A center of commerce since the early 1700s, Chestertown is an Eastern Shore town where you can enjoy a relaxing weekend of boating, biking and seafood, amid delightful surroundings.

Chestertown, situated on the banks of the Chester River, has a dozen or more art galleries that feature both local and more widely-know artists. The town also has numerous well-preserved 18th- and 19th-century homes that formerly belonged to wealthy Chestertown merchants.

As you stroll along the waterfront promenade, you might see the Schooner Sultana – a replica of an 18th century schooner that takes students on educational trips around the Chesapeake Bay.

A visit to downtown Chestertown offers a blend of history, arts, shopping, and an exciting variety of lodging and dining experiences.



Contact Chestertown Main Street

Kay MacIntosh
Main Street Historic Chestertown
(410) 778-2991