The settlement of Pleasantville dates back to the Rechgawawank and Sinsink tribes, belonging to the Munsee dialect of the Lenni Lenape. This region of the Hudson Valley has been inhabited since just after the last ice age. Lenape communities practiced ecosystem management, small-scale agriculture, hunting and gathering, democratic politics, and matrilineal governance. Called the “Grandfathers” by neighboring tribes, the Lenape were peaceful and skilled at conflict resolution between tribes and established trading routes crossing through the present-day village before the arrival of Europeans. By the end of the 17th century, most if not all of the New York Lenape people had been killed by disease or conflict or had been displaced westward; Lenape in the 21st century reside in Ontario, Oklahoma, Ohio, Wisconsin, New Jersey, and Pennsylvania. French Huguenot Isaac See settled here as an agent for Dutch landowner Frederick Philipse in 1695, beginning the modern settler-colonial history of Pleasantville.