Old Chappaqua Historic District

The Old Chappaqua Historic District is located along Quaker Road (New York State Route 120) in the town of New Castle, New York, United States, between the hamlets of Chappaqua and Millwood. It was the original center of Chappaqua, prior to the construction of the New York and Harlem Railroad and the erection of its station to the south in the mid-19th century. In 1974 it was recognized as a historic district and listed on the National Register of Historic Places.

What is today Chappaqua was first settled around 1740 by a group of Quakers from Long Island. They built the still-used Chappaqua Friends Meeting House, a Friends meeting house and the oldest known building in the town, around which the district centered a decade later. The other contributing properties, all timber frame buildings up and down the road on either side near the meeting house, are the surviving buildings from some of the farms established then and later. They have been preserved intact from that time.

The district begins on the west side of the road, approximately 0.6 mi (1 km) north of downtown Chappaqua and the Saw Mill River Parkway interchange, at 332 Quaker Road, just opposite Commodore Road. It follows the south line of that lot, then a line consistent with the west line of that lot through Fair Ridge Cemetery up to 478 Quaker, then turns 100 ft (30 m) to follow the north line and cross the road to take in 485 Quaker. It turns south at the lot corner to create a corridor 450 feet (140 m) wide with the road at the center south back to 385 Quaker, just north of Chappaqua Mountain Road, where it returns west to the road and continues back to its southern boundary.

The terrain is hilly, forcing the road through some gentle curves as it passes through the district. Despite the extensive residential development in the area, it is still heavily wooded, with many tall trees shading the houses and few clearings. Streams in the area drain into the Saw Mill River, which rises in the woods to the east. Quaker Road climbs approximate 140 feet (43 m) from south to north through the district.

Within this boundary, along a 0.6-mile (1 km) stretch of Quaker, are 33 acres (13 ha) with 30 buildings, half of which are contributing properties. All of them, whether contributing or not, are wood frame houses of two to three stories with gabled roofs. Those of more modern construction are sympathetic to their historic neighbors. Except for the meeting house, all are still used as residences. In the middle of a small grassy island at the Chappaqua Mountain Road intersection is a rock with a commemorative plaque to the district attached.

Quakers, fleeing religious persecution in England as Dissenters, settled in British colonies during the 17th century. One group established a meeting on Long Island in 1645. By the early 18th century their offshoots had crossed Long Island Sound to Westchester County, where they established Mamaroneck and Purchase by 1727.

In 1730, further offshoots of those groups moved further inland, to Wampus Pond (now Armonk) and "Shapequaw". Ten years later one of them, John Reynolds, established a 100-acre (40 ha) farm that included the area of the future district, along Quaker Road from Kipp Street to Roaring Brook Road. By 1747 there were enough Quakers in Shapequaw that they began petitioning the Purchase meeting to establish their own. Permission was granted shortly thereafter, and Reynolds donated two of his acres (8,100 m²) to the group so it could build a meeting house and burial ground.

By 1753 the meeting house was finished. In 1776 it would serve as a hospital for Continental Army soldiers injured at the nearby Battle of White Plains. Two years later a wing was built on it.