Founded in 1706, Chestertown rose in stature when it was named one of the colony’s six Royal Ports of Entry. The shipping boom that followed this designation made the town at the navigable head of the Chester River wealthy. Chestertown is also home to Washington College, founded in 1756. In the mid-18th century, Chestertown trailed only Annapolis as Maryland’s leading port. Due mainly in part to its regional severance from the growing Baltimore and Washington, DC metropolitan corridor, over the next two centuries the town and surrounding region experienced very little growth and subsequently its historic character remained almost perfectly preserved until the mid-20th century.