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Roast beef sandwiches and more in a quick, convenient manner.
Good homecooking! Breakfast all day, everyday! Also, lunches and home-made desserts.
As featured in Time Magazine, the restaurant serves regional American fare with Eastern Shore touch. Home of the Oyster fritter. Reservations recommended for weekends and parties of 5 or more.
Great food and recreation in a convenient meeting place in Chestertown.
Proudly serving Chestertown for over 30 years! Exclusively serving Boar's Head in the deli. Soups and salads are also available.
Serving sushi and authentic Thai cuisine.
Chester River Wine & Cheese Co. is a retail store specializing in wine, cheese, olives, cured meats, pate, and other gourmet specialty provisions. We also offer wine by the glass, cheese and charcuterie boards for onsite consumption.
Authentic Chinese food to eat-in or carry out.
Domino's pizza made and delivered fresh every day!
Something fresh is always brewing here!
Local gathering spot for friends and great food!
Evergrain Bread Company specializes in artisan breads and pastries crafted in the European tradition.
Chestertown's only waterfront restaurant overlooking the Chester River at the foot of Cannon Street.
Home of the "Big Freeze Burger" Burgers, Fast Food, Sandwiches, Coke products. Improved Ice Cream: sundaes, shakes, cones etc. Fried Chicken, Burgers, Steaks, Fries
Proudly serving Dietz & Watson premium meats and artisan cheeses on all subs, sandwiches and paninis. Also selling Dietz & Watson freshly sliced meats and cheeses by the pound. Soups, sides and desserts are house-made, in-store. Also offering...
Enjoy our tasty cocktails, food, and live music on the stage and in the piano bar. Carryout available.
Famous Kentucky Fried Chicken specialties along with favorites from Taco Bell
Chinese food served in a buffet setting.
The Kitchen at the Imperial provides an award winning casual fine dining restaurant experience, in a unique, upscale atmosphere. Chef Steve Quigg (winner, Best Chef on the Eastern Shore 3 years in a row) and his staff pride themselves on their farm..
Voted best restaurant in Chestertown by TripAdvisor. Serving breakfast, lunch and dinner. American Cuisine with a twist. Some Eastern Shore Classics and some neat dishes with a twist.
Serving lunch and dinner daily, featuring Italian specialty entrees, gourmet pizzas and sandwiches in a casual dining atmosphere. Our dishes are prepared with locally grown fresh ingredients. Dine-in or carry out.
Enjoy a casual dinner over looking Fairlee Creek. You can sit inside or outside on the covered deck. Traditional Eastern Shore cuisine, sandwiches, and light appetizers.
Traditional McDonald's sandwich, salad and specialty menu in a fast-food setting. Free WiFi
Family friendly Irish style Pub and restaurant with an enclosed outdoor dining area during the summer, offering both traditional and local favorites.
Pizza Hut: Serving America's favorite pizza and Italian specialities.
Located in the heart of downtown Chestertown, Play It Again Sam serves a complete line of coffee offerings, breakfast and lunch specialties, snacks and wine.
Serving your favorite Mexican and South of the Border specialties daily.
Great deli sandwiches and fresh cut steaks and meat.
Serving Kent County's favorite pizza and Italian specialties.
Rita's Ice-custard happiness. Serving Italian ice and other cool treats!
Open March 5th - September 30th
Deli, salads, milk, coffee, soda and Convenience store.
Stam's is serving soda fountain favorites and ice cream treats.
Subway serves made-to-order sandwiches and subs. Breakfast served daily.
We offer a full service menu. Our restaurant has long had a reputation for the best crab cakes on the Bay. Seasonal operation.
All-natural smoothies made with 100% fresh fruit, yogurt, and choice of milk. Gluten-free and dairy-free options available.
Uncle Charlie's Bistro offers a full lunch and dinner menu, as well as weekly specials featuring the finest cuisines offered on Maryland's Eastern Shore.
Museum quality restoration of Historic Colonial Inn, operating as Bed and Breakfast, and serving afternoon tea, in the heart of Chestertown's Historic District.