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Rooted in history, and adapted to contemporary life, historic Chestertown captures small town living in a way that will capture your heart. Stroll our tree-lined brick sidewalks and discover unique shopping, historic homes and buildings, and fine regional cuisine. Mingle with locals and visitors alike enjoying the evening atmosphere of First Fridays with opening receptions and demonstrations by artists in shops and galleries all over town.

The Chestertown Farmers’ and Artisans’ Market serves a feast for the senses each Saturday morning in Fountain Park with a bounty of fresh fruits, produce, flowers, meats, cheeses, wines and handmade crafts.

Opportunities to enjoy nature abound, with miles of back roads, trails, creeks and of course the beautiful Chester River to explore by foot, bicycle, kayak or boat.

Chestertown is located a swift 60 minute drive from Annapolis and less than two hours from Philadelphia, Wilmington, Baltimore and Washington, DC.

Once in the heart of Downtown, you’ll find plenty of free parking, both on street and in public lots. A variety of lodging options await you to provide perfect jumping-off points for exploring. Visit www.townofchestertown.com or www.kentcounty.com for additional visitor information and sample itineraries.