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 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.

Second largest district of restored 18th-Century homes in Maryland, Chestertown is also home to Washington College, the nation’s tenth oldest liberal arts college, founded in 1782.

Things to do in and around Chestertown

Golf – Chester River Yacht & Country Club

Horse Riding – Kent Equestrian Center

Wine – Crow Vineyard

Fishing and Boating

Cheasapeak Bay Fishing – Rock Hall Fishing Charters

Kayak and Canoe Rentals – Chester River Outfitters

Tall Ship – Sultana

River Cruise – Chester River Packet

Hunting and Sporting Clays

Sporting Clays – Hopkins Game Farm

Guided Hunting – Eastern Shore Guide Service