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Chestertown (Maryland)

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Chestertown (Maryland)

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Chestertown is in Maryland's Eastern Shore. Chestertown, the county seat of Kent, the Eastern Shore of Marylands's oldest county, was founded in 1706 and served as a port of entry during colonial times. A town rich in history, its attractions include a blend of past and present. Its brick sidewalks and attractive antique stores, restaurants and inns beckon visitors and residents alike to wander through the historic district and enjoy homes and places with architecture ranging from the Georgian mansions of wealthy colonial merchants to the elaborate style of the Victorian era. Chestertown is situated on a scenic peninsula where the Chester and Sassafras rivers meander into Chesapeake Bay.

Get in

Get around


  • Chestertown Famers' Market

Chestertown Farmers Market is located on Park Row in the heart of downtown Chestertown at 118N Cross Street. It is open every Saturday morning from the first Saturday in April until the last Saturday before Christmas. The market includes a variety of produce as well as meats, cheeses, soaps and lotions, and baked goods.

  • Washington College

Washington College is located in Chestertown. Washington College is a private liberal arts college that has roughly 51% in state students and 49% out of state students. The college was founded in 1782 and is the tenth oldest college in the United States.

  • Visit the Chester River

The Chester River can be easily accessed by going all the way down high street, passing the Imperial Hotel on the left.

  • First Friday

The first Friday of each month, many stores in the downtown area pariticpate in what is known as "First Friday". Participating stores and gallerys extend their hours for gallery viewing and shopping.





Play it Again Sam's (108 South Cross St) is the towns only coffee shop offering fresh brewed coffee, tea, pastries and some hand selected wine for sale by the bottle. You're likely to be in line next to some Washington College students and professors or the regulars around town. Many out of towners consider this a near perfect coffee shop!


  • Great Oak Manor 10568 Cliff Road, Tel (800) 504-3098. [1] This bed and breakfast is ideal for secluded getaways to the Chesapeake Bay area. Far from any highway or large towns, our inn will relax you with the sounds of nature, the aura of yesteryear, and the comforts of modern society.
  • The Imperial Hotel located at 208 High Street is a hotel that is popular with the locals as well as tourists. Built in 1903, the Imperial Hotel has become a significant landmark in Chestertown and a must-see for many tourists. The Front Room Restaurant serves lunch and dinner Tuesday through Saturday and brunch on Sunday. The hotel has 11 rooms and 2 suites. Something unique about the Imperial Hotel is that each room has its own individual interior, furnised with authentic period furnishings and antiques. The Imperial Hotel's website:

Get out

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