Resources for Retiring in Chestertown, Maryland

Chestertown, Maryland, is located along the Chester River, a major tributary of the Chesapeake Bay, in a region known as the Eastern Shore. The town serves as the county seat of Kent County, the oldest county in the state. Chestertown’s history dates back to the founding in 1706 when the city served as one of England’s primary Royal Ports of Entry. These historical roots are seen today by the city’s brick sidewalks, eclectic antique stores, traditional-style inns, and houses sporting architecture reminiscent of colonial times. Visitors and residents can’t help but feel a sense of nostalgia as they venture down the same streets once trodden by the early colonial settlers. Please continue reading to learn about retiring in Chestertown, MD.

Is Chestertown, Maryland a Good Place to Retire?

There are so many great reasons to consider retiring in Chestertown, MD. In a recent study done by SmartAsset, Chestertown was ranked second in the top 10 places in Maryland to retire to, right behind Easton. The distinction was based upon a variety of factors, including tax burden of income and sales tax, medical and the number of doctors' offices in the area, and recreation and social life, such as recreation centers and the percentage of seniors in the area. With its proximity to the Chester River and the Chesapeake Bay, outdoor activities such as boating, tubing, fishing, and swimming are quite popular among visitors and residents. The climate in Chestertown includes all four seasons with sub-tropical weather in the summer and cool temperatures in the winter. Chestertown is only an hour and a half drive from three major U.S. cities – Baltimore, Washington, D.C., and Philadelphia – allowing accessibility to big-city amenities and top-ranked hospitals, like Johns Hopkins Hospital.