Chestertown

The Chestertown downtown waterfront is a great place to walk, dine, and go back in history. There are many colonial homes, and the Riverwalk has park benches where you can sit and enjoy the view. The Sultana, an historic replica an American schooner that was captured by the British during the…Read more

Living working historic town on the Chester River. Tree lined brick sidewalks with unique shopping and dining.

Chestertown, the county seat of Kent, the Eastern Shore of Maryland's oldest county, was founded in 1706 and served as a major port of entry during colonial times. Its brick sidewalks and attractive antique stores, restaurants and inns beckon visitors and residents alike to wander, browse and…Read more

Chestertown is an historic small town on the majestic, unspoiled Chester River on Maryland's famous Eastern Shore. It has been since 1782 the home of Washington College. Many shops, restaurants, and bars are within walking distance, and a short drive through the surrounding farmland will take the…Read more

Chestertown is a 20 minute drive from Rock Hall. Great Farmers' Market on Saturday Morning!