CHESTERTOWN is a quaint, historic, waterfront town nestled on the banks of the Chester River. As the county seat for rural bucolic Kent County, it offers a thriving downtown district, which includes Washington College, one of the oldest liberal arts colleges in the country, as well as our local hospital, Chester River Health System of the University of Maryland. Chestertown’s downtown offers live theater at the Garfield Center, a multitude of art galleries, fine dining and casual fare, eclectic shops featuring clothing, accessories, home decor, etc. Our bookshops cover the gamut from the latest in hardback to the very rarest of books.
On Saturday mornings the place to be is Fountain Park located in the center of town. The park is home to the nationally recognized Chestertown Farmers’ & Artisans’ Market. In addition, patrons may purchase fresh flowers, herb & garden plants, handmade soaps, fresh bread, homemade pies, etc. With the county’s three borders being the Chester River, the Sassafras River, and the Chesapeake Bay, there is water water everywhere creating activities from fun in the wide-open Bay to kayaking on the upper reaches of the watersheds. For more information on Chestertown and our surrounding towns, places and events, please visit the local links on this page.