Chesapeake Charm

An independent spirit and loads of local color make Chestertown, Maryland, one of our all-time-favorite small towns.

I've been exploring Chestertown’s redbrick sidewalks for only an hour, but I’m already mesmerized by its picture-perfect scenes. Streams of yellow sunlight filter through the leafy green canopy, beaming on a tidy row of shops with inviting windows.

I spent last night at The Imperial Hotel--recommended by a friend as a fine retreat--and arose this morning to wander toward the river. There, a tiny flotilla of sailboats gently bobs in the calm water as birds fly overhead. The Sultana, a replica of a historic schooner, sits tied to the dock. In its quiet berth, it looks ready for adventure.

I follow a narrow walk between 18th-century homes. Peeking into the lush gardens, I breathe deeply the heady scents. Dark red roses cascade over the old white picket fences, and sidewalks are littered with soft petals just like a wedding aisle. Over in Fountain Park, the town square, people gather for the Saturday morning farmers market.

An Independent-Minded Place
Beneath the quiet historic exterior, energy buzzes throughout this village that hugs the Chester River. Proud of all the locally owned businesses, they strive to keep Chestertown’s small-town charm. For instance, they refused Wal-Mart moving in, and another time they opposed a proposed bridge across the Bay, hoping to keep out the mainland’s congestion. Consequently, they’ve preserved their village’s authenticity.

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