Early Life

The marriage of Jacob’s parents, Thomas Wynkoop and Jane Deyo, is listed in the records of the Reformed Church of New Paltz as taking place in January 1827, barely six months before slavery officially ended in New York State on July 4, 1827. Jacob’s father Thomas had been enslaved by Dirck D. Wynkoop. Wynkoop, on his own and later with his son-in-law Peter Eltinge, operated a substantial wheat plantation on “the Plains” south of the village of New Paltz. In 1798, Wynkoop and Eltinge jointly owned thirteen enslaved adults, more than any other slaveholder in New Paltz.  A stone outbuilding on the Wynkoop-Eltinge property has long been thought to have served as the living and sleeping quarters for those enslaved people. This contrasts with smaller farms, more typical of New Paltz and most of Ulster County, where it was common for the enslaved to sleep in cellars or attics of their enslaver’s homes. Jacob’s mother Jane had been enslaved by Jonathan Deyo, who had a farm on the west side of the Wallkill River on the road to Libertyville. Like many of those enslaved, after manumission Jacob’s parents assumed the surnames of their slaveholders.[1]

Thomas Wynkoop and his wife Jane appear in the 1830 federal census, living in New Paltz and listed as “free colored persons.” Their two sons, John (born in 1827) and Jacob, are recorded as well. The family lived on what is now Water Street, probably in a house for workers at the nearby mill. Jane’s mother Isabella and her husband Philip DuBois lived nearby (the older couple had been married at the Dutch Reformed Church in 1826).[2]

Ulster County land records show that Jane Deyo Wynkoop, Jacob’s mother, bought one quarter acre from Maria Hasbrouck for $25 in 1840 (about $742 in today’s currency). The property was located on the crest of a hill on the eastern edge of the original village lot of New Paltz patentee Abraham Hasbrouck (now Church Street). This is one of the earliest, if not the earliest, documented purchases of land by an African American–man or woman–in New Paltz. Undoubtedly, the purchase was a testament to Jane’s hard work and careful planning, as well as some respect in the white community. Few other African Americans at the time were as fortunate. Once the state made the practice of slavery illegal, many freed Blacks left the area in pursuit of jobs and a better way of life. Those who remained often worked as servants in the houses of white families or ended up in the Ulster County Poorhouse. To learn more about Jane and this exceptional purchase, please visit the online exhibit Jane Deyo Wynkoop.[4]