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

Bart Stolp
Main Street Historic Chestertown





Click above to view the Chestertown Road Trip feature article from Maryland Life Magazine.















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