"Life at its best."

Our Area

Welcome to historic Main Street Chestertown, a quaint, colonial, waterfront town nestled on the banks of the Chester River that traces its roots back to the mid-seventeenth century.  As the county seat for rural, bucolic Kent County, it offers a thriving downtown district, which includes Washington College, one of the oldest liberal arts colleges in the country, as well as our local hospital, Chester River Health System of the University of Maryland. Chestertown’s downtown offers live theater at the Garfield Center, a multitude of art galleries, fine dining as well as casual fare, eclectic shops featuring clothing, accessories, home décor and much more. Our cafes and bookshops allow for casual coffee and conversation.

On Saturday mornings we meet at Fountain Park located in the center of town. The park is home to our nationally recognized Chestertown Farmers’ & Artisans’ Market where patrons may purchase fresh flowers & produce, herb & garden plants, handmade soaps, fresh bread, homemade pies and many other locally crafted products.

Chestertown and the surrounding region hold a seemingly endless array of both land and water recreation. Washington College’s 1782 Society offers activities ranging from sailing and rowing clubs to a modern fitness facility that includes swimming and tennis. An eighteen hole golf course is located just minutes down the road at Chester River Yacht and Country Club. 

Furthermore, the region surrounding this property offers numerous choices, from cruising and fishing the open waters of the Chesapeake to countless miles of estuaries for canoeing and kayaking. ShoreRivers is a wonderful organization to learn more about our Chester River.

Aerial photo of Downtown Chestertown by Shore Studios.

Chestertown is uniquely situated approximately 90 minutes from the three major metropolitan areas of Washington, Baltimore, and Philadelphia and a short 45 minutes from historic Annapolis.

Chestertown, Maryland, United States