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What does it mean to belong to a place? Standing in the famous gazebo at the intersection of multiple boundaries – the village of Chatham, the town of Chatham, and perhaps even the town of Ghent – this question feels especially important.

This rural upstate New York community actually comprises numerous Chathams: Old Chatham, North Chatham, East Chatham, Chatham Center, and the village itself. And, of course, Malden Bridge.

Through conversations with lifelong residents and relative newcomers, we get to know the layers of identity that define this rural community: Melissa Davis, who recently opened a boutique on Main Street with Sherri Marton (Marton & Davis), lovingly compares the village to Stars Hollow from Gilmore Girls, complete with quirky characters and a strong sense of community.

Meanwhile, Jeanne Veillette Bowerman, who manages an antique shop in the oldest building in the village (reportedly inhabited by 19th-century spirits), sees the ghosts of a Chatham that no longer exists.

The community stands at a crossroads of preservation and change. The historic Crandell Theater is being restored to its 1920s glory, though not to the version most longtime locals might remember. The Shaker Museum recently broke ground on a new headquarters. The Harlem Valley Rail Trail will soon connect Chatham to Wassaic, 46 miles away, and all the while, the Chatham Dirt Road Coalition fights to protect the town's 50-plus miles of unpaved roads from the pavers, seeing them as essential to maintaining rural character here.

Hidden histories emerge at every turn – from the modest farmhouse where the Three Stooges once lived to avoid the World War I draft to the 153-year-old clock still keeping time above Main Street. Each story reveals how communities navigate the delicate balance between honoring the past and embracing the future.

To hear my previous episode in Chatham, featuring our anonymous food critic The Hungry Eye and the Great Chatham Bake-Off, click here.

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"The Jiffy Audio Newsletter Podcast" is an audio documentary zine – the official podcast of The Jiffy – exploring the odd histories, cozy mysteries, and surprising characters of upstate New York. Each episode is a small adventure, told with curiosity, humor, and the occasional text message from a stranger.

New episodes drop every other week. Subscribe, share, and take the scenic route with us.

Follow James on Instagram: @jamescave

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