1.Townofchestertown.com
Where Art, History and the Environment Meet. Chestertown, the county seat of Kent, the Eastern Shore of Maryland's oldest county, was founded in 1706 and served as a major port of entry during colonial times. Its brick sidewalks and attractive antique stores, restaurants and inns beckon visitors and residents alike to wander, browse and admire. A visit to Chestertown's Historic District is especially worthwhile, and includes a number of fine colonial residences, as well as some superb examples of later and more elaborate architectural styles.Second largest district of restored 18th-Century homes in Maryland, Chestertown is also home to Washington College, the nation's tenth oldest liberal arts college, founded in 1782.