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, the Chester River Health System of the University of Maryland. Chestertown’s downtown offers live theater at the “Prince,” a multitude of art galleries, and eclectic shops. Our three 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 which is located in the center of town. The park is home to the nationally recognized Chestertown Farmers Market which draws local produce along with locally grown and grass-fed beef, pork, lamb, and eggs. In addition, patrons may purchase fresh flowers, handmade soaps, and various arts and crafts. 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 gunk holing in a back “crick.”  For more information on Chestertown and our surrounding towns, places and events, please visit the local links on this page.