The settlement of Pleasantville dates back to the Rechgawawank and Sinsink tribes, belonging to the Munsee dialect of the Lenni Lenape.

[3] Lenape communities practiced ecosystem management, small-scale agriculture, hunting and gathering, democratic politics, and matrilineal governance.

[4] French Huguenot Isaac See[nb 1] settled here as an agent for Dutch landowner Frederick Philipse in 1695, beginning the modern settler-colonial history of Pleasantville.

André lost his bearings near the present-day corner of Bedford Road and Choate Lane and was captured in Tarrytown, New York.

In 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 railroad offered a speedier and more frequent connection with New York City—only 70 minutes away by rail, compared with a five-hour overland journey by stagecoach or a two-hour steamboat trip down the Hudson River.

The present-day train station, which currently houses a restaurant, was built in 1905 and was moved to its present location in the 1950s to accommodate the lowering of the tracks below grade.

Before the addition of the now heavily trafficked station, commuters working in New York City and lower Westchester County were forced to rely on rides from Marc Damon, now famous in Pleasantville for being "The Friendly Coachman".

[8][12][13][14] According to several sources,[15] 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 the north.

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.

[17][18] In the following years, Pleasantville quickly developed into a 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.

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.

Today Pleasantville is home to many novelists, editors, and writers, who find its easygoing charm and proximity to New York an attractive combination.

Guest speakers at the Burns Center have included Jerry Lewis, Woody Allen, Jonathan Demme, Robert Klein, Oliver Stone, Stephen King, Rob Lowe and numerous other notable filmmakers and actors.

Main stage acts have included Roger McGuinn, The Bacon Brothers, Rusted Root, Jakob Dylan, Dar Williams, Carney, Back Door Slam, Marc Cohn, Augustana, Z.Z Ward, and Joan Osborne.