Chestertown, MD

Eastern Shore life at its best

Chestertown, MD flourishes with a hearty blend of Colonial history, well preserved 18th and 19th century architecture, lively visual and performing arts and distinctive shops. Downtown bars and restaurants serve up warm hospitality and a range of dining options.

Chestertown is 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 admire. A visit to Chestertown’s Historic District is especially worthwhile, and includes a number of fine colonial residences, as well as some superb examples of later and more elaborate architectural styles.

Check out the rotating exhibits at RiverArts, Massoni Gallery and The Artists Gallery. Visit with furniture maker Bob Ortiz in his studio. Shop for fine artisan crafts at Create, and lose yourself in the shelves of a browser’s paradise called The Bookplate. Stroll down brick sidewalks to the Chester River waterfront to glimpse the schooner Sultana, admire the new Washington College boathouse, and experience the stunning Broad Reach sculpture at the entrance to Wilmer Park.

Come to Chestertown and enjoy Eastern Shore life at its best.

Find out more:
Visitors Center 410-778-9737

Eat. Drink. Buy Art in Chestertown, MD