-810-0012 | Map
A mix of rustic and hip. Reservations taken for parties of six or more. Closed Sundays and Mondays.
Buzzie's
410-810-1992 | Map
Diner-style breakfast and lunch. It is located off Rt. 213 behind Royal Farms and Bennett's gas station.
Chessie's
410-639-7727 | Map
Dine-in and carryout subs, steaks, and pizza. Homemade ice cream, gelato, and water ice.
Feast of Reason
410-778-3828 | Map
Serves gourmet soups, salads, sandwiches. Dine in or take out. Mon.-Sat. 10-2:30 p.m.
The Granary
410-275-1603 | Map
On the Sassafras River; serves lunch and dinner in a rustic ambiance. Reservations accepted.
Great Oak Landing
410-778-2100 | Map
Serves traditional fare with Eastern Shore hospitality, daily, for lunch and dinner.
Harbor House
410-778-0669 | Map
Dinner only. Eastern Shore seafood and specialties from around the world.
Harbor Shack
410-639-9996 | Map
Seafood, steak, and Mexican waterfront bar and grill with live entertainment.
Hotel Imperial
410-778-5000 | Map
Offers fine dining in downtown Chestertown, only two blocks from the water. Call to reserve.
King Buffet
410-810-2080 | Map
An eat-in, buffet-style Chinese restaurant with a large selection of dishes.
Kitty Knight House
410-648-5200 | Map
Eastern Shore dishes served with colonial style hospitality. Reservations accepted.
Luisa's Café
410-778-5360 | Map
Offers traditional Italian fare. Open seven days a week for lunch and dinner.
O'Connor's Pub
410-810-3338 | Map
Cozy Irish pub offering a variety of dinners and popular for its Wednesday Wing Nights.
Osprey Point
410-639-2194 | Map
Gourmet fare in a colonial setting. Dinner year round, plus Sunday brunch. Call to reserve.
Play It Again, Sam
410-778-2688 | Map
The "meeting place" of locals, Play It Again, Sam serves coffee, muffins, and more.
Procolino's Pizza
410-778-5900 | Map
Restaurant located in Kent Plaza offering traditional Italian fare.
Rita's
410-778-0825 | Map
Many flavors of Italian ice, frozen custard, gelati, mistos. Open 11 a.m. to 10 p.m.
Stam Drugstore
410-778-3030 | Map
A classic American drugstore. Delicious milkshakes, ice cream, and fountain sodas.
Village Bakery
410-810-1081 | Map
Great sandwiches and luncheon platters, plus homemade breads, cakes, pies, and more.
