Chappaqua

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Get to know Chappaqua

We’re confident Horace Greeley, the prolific publisher who long lived here, would agree Chappaqua is a place to write home about. The household-name hamlet of the less-familiar town of New Castle, this Northern Westchester village is often compared to its Lower Westchester counterparts for its overall layout and feel. Its name, a Quaker remix on the Algonquian word “shah-pah-ka,” loosely translates to “the rustling land,” and the gentle brushing of windswept leaves still hums the ambient soundtrack in this wooded valley today. Since the Harlem Line rolled through in 1846, commuter trains have ushered city types and locals alike to enjoy its plentiful suburban spoils. Boutiques and edible-specialty shops tag-team with galleries and green space downtown, which stems off in all directions towards wooded neighborhoods of antique Colonials, crosshatch-windowed stone manors and the occasional mid-mod. Head to the old, stone train station for a trip into Manhattan, a minimal 38 miles away, or to simply enjoy farm-to-table fare at the depot café.

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Chappaqua 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.