Chestertown, Maryland is a small town on the Eastern Shore, in Kent County, one of Maryland’s least populous counties. It sits on the Chester River, which winds inland from the Chesapeake Bay starting just north of Kent Island, and separates Kent and Queen Anne counties. (Kent Island is actually part of Queen Anne County.) Like most Eastern Shore rivers, the Chester is really just an extension of the Bay, placid and tidal.
Chestertown is reached by heading north on Rte. 301 at the 301-50 split in Queenstown. This distinguishes it from the rapidly developing communities along Rte 50, like Kent Island, Easton, and Cambridge, and from the mass of traffic that heads through these places to Ocean City, MD every summer weekend.
Kent County has a few other towns, most notably Rock Hall on the Bay, but is mostly rural. The county comprehensive plan is intended to maintain that, and emphasizes new development around existing population centers. This is in contrast to Queen Anne County, where developments appear to be springing up in cornfields everywhere.
Chestertown was once a major port of call on the Chesapeake. It has a large number of well-preserved or restored old homes and other buildings, along and close to the waterfront, and a downtown area with a number of eclectic shops and small restaurants.