Historic Chestertown in the County of Kent on Maryland's Eastern Shore

       Chestertown was founded in 1706 on the broad Chester River and served as an important shipping hub for trade with England and between the colonies. The original Custom House still stands proudly on the River in its Historic District. There were important ties to Philadelphia as it was situated on the "road" to Annapolis and points South.  As the U.S. population center moved westward, Kent County settled into two hundred years of quiet agricultural and commercial fishing activities.  Very much as it is now. 

       Chestertown is home to a surprisingly large number of elegant, historic Georgian homes as well as Victorian “painted ladies.” With a population of 5,600, Chestertown is only an hour from Annapolis or Wilmington, about two hours from Baltimore, Philadelphia or Washington, and under four hours from New York City. 

       Washington College, founded in 1782, is located in Chestertown.  George Washington gave his  personal support to its founding and his permission to use his name.  It provides Chestertown a mix of athletic competitions, music and drama, adult education, and visiting speakers.  The town boasts a weekly Farmers Market, inviting shops, excellent coffee bars, restaurants, and art galleries—but no big box stores. The Chester River Yacht & Country Club offers a pool, an 18-hole golf course as well as a sailing program. The whole community supports major events like the annual Tea Party that comemorates a Revolutionary War protest; a Dickens Christmas Street Fair; and Down-rigging Weekend, when tall ships offer tours and sails on the Chester River. The strong arts and live theatre community adds to the vitality of this historic town. Today Chestertown is a vibrant mix of old families, newcomers, college students, full-time residents with children, and involved weekenders.  

       The County of Kent is primarily agricultural with thousands of acreage in conservation easements. Hunting, sailing and fishing dominate the outdoor activities. The small but vibrant Eastern Neck National Wildlife Refuge is located in the County.