In the 18th century, Chestertown was an important port in the colonial trade with London, until local patriots threw a cargo of dutiable tea overboard in 1774. Every year, locals celebrate the rebelliousness of their forebears with an annual Tea Party celebration.

Today, Chestertown is a vibrant, community with a thriving Arts and Entertainment district and a solid foundation in its historic roots. Chestertonians and visitors alike enjoy the sense of tradition and timelessness that the town emanates. Washington College, the liberal arts institution graced with its moniker by George Washington himself, contributes much to the intellectual sophistication of the town.

Within a few blocks from the waterfront docks, one can tour a 18th century customs house, sail on a reproduction schooner from the 1700’s, visit downtown galleries, shop in independently owned boutiques and dine in our friendly restaurants.  Neighbors and strangers greet each other casually on Chestertown’s brick-paved sidewalks. A deep, and obvious, Sense of Place pervades.

Chestertown is a swift 50-minute drive from Annapolis and Wilmington, 1.5 hours from Baltimore, Washington and Philadelphia. New York lies 3.5 hours away.

Useful Links
Calendar of Events