Chestertown, Maryland

Chestertown is the most historically significant and oldest of the small towns in Maryland’s eastern peninsula. The National Trust for Historic Preservation has named Chestertown as one of America’s Dozen Distinctive Destinations. Founded in 1706, Chestertown rose in stature and wealth when it was named one of the colony's six Royal Ports of Entry. A burgeoning merchant class infused riches into the town, reflected in the many brick mansions and townhouses that are enjoyed by today's residents and visitors. Chestertown is second only to Annapolis in the number of 18th century homes. The town is home to Washington College, a private liberal arts college founded in 1782. It is the tenth oldest college in the United States and George Washington was a founding patron.