The Chappaqua Summer Scholarship Program (CSSP) was founded in 1968 when two longtime Chappaqua friends despaired over the educational crisis in New York City.
Our Founding Story
The Mahicanni (Mahicans) dominated the area on the east bank of the Mahicanituck (Hudson River) in 1609 when Henry Hudson arrived. The Wappinger Confederacy was part of the Mahican nation and occupied Westchester and Putnam counties, the Bronx and Manhattan, the majority of Dutchess county and parts of Connecticut.
Nathaniel Turner purchased parts of New Castle in 1640 from Ponas Sagamore, ruling chief of the Siwanoy. In 1661 John Richbell purchased a large tract of land including New Castle from Wappaquewam, who is rumored to be a Siwanoy, and in 1696 Caleb Heathcote purchased the same land again from Richbell’s widow and the Sachems Wabetuck and Cohawney who were supposedly Siwanoys.
In New Castle the Sint Sinks, located in the western part of the town, and the Tankiteke, in the eastern part, were abundant especially between the middle and towards the end of the 18th century. By the late 18th century their numbers had dwindled, and they were completely gone from the area by 1791. Indian villages or sites include Chappaqua hill (between Quaker St and the railroad), the Sutton Reynolds farm, Wolf Hill Road, Roaring Brook, New Castle Corners, the Old VanTassel farm, “Coyemong” at Byram Lake, Wampus Lake, and near the Ossining border.
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.
On April 5, 1791, New Castle held its first town meeting. Until then, it had been part of the Town of North Castle. Residents from colonial times until the middle of the 19th century were largely self-sufficient farmers, part-time millers and craftsmen.
When the railroad came to Chappaqua in 1846 and to Millwood in 1881, the farms began to grow and ship “cash crops.” To package and ship the cider, vinegar, apples, milk and other products, residents built cider mills, a pickle factory and a barrel factory. The two hamlets of Chappaqua and Millwood developed freight stations, livery stables, general stores and hotels. Later 19th century industries included the Spencer Optical Works, near Mount Kisco, and the Bischoff Shoe Company in Chappaqua. Nevertheless, the Town remained a very small town, with 1,800 people in 1850 and less than 2,500 at the end of the century.
Gradually, the local industries lost their vitality, but the beauty of the land and the relative ease of transportation provided by the railroad remained and began to attract people who had accumulated wealth in New York City. Among these was Horace Greeley, who first bought land in Chappaqua in 1853, later owned the current “Horace Greeley House” and a large part of central Chappaqua, including the grounds of the Robert E. Bell Middle School. Greeley was America’s foremost newspaper editor, and an unsuccessful Presidential candidate, losing to Grant in 1872. The wealthiest of the residents was probably banker Moses Taylor, whose estate included the land where the Mt. Kisco Country Club currently stands.
In 1902 the current Chappaqua railroad station was built—the original station was further north on North Greeley Avenue. Millwood’s first station was built in 1888 at a cost of $1,800. It burned soon after. For several years, the station was a baggage car. The present station was brought by flat car from Briarcliff Manor when Henry Law built and gave the Briarcliff station to the railroad in 1910.
In 1904 the town’s worst disaster, a tornado, swept down Quaker Street, stopping just short of the Quaker Meeting House. In 1912, Chappaqua put in its first central water system.
Following the World Wars, the population of the town grew greatly. In the 1920s, realtors promoted “the high pure air belt of Chappaqua.” The Saw Mill River Parkway reached the Town in 1934 and in the late 30s and 40s lasting real estate developments took root. The most dramatic population increase came in the years following World War II. From 1950 to 1960 the number of people in New Castle rose by 60% to more than 14,000. A major factor in this increase was the acknowledged excellence of the Chappaqua school system.
New Castle has been fortunate to retain much of its early charm—partly because of its vigorous terrain, and partly through the care given by owners, residents, and town government to its historic buildings and areas.