33 Kipp Street Chappaqua, NY 10514

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.