The history of scenic Pleasantville is a rich patriotic fabric woven with the arrival of the first tenant farmers and laborers during Dutch Manor rule.

During the Revolutionary War, local militias were critical in the capture of British spy Maj. John Andre. The construction of the railroad in 1846 opened new markets for farmers and attracted many New York City professionals wanting an idyllic countryside family setting. It also initiated the tradition of the daily commuter. In 1908, the wealthy Manville family moved to the village, and the 1928 wedding of their daughter to the Count Folke Bernadotte of Sweden was a major international social event. That same year, Dewitt Wallace and his wife, Lila, moved to Pleasantville to launch Reader's Digest. Within 20 years, the Little Magazine would grow to 30 editions in 14 languages with a global circulation of 28 million every month. Throughout the years, the one thread that appears in this remarkable village from start to finish is a kind tradition of charity.