9 Grandview Drive Pleasantville, NY 10570

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.