There were 2,637 households out of which 35.2% had children under the age of 18 living with them, 58.3% were married couples living together, 7.8% had a female householder with no husband present, and 30.8% were non-families. 25.6% of all households were made up of individuals and 10.3% had someone living alone who was 65 years of age or older. The average household size was 2.61 and the average family size was 3.16.
In the village the population was spread out with 28.5% under the age of 18, 4.8% from 18 to 24, 29.9% from 25 to 44, 23.5% from 45 to 64, and 13.3% who were 65 years of age or older. The median age was 38 years. For every 100 females there were 98.3 males. For every 100 females age 18 and over, there were 91.1 males.
The median income for a household in the village was $86,632, and the median income for a family was $105,227. Males had a median income of $62,344 versus $47,978 for females. The per capita income for the village was $41,397. About 2.0% of families and 4.4% of the population were below the poverty line, including 3.0% of those under age 18 and 3.5% of those age 65 or over.
Pleasantville has a long and rich history going back to the days of the original inhabitants, members of the Algonkian tribe (sometimes identified as the Tankitekas), who raised corn here and whose trading routes crossed through the present-day village long before the arrival of the Europeans. French Huguenot Isaac See (sometimes spelled Sie) settled here as an agent for Dutch landowner Frederick Philipse in 1695, thus beginning the modern history of Pleasantville.
By the time of the American Revolution, the population of the growing settlement comprised English, Dutch, and Quakers, most of whom were tenant farmers. During the Revolution, this area was part of the Neutral Ground; conflicting loyalties during this period set neighbor against neighbor and even split families apart. The infamous British spy, Major John Andre, passed through what is now Pleasantville on a mission to carry information from Benedict Arnold at West Point to the British in New York City. Andre lost his bearings near the present-day corner of Bedford Road and Choate Lane. As a result, Andre fell into the hands of the American Army. The capture of Andre is often cited as a key factor in the ultimate victory of the American forces.
As the population grew in the early 19th century, the settlement was often called Clark’s Corners, referring to property owned by Henry Clark at the intersection of Broadway and Bedford Road. This area was the village’s original commercial center. In the 1820s, the newly appointed postmaster, Henry Romer, was directed by the Postmaster General's office in Washington, D.C., to give a name to the post office planned here. Romer's proposed name, Clarksville, was rejected because another New York post office already had that name. His second choice, Pleasantville, was accepted and became official when the Pleasantville Post Office opened on February 29, 1828.
Perhaps the greatest change in the history of Pleasantville came with the arrival of the New York Central Railroad and Harlem Railroad in 1846. The following year a train station was built near the present corner of Bedford Road and Wheeler Avenue, and as a result the commercial center of Pleasantville shifted to its current location. The older business district at Bedford Road and Broadway is today called the Old Village. The railroad offered a speedier and more frequent connection with New York City—only 70 minutes away by rail, compared with an arduous five-hour overland journey by stagecoach or a two-hour steamboat trip down the Hudson River. The present-day train station, which currently houses the Iron Horse Grill restaurant, was built in 1905 and was moved to its present location in the 1950s to accommodate the lowering of the tracks below grade.
According to several sources, including the village’s website, Pleasantville was a stop on the Underground Railroad, a network of safe houses for escaped slaves from the South on their way to freedom in Canada.
The latter half of the 19th century was a time of rapid growth in Pleasantville. By the 1870s, there were four shoemaking businesses, a shirtmaking business, and a pickle factory. The first newspaper to serve the village, ‘’The Pleasantville Pioneer,’’ was launched in about 1886. And the village’s numerous small farms and orchards began to be subdivided for a wave of solid foursquare and Victorian houses built for a growing middle class. The 1890s saw the establishment of a police department, volunteer fire department, and a library system. Pleasantville was incorporated as a village on March 16, 1897.
In the years since then, Pleasantville quickly developed from a country village into a bustling modern suburb of New York, with a large number of workers commuting between the village and the metropolis on what is now the Metro-North Railroad’s Harlem line. During the first two decades of the 20th century, roads were paved for the first time, water mains were installed, and electrical wires brought power to the village’s houses. Other improvements during the first half of the 20th century include Soldiers and Sailors Field in 1909, the Saw Mill River Parkway in 1924, the Rome Theater in 1925, Memorial Plaza in 1930, Parkway Field in 1930, and Nannahagen Park in 1937 (the adjacent village pool was completed two years later). By the time of World War II, the village had taken on the appearance that it bears today.
Pleasantville merits interest for its literary history. Playwright Lillian Hellman (‘’The Children’s Hour,’’ ‘’The Little Foxes’’) bought Hardscrabble Farm on the western outskirts of Pleasantville and lived there in the 1940s and 1950s. For many years author Dashiell Hammett (‘’The Thin Man,’’ ‘’The Maltese Falcon’’), with whom Hellman was romantically involved, lived and worked at Hardscrabble Farm. Dewitt Wallace and Lila Bell Wallace, co-founders of Reader's Digest, made Pleasantville their headquarters in 1922, using a converted garage and pony shed on Eastview Avenue as their office and later building a home and larger office space on adjacent property. Subsequently the Digest held office space in several buildings throughout Pleasantville, including the present-day Village Hall at Bedford Road and Wheeler Avenue and, diagonally opposite, the bank building currently occupied by Chase. Reader’s Digest moved its headquarters to nearby Chappaqua in 1939, but retained its Pleasantville post office box, thus making the name of the village familiar to millions of Reader’s Digest subscribers around the world. Today Pleasantville is home to many novelists, editors, and writers, who find its easygoing charm and proximity to New York an attractive combination.
Pleasantville’s reputation as a cultural center was enhanced in 2001 with the opening of the nonprofit Jacob Burns Film Center in the landmark Rome Theater, a Spanish mission-style building and one of the first movie theaters in Westchester County. The Burns Center is dedicated to presenting independent, documentary, and world cinema. Guest speakers at the Burns Center have included Jerry Lewis, Woody Allen, Jonathan Demme, Robert Klein, Oliver Stone, Stephen King, and numerous other notable filmmakers and actors.
In 1948, in an unincorporated area of Pleasantville off Bear Ridge Road, acolytes of Frank Lloyd Wright began putting their lessons to work by building homes in their mentor’s modernist, open-plan style. The neighborhood, called Usonia, comprises 50 houses spread among 100 acres of wooded hillside; the development includes two houses designed by Wright himself. Students of residential architecture and fans of Wright’s designs will find the area of interest.
Another addition to Pleasantville’s cultural scene is the Pleasantville Music Festival, an all-day outdoor event in July. In previous years main stage acts have included Roger McGuinn, Dar Williams, and Jonathan Edwards.