Pleasantville is a village in the town of Mount Pleasant, in Westchester County. Pleasantville is home to a campus of Pace University and to the Jacob Burns Film Center. It was the original home of Reader’s Digest, which still uses a Pleasantville postal address. Most of Pleasantville is served by the Pleasantville Union Free School District, with small parts of northern Pleasantville served by the Chappaqua Central School District. The village is also home to the Bedford Road School, Pleasantville Middle School, and Pleasantville High School.
The settlement of Pleasantville dates back to an Iroquois tribe, who raised corn there and established trading routes crossing through the present-day village before the arrival of Europeans 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, where there were conflicting loyalties among the settlers. British spy Major John Andre’ passed through present-Pleasantville carrying information from Benedict Arnold at Fort Clinton to the British in New York City. André lost his bearings near the present-day corner of Bedford Road and Choate Lane and was captured in Tarrytown. The capture of André is often cited as a key factor in the ultimate victory of the American forces.
As the area’s population grew in the early 19th century, the settlement was 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 the name. His second choice, Pleasantville, was accepted, and the Pleasantville Post Office opened on February 29, 1828.
A significant change in the development of Pleasantville came with the arrival of the New York Central Railroad and New York and Harlem Railroad in 1846. 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 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 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. According to several sources, 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 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 at about 1886. 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.