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Get to know Pleasantville

The name Pleasantville was bestowed by the village’s first postmaster and famously retained by Reader’s Digest after settling next door in Chappaqua. We’d like to think there was prescience for the easygoing place it would become—the kind of town where the fire department has their own band. To say it’s at peak pleasantness these days would be an understatement. You’ll find quaint, sidewalk neighborhoods, a vibrant downtown more akin to a Manhattan outpost than a suburban sanctuary, and the lush northern campus of Pace University. Jacob Burns Film Center, Pleasantville’s longstanding marquee attraction, screens foreign and independent films with frequent celebrity commentary, entertaining with engaging evenings of cinematic discussion. The woodlands above Kensico Reservoir host Frank Lloyd Wright’s Usonia, a mid-century modern enclave where 40-odd angular homes fade harmoniously into the rugged terrain. The more pastoral side of Pleasantville can be experienced at Rockefeller State Park Preserve, where generations of the family once enjoyed the same pleasant respite from the city you’ll experience today.

Nearby Neighborhoods:

Living in Westchester

Don’t call it upstate. This cosmopolitan county north of New York City is a collective of towns, hamlets and mid-sized cities that put virtually every lifestyle imaginable within an hour’s commute of Manhattan. It’s due north of the Bronx, next door to Connecticut, and the gateway to the Hudson Valley. Metro-North’s Harlem, Hudson and New Haven lines make for speedy service into Grand Central — an express ride from many down-county communities runs comparable to the F train from South Brooklyn, with a much sunnier view. Lower Westchester’s villages prioritize convenience, while the verdant horse country to the north is a favored destination for those looking to fade away in privacy. The Hudson and Long Island Sound form its two coasts, conspiring with an inland chain of lakes and reservoirs for unbeatable boating, fishing and other recreational endeavors. Chain stores are noticeably absent from many Main Streets, which run chockablock with character-filled indie shops.