Golf in Chestertown

Chestertown is Kent County's elegant colonial port town on the Chester River, arguably the best-preserved eighteenth-century streetscape on the Eastern Shore. Washington College—Maryland's oldest college, chartered in 1782 with George Washington's permission and financial support—anchors the town's academic and cultural life. The Mears Great Oak Landing Marina incorporates golf among its waterfront recreational amenities, fitting the Eastern Shore tradition of leisure facilities clustered around navigable waterways. Chestertown's combination of architectural preservation, waterfront access, and small-college energy makes it one of the most appealing communities in Maryland for visitors seeking authenticity over resort gloss. Kent County's agricultural landscape of grain and soybean farms frames the town's colonial-era streetscape with a rural context that has changed little since the nineteenth century.