Visitor Guide
Local Dining
Andy's
410-778-6779
337 1/2 High Street, Chestertown
Directions from Washington College
Restaurant and bar located on High Street offering live music, light fare and dinner.
Arby's
410-810-8955
707 Washington Avenue, Chestertown, MD
Directions from Washington College
Roast beef and chicken sandwiches, market fresh salads, curly fries, and shakes.
Bay Wolf - Rock Hall
410-639-2000
21270 Rock Hall Avenue, Rock Hall, MD
Directions from Washington College
Located in Rock Hall, the Bay Wolf offers American fare, seven days a week, for both lunch and dinner. Reservations and credit cards are accepted.
Bluebird Tavern
410-778-2885
512 Washington Avenue, Chestertown, MD
Directions from Washington College
A small area tavern offering burgers, fried foods, and diner-style lunches.
Blue Heron Café
410-778-0188
236 Cannon Street, Chestertown, MD
Directions from Washington College
Located just below the intersection of Cannon and Cross Streets, offers fine dining for both lunch and dinner. Reservations and credit cards are accepted. The Café is closed on Sundays.
Brooks Tavern
410-810-0012
870 High Street, Chestertown, MD
Directions from Washington College
A mix of rustic and hip. Reservations taken for parties of six or more. Brooks Tavern is closed on Sundays and Mondays.
Buzzie's
410-810-1992
205 Spring Avenue, Chestertown, MD
Directions from Washington College
Serves diner-style breakfast and lunch. It is located off Rt. 213 behind Royal Farms and Bennett's gas station.
Chessie's - Rock Hall
410-639-7727
21321 Rock Hall Avenue, Rock Hall, MD
Directions from Washington College
A dine-in and carryout restaurant, diners particularly enjoy the subs, steaks, and pizza at Chessie's, located in Rock Hall. Offering a sampling of other Italian specialties and American fare, their homemade ice cream, gelato, and water ice are extremely popular.
China House
410-778-3939
711 Washington Avenue, Chestertown, MD
Directions from Washington College
Located in Kent Plaza Shopping Center, offers Chinese cuisine.
Crossfire Cafe
410-778-0871
117 S. Cross Street, Chestertown, MD
Directions from Washington College
In the heart of downtown Chestertown, the Crossfire Cafe serves upscale food in a casual environment.
Domino's Pizza
410-810-3811
518 Washington Avenue, Chestertown, MD
Directions from Washington College
Offers take-out and delivery pizza.
Downey's
410-778-7128
713 Washington Avenue, Chestertown, MD
Directions from Washington College
Fried chicken, sundaes, and delicious milkshakes.
Dunkin' Donuts
410-778-6211
315 High Street, Chestertown, MD
Directions from Washington College
Offers donuts, coffee, and breakfast.
Durding's Store - Rock Hall
410-778-7957
5742 Main Street, Rock Hall, MD
Directions from Washington College
Quaint little country store with homemade ice cream.
Feast of Reason
410-778-3828
203 High Street, Chestertown, MD
Directions from Washington College
Restaurant serving gourmet soups, salads, and sandwiches, with dining room or take out. Feast of Reason is open for lunch only. It is located on lower High Street and is open until 6 p.m. or by reservation.
The Fish & Whistle
410-778-3566
98 Cannon Street, Chestertown, MD
Directions from Washington College
Overlooking the marina and the Chester River, the Fish and Whistle is opening soon.
The Granary - Georgetown
410-275-1603
79 George Street, Georgetown, MD
Directions from Washington College
Located on the Sassafras River about a twenty-minute drive north of Chestertown via Route 213. Overlooking a busy marina, this restaurant serves luncheon and dinner in a very pleasant, rustic ambiance. Reservations and credit cards are accepted.
Great Oak Landing
410-778-2100
22170 Great Oak Landing Road, Chestertown, MD
Directions from Washington College
Situated off of Fairlee Creek on the Upper Chesapeake Bay, Great Oak Landing serves traditional fare with Eastern Shore hospitality, daily, for lunch and dinner. Reservations and credit cards are accepted.
Harbor House
410-778-0669
23145 Buck Neck Road, Chestertown, MD
Directions from Washington College
Serves dinner only. In addition to the usual Eastern Shore seafood, it has some unusual specialties from around the world. Because of weekend crowds, it is wise to make a reservation. Credit cards are accepted. Ask for directions, as the location overlooking Worton Creek Marina is somewhat difficult to find the first time.
Harbor Shack - Rock Hall
410-639-9996
20895 Bayside Avenue, Rock Hall, MD
Directions from Washington College
Seafood, steak, and mexican waterfront bar and grill that offers great food, reasonable prices, live entertainment, and a unique atmosphere.
Herb's Soup and Such
410-778-9727
827 High Street, Chestertown, MD
Directions from Washington College
Great food on the go.
Hotel Imperial
410-778-5000
208 High Street, Chestertown, MD
Directions from Washington College
Offers fine dining in downtown Chestertown, only two blocks from the water. Call for reservations.
Jammin' Jesse's
410-778-3663
805 High Street, Chestertown, MD
Directions from Washington College
Take out or dine in. Subs and sandwiches.
KFC/Taco Bell
410-810-1399
709 Washington Avenue, Chestertown, MD
Directions from Washington College
Fried chicken or Mexican food served fast.
King Buffet
410-810-2080
Washington Square Shopping Center, Chestertown, MD
Directions from Washington College
An eat-in, buffet-style Chinese restaurant with a large selection of dishes.
Kitty Knight House - Georgetown
410-648-5200
14028 Augustine Herman Highway, Georgetown, MD
Directions from Washington College
Located on the Sassafras River, north of Chestertown. It serves traditional Eastern Shore dishes with colonial style hospitality. Reservations and credit cards are accepted.
Luisa's Café
410-778-5360
14 Washington Square, Chestertown, MD
Directions from Washington College
Restaurant located in the Washington Square plaza offering traditional Italian fare. Open seven days a week for lunch and dinner.
The Mainstay - Rock Hall
410-639-9133
5753 Main Street, Rock Hall, MD
Directions from Washington College
Description coming soon.
McDonald's
410-810-0163
875 Washington Avenue, Chestertown, MD
Directions from Washington College
Burgers, fries, shakes, or Happy Meals.
O'Connor's Pub
410-810-3338
844 High Street, Chestertown, MD
Directions from Washington College
Cozy Irish pub offering a variety of dinners and popular for its Wednesday Wing Nights.
Old Mill Bakery & Cafe
410-810-8841
207 S Cross Street, Chestertown, MD
Directions from Washington College
Located in downtown Chestertown on Cross Street. The Old Mill serves delicious gourmet foods and light fare, including lunch and take out dinners.
Old Oars Inn - Rock Hall
410-639-7858
5781 Main Street, Rock Hall, MD
Directions from Washington College
Description coming soon.
Osprey Point Restaurant - Rock Hall
410-639-2194
20786 Rock Hall Avenue, Rock Hall, MD
Directions from Washington College
A favorite among diners on the Eastern Shore, the restaurant at Osprey Point offers gourmet fare in a colonial setting. Dinner is served year round in addition to Sunday brunch. Reservations are recommended, and credit cards are accepted.
Pizza Hut
410-778-1070
213 N Crestview Square, Chestertown, MD
Directions from Washington College
Pizza, pasta, and salad bar. Dine-in or take-out.
Play It Again, Sam
410-778-2688
108 S Cross Street, Chestertown, MD
Directions from Washington College
Located on Cross Street in the historic district of Chestertown. The "meeting place" of locals, Play It Again Sam serves coffee and muffins plus much more.
Plaza Tapatia
410-810-1952
711 Washington Avenue, Chestertown, MD
Directions from Washington College
Traditional Mexican cuisine.
Procolino's Pizza and Italian Restaurant
410-778-5900
711 Washington Avenue #9, Chestertown, MD
Directions from Washington College
Restaurant located in Kent Plaza offering traditional Italian fare. Open seven days a week for lunch and dinner.
Rita's
410-778-0825
504 Washington Avenue, Chestertown, MD
Directions from Washington College
Cool down with many flavors of Italian ice, frozen custard, gelati, and mistos. Open 11 a.m. to 10 p.m.
Royal Farms (take out)
410-778-0646
301 South Maple Avenue, Chestertown, MD
Directions from Washington College
Subs, chicken, and more, 24/7.
Royal Farms (eat-in or take out)
410-778-3443
6502 Church Hill Rd, Chestertown, MD
Directions from Washington College
Subs, chicken, and more, 24/7.
Roma Pizza
410-810-3331
6346 Church Hill Road, Chestertown, MD
Directions from Washington College
Pizza, subs, and other Italian fare for take-out.
Stam Drugstore
410-778-3030
213 High Street, Chestertown, MD
Directions from Washington College
A classic American drugstore. Delicious milkshakes, ice cream, and fountain sodas.
Sweet Rick's Candy & Fudge Shop - Rock Hall
410-639-7700
5797 Main Street, Rock Hall, MD
Directions from Washington College
A chocolate lover's paradise!
Subway
410-778-5388
834 High Street, Chestertown, MD
Directions from Washington College
Offers sandwiches and salads.
** Student Discount **
10% off purchase with College ID.
Village Bakery & Café - Chestertown
410-810-1081
849 Washington Avenue, Chestertown, MD
Directions from Washington College
Great sandwiches and luncheon platters, plus homemade breads, cakes, pies, pasteries and donuts.
Village Bakery & Café - Galena
410-648-6400
119 N Main Street, Galena, MD
Directions from Washington College
Great sandwiches and luncheon platters, plus homemade breads, cakes, pies, pasteries and donuts.
Walley-Morris
410-810-3533
337 High Street, Chestertown, MD
Directions from Washington College
Stop in for lunch at one of Chestertown's newest dining establishments.
Waterman's Crab House - Rock Hall
410-639-2261
21055 Sharp Street, Rock Hall, MD
Directions from Washington College
Crab house with a laid back atmosphere.
Award Winning: Steamed Crabs, Jumbo Lump Crabcakes, BBQ Baby-back Ribs!
White Swan Tavern - Afternoon Tea
410-778-2300
231 High Street, Chestertown, MD
Directions from Washington College
Enjoy afternoon tea from at this historic colonial tavern.
300 Washington Avenue, Chestertown, Maryland 21620 | 410-778-2800 | 800-422-1782