Chestertown, the seat of Kent County—the Eastern Shore’s oldest county— represents small town life at its best. Located on the Chester River, it lies within easy driving distance of Annapolis, Baltimore, Washington, D.C., and Philadelphia. The town of 4,000 boasts a rich heritage as an important grain and tobacco port, a prominent Episcopal parish, and, later in the 18th century, the home of citizens who played leading roles in state and national affairs. On May 3, 1774, they boarded the brigantine Geddes, lying at anchor in the Chester River, and tossed its cargo of tea overboard in protest against the British tea tax—a statement of conviction that mirrored the actions of their Boston brethren in the same year. Nowadays, on Memorial Day weekend a parade commemorates the Chestertown Tea Party.

In 1782, General George Washington wrote, “I am much indebted for the honor conferred on me by giving my name to the College at Chester.” Washington College, the liberal arts college that he helped to establish with a gift of 50 guineas still flourishes in Chestertown, where it is cherished as a vital asset to the cultural life of the entire region.

In recent years, Chestertown’s architectural history has received well deserved attention. An intensive movement aimed at preserving the town’s authentic Colonial homes and a resurgence of interest in its many Victorian structures have resulted in the restoration of many of the town’s worthy 18th- and 19th-century buildings.

Today’s Chestertown is more than a museum. It is a center of economic, social, recreational, and tourism activity. It boasts exemplary public and private schools, attractive neighborhoods, and a citizenry that is ever active in directing the course of its town and in welcoming visitors to enjoy the results with them.