Founded in 1706, Chestertown is a historic, picturesque town along the banks of the Chester River. Downtown Chestertown offers charming historic homes on quiet, tree-lined streets. Residents can find newer homes, condos, and waterfront communities in nearby developments. In the surrounding areas of Kent County, you'll find historic gentleman's farms and lovely waterfront properties.

 

There is a thriving art and entertainment community, including the popular "Music in the Park" Summer Concerts. Chestertown is also home to Washington College, the nation's tenth oldest liberal arts college.