Old Chappaqua Historic District

The Old Chappaqua Historic District is a corridor along scenic Quaker Road in the hamlet of Chappaqua that is home to twelve historic structures dating to the eighteenth and early nineteenth centuries. Included in the district are architecturally significant private residences, along with the 1753 Friends Meeting House, which served as the hub of the local Quaker community for generations, and Friends still continue to gather here. Early residents referred to this area as “Shapequaw,” and it is known today as “Chappaqua.” Homes, and the meeting house were constructed in the architectural styles typical of a rural agricultural settlement of the time period. When the railroad arrived in Chappaqua and New Castle in 1846, the tracks and depot were located to the east of the community where new development would occur, leaving the Old Chappaqua Historic District in many ways undisturbed. Although some of the structures have seen modifications over the years, they continue to exhibit many elements of their original design, providing a glimpse into life in this area two hundred years ago. The Old Chappaqua Historic District was placed on the National Register of Historic Places in 1974.

The area along Quaker Road (once named “Pines Bridge Road”) was originally settled by members of the Society of Friends around the year 1730. Early residents referred to the area as “Shapequaw,” and it is known today as “Chappaqua.” Quakers had moved across the mainland of New York (Westchester County) from Long Island where they had “established a Meeting” as far back as 1645. 

John Reynolds was a Long Island Quaker, who arrived to Chappaqua in 1740. He purchased land in today’s Kipp Street area, up Quaker Road, to Roaring Brook. From his large tract, he separated off two acres on Quaker Road, which he donated to the Society of Friends for the construction of a new Meeting House and burial ground. This is today the heart and center of the Old Chappaqua Historic District. Made with hand-hewn beams fastened with wooden pegs, the simple, sturdy meeting house was completed in 1753. In addition to religious services and instruction, the meeting house also played an important role in the American Revolution. After the Battle of White Plains, wounded soldiers were brought here for medical attention. In subsequent years, two additions were built on to the original structure in 1778 and in 1961.

Also included in the historic district are a number of private residences, many of which were constructed by members of the early Quaker community. These are: the ca.1740 Reynolds-Carpenter House; the 1765 Thorn-Dodge House; the eighteenth century Sutton-Reynolds House; the Thomas Dodge House of the late eighteenth century; the ca.1820 Stony Hollow Farm; and the Samuel Allen House from ca.1830

Although a number of the original buildings constructed in the Old Chappaqua Historic District have experienced additions or alterations, they continue to preserve crucial elements of their original design. They serve as enduring representations of a rural Quaker farming hamlet of Westchester County’s past. The Old Chappaqua Historic District was placed on the National Register of Historic Places in 1974.

1. Chappaqua Historical Society, Town of New Castle. Prepared by Dorothy Whitney Gruber in collaboration with Isabelle A. Haight. The Early Quaker Hamlet of Old Chappaqua: Its Houses, Its People, Its Way of Life. Chappaqua, NY. The Chappaqua Historical Society. 1973.
2. Chappaqua History Committee and Gray Williams. New Castle: Chappaqua and Millwood. “Images of America” series. Charleston, SC: Acadia Publishing, 2006.
3. “Old Chappaqua Historic District #74001319.” National Register of Historic Places. United States Department of the Interior/National Park Service. 1974. https://catalog.archives.gov/id/75323143 
4. Williams, Gray. Picturing Our Past: National Register Sites in Westchester County. Westchester County Historical Society. 2003.