The Old Chappaqua Historic District was listed on the National Register of Historic Places in 1974. Portions of the content on this web page were adapted from a copy of the original nomination document. 
Situated on wooded, hilly terrain, the Old Chappaqua Historic District is composed of a corridor, 450 feet wide, along Quaker Road. Contained within these bounds and clustered around the wood-frame Meeting House are twelve structures of the late 18th-early 19th century hamlet of Old Chappaqua — all simple examples of a vernacular architecture typical of agricultural settlements of the period.
Standing on a slight rise on the west side of Quaker Road, the original, two-story, gable-roofed structure, sheathed in clapboards, measures five bays in length and two bays in width. A one-story veranda extends the length of the south and east elevations. Within, chamfered wood posts support a gallery on the east, west, and north sides of the structure. The Meeting House has been enlarged twice: first in 1778-1780 by the addition of a 20-foot by 18-foot wood-frame wing in the west side, and second in 1961 by the construction of a west wing designed by Livingstone Elder.
Reynolds-Carpenter Farmhouse and the Sutton-Reynolds House
These two wood-frame farmhouses were erected on part of John Reynolds' 100 acres, presumably for two of his seven sons. The two-story, gable-roofed, five-bay wood-frame structure is the original portion of the Reynolds-Carpenter House. The rear wing, also constructed of wood-frame sheathed by clapboards and measuring two bays by two bays, was added in 1850 by Robert Carpenter. Immediately north of the house stands a 19th century wood-frame barn.
The Sutton-Reynolds House, situated north of the Reynolds-Carpenter House, is a two-story, gable-roofed wood-frame dwelling measuring five bays in length. Two interior end chimneys served the structure, erected according to a central hall plan.
Samuel Allen Farm
Part of a tract farmed in the 18th century by the Underhill Family, the Samuel Allen Farm today is evidenced by the main house (c.1830), the tenant house (c.1850), the currying shop (c.1820), and an old barn (c.1833). All are wood-frame construction, four bays in length, and varying from one and a half to two stories high. Like the Thomas Dodge House, the currying shop (later harness shop) was built against a rise thereby leaving the cellar walls exposed on the front elevation. Worthy of note is the exposed brick fireplace-back on the west wall of the tenant house.
Stony Hollow Farmhouse
Originally part of the Brady Farm, the farmhouse (c.1820) and barn are both wood-frame structures, the former sheathed by clapboards, the latter by shingles. It is believed that the present two story house may be the product of enlargement at various points during the 19th century.
Thorn Dodge House
The original structure is that portion of the dwelling which now functions as the rear wing. Built by Elnathan Thorn close to the road, the small, wood-frame dwelling was moved to its present position in 1852 when Henry Dodge, cabinetmaker, built the five bay by two bay house visible from Quaker Road. Composed of a wood frame sheathed by clapboards, the structure stands two stories high, covered by a gable roof. The dependencies on this property were demolished by a tornado in 1904.
Measuring three bays long and two bays wide, the wood-frame dwelling was constructed against a hill so that it stands two stories high on the east (front) side and one and a half stories on the west. The original occupants were cabinetmakers Thomas Dodge (1778-1856) and Hannah Reynolds Dodge.
Of special interest when viewed in the context of the extensive suburbanization of Westchester County, the Old Chappaqua Historic District comprise the heart of the rural hamlet of "Shapequaw" settled by the Quakers in the middle of the 18th century. Focused around the wood frame Meeting House where Friends still gather regularly, a substantial number of early farm structures have survived within a still wooded tract of land and comprise a still recognizable entity despite modern residential growth in the vicinity.
From Long Island where they had established a meeting in 1645, Quakers crossed to the mainland of New York (Westchester County), settling in Mamaroneck and Purchase (1727). Around 1730, Quakers moved northward and began to settle in the area known as "Shapequaw" (Chappaqua) and at Wampus Pond (now part of Armonk).[‡] According to the records of the Purchase Monthly Meeting (August, 1747), the Friends then residing in "Shapequaw" had for some time met together in the home of Abel Weeks, and at that time sought permission to establish an official meeting in the area.
In 1740 John Reynolds had moved from Long Island to "Shapequaw" where he acquired a farm of 100 acres, stretching from present Kipp Street up Quaker Road to Roaring Brook Road. When permission to establish a Meeting was granted to the settlers of "Shapequaw," John Reynolds gave the community two acres for a meetinghouse and burial ground. In 1753 the residents constructed the wood-frame Meetinghouse to which wounded soldiers were brought after the Battle of White Plains during the Revolution.
Throughout the 18th and 19th centuries Chappaqua was essentially a farming community, a hamlet scattered along what is now Quaker Road from the area north of the Meetinghouse south, and out along Kipp Street. The present Old Chappaqua Historic District comprises the heart of the old hamlet which, despite the intensive suburbanization of much of Westchester County, has survived, primarily because the Harlem Railroad in 1846 was built east of the settlement. The depot took over the role of the meetinghouse as the magnet for development. As a result, the historic center of the community, composed of simple agricultural structures clustered around the substantial wood-frame Meetinghouse where the Society of Friends still holds weekly meetings, is still clearly discernible.
The Old Chappaqua Historic District consists of a cluster of late 18th-early 19th century vernacular structures within a wooded hilly context. The simple, rectangular, wood-frame buildings, ranging from 1-1/2 to 2-1/2 stories in height, for the most part, illustrate the building form typical of rural domestic architecture of the period throughout Westchester County. Two dependencies on the former Samuel Allen Farm, also executed in wood, provide examples of the same building traditions utilized for other functions common to agrarian settlements of the period. The wood frame Meeting House, which forms the nucleus of the Old Chappaqua Historic District, is one of a small number of Friends Meeting Houses remaining in southern New York similar in style and distinctive for their remarkable degree of architectural integrity, both inside and out.
[‡]The Wampus Pond Meetinghouse now functions as a barn. The last remaining dwellings were demolished when the New York City Waterworks Commission acquired jurisdiction over Wampus Pond.
Gruber, Dorothy Whitney and Isabelle Haight. An Illustrated History of the Early Quaker Hamlet of Old Chappaqua. New Castle: Chappaqua Historical Society, 1972.
Gruber, Dorothy Whitney and Isabelle Haight. The Early Quaker Hamlet of Old Chappaqua...Its Houses...Its People...Its Way of Life. New Castle: Chappaqua Historical Society, 1972. Based on documents on file in the Westchester County Surrogate's Office, and the Land Records Office, White Plains, NY.