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.
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!
The Imperial Inn 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: http://www.imperialchestertown.com/index.html