Deep in the historic background of Scarsdale is a romantic twist of fate. In 1666 during Charles the Second's reign, a sixth son Caleb was born in the family of Mayor Heathcote of Chesterfield in the Hundred of Scarsdale, Derbyshire, England. Some twenty-six years later, after his intended wife had transferred her affections to one of his older brothers, a disappointed Caleb Heathcote took his patrimony and set sail for New York. Prospering in trade, he soon became one of the leading men of the colony and began to buy up land in Westchester. At the end of the century he purchased from Ann Richbell the claims her husband had established to land running nine miles back from Long Island Sound to the Bronx River and averaging two miles in width. Shortly thereafter he purchased the Fox Meadow from the Indian chiefs, among whom was Cohawney, and then acquired a bit more land to the south along the Bronx River, rounding out his holdings to the town line in Eastchester.

In 1701 Caleb, who had become influential in the government of the province, had these lands elevated into a royal manor. He named the area Scarsdale after his ancestral home. Since the English name meant "dale of scars or rocks," it was appropriate here as it was there. Scarsdale was one of nine royal manors of New York, six of which were in Westchester County. The first population count taken in 1712 listed 12 people, seven of whom were slaves. After Caleb's death in 1721, the land was inherited by his two daughters. In 1774 the manor was broken up, and the tenants became the proprietors. Scarsdale became a town by the law of March 7, 1788.

During the American Revolution, both the Continental and British armies passed through parts of Scarsdale. After a brief battle near the junction of modern Mamaroneck and Garden Roads, General Sir William Howe spent some time in the Griffen farmhouse. The house still stands, identified by a bronze marker. Tradition has it that the Varian house, now known as Wayside, was the scene of a fracas when Tory marauders tried to find the family cow which had been locked in the house. A generation later James Fenimore Cooper, who had married a great grand-daughter of Caleb Heathcote and at that time lived on the Angevine Farm on Mamaroneck Road, gave the story of those turbulent days a permanent place in literature. Deeply impressed with reminiscent tales he had heard from the aged John Jay, Cooper, while living in Scarsdale, wrote The Spy, which became the first American novel.

At the time of the first federal census in 1790, Scarsdale's six and one-half square miles held 281 inhabitants. Fifty years later that figure had declined slightly so that in 1840 Scarsdale had 255 residents, and all but four of its adult men worked as farmers or farm workers. Lacking access to navigable waterways, Scarsdale fell behind the towns that bordered Long Island Sound and the Hudson River.

The town's fortunes improved, however, after 1846 when the New York and Harlem Railroad (later a division of the New York Central) began service in the Bronx River Valley. As New York City grew and became more crowded, more and more residents of the city who could afford the cost of commuting began to consider living elsewhere. During this period of the 1850s Scarsdale included a post office, a livery, a school, and two churches, in addition to the all-important stop on the railroad. Although several houses were located near the train station, there were no stores, no street lamps, and no paved streets. To the east and north of the station stood the community's farms along with the estates of a few wealthy residents who had moved into the suburbs.

It was the Arthur Suburban Home Company that initiated the change from a rural town to a residential suburb. In 1891 it purchased a 150-acre farm and turned it into a row of one-family houses. Covenants included in every sale prevented the use of any lot for commerce.

By 1900, the population stood at 885, and Scarsdale, as we know it, began to appear. In 1904, the Heathcote Association, the first Neighborhood Association, and the Town Club, the predecessor of the Town and Village Civic Club, were formed. The Scarsdale Woman's Club was organized in 1918 and one year later began publishing The Scarsdale Inquirer. For the next forty years this prize winning paper was owned, managed and staffed by women. In 1921 the Scarsdale League of Women Voters was formed and began meeting as part of the Public Affairs committee of the Scarsdale Woman's Club. The Town's first store opened in 1912 at the corner of Popham and Garth Roads. Scarsdale High School and Greenacres Elementary School were built in 1917, Edgewood in 1918. In order to prevent Greenacres from being annexed by White Plains, Scarsdale was incorporated as a Village in 1915. (A village may only be annexed by a vote of its citizens; the boundaries of a Town may be changed by the State Legislature.) The population then was almost 3,000.

The Twenties saw a building boom that tripled the population by the end of the decade to 9,690. The Bronx River Parkway, the first parkway in the country, was opened in 1924. New stores and banks opened on East Parkway and Popham Roads. Fox Meadow and Crane-Berkley were developed. Heathcote's "Five Corners" thrived, although the New York, Westchester and Boston Railroad, around which it had been built, did not survive. Fox Meadow Elementary School was built in 1928. Many of the Tudor-style houses and business fronts date from this period. In 1922 the Village Board adopted a Village-wide zoning plan, the first zoning law passed in New York State by a suburban community. Court challenges to the code have been met successfully, and Scarsdale has remained primarily a residential community of single-family detached houses.

Another building boom occurred after World War II. The area that experienced the greatest development was Quaker Ridge, which derived its name from its early Quaker settlers. Quaker Ridge Elementary School opened in 1947, Heathcote in 1953 and the Junior High School (now the Middle School) in 1956. The Village and School Districts purchased land for both public use and open space. Major strides in community recreation included public tennis and paddle courts, public day camps, a swimming pool complex and a vast array of programs. Now the Village appears to have entered a new era of relative population stability as a result of the almost complete development of its privately owned land. Scardale's 1990 population was approximately 17,000.

Scarsdale residents have enjoyed success in many fields. James Fenimore Cooper, mentioned earlier, wrote The Spy. Daniel D. Tompkins, five times Governor of New York(1807-1815) and twice Vice President of the United States, was born here. Other Scarsdale residents include distinguished scholars and artists, university presidents, a Nobel prize winner, state senators, members of Presidential cabinets, an astronaut, a New York State Commissioner of Education and presidents of large corporations. Many residents have given and continue to give their time and talents to serve Scarsdale by accepting positions as Mayor, Village and School Board members and as leaders of over 80 organizations.