Chestertown in the County of Kent

Beautifully preserved National Register river town on Maryland's Eastern Shore whose architecture spans 300 years …

Chestertown, an Eastern Shore tidewater community founded in 1706, lies the county seat of Kent County, Maryland. Located in the arable countryside north of the Chesapeake Bay Bridge with a southern boundary formed by the placid Chester River, Chestertown is home to 4,500 residents. 

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 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, as it has for almost 250 years from its situation on the highest point in the natural terrain.

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, drink a drug-store fountain soda mixed to your pleasure, and take in a thoroughly modern rock ensemble. 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, 1.5 hours from Baltimore, Washington and Philadelphia. New York lies 3.5 hours away.