Brought to Woodstock as a “rickety babe” after being purchased by Isaac Fellows for a pistereen, Cuff Fellows lived and worked in the household of Leah Paine Fellows and her husband, Isaac, until his manumission in 1798. In 1792, while still enslaved, Cuff married a woman named Dinah, who had been enslaved in a Malbone household in nearby Brooklyn. The marriage took place in Old Trinity Church, a building that was reportedly constructed by the enslaved persons owned by the Malbone family. Cuff and Dinah had several children, all of whom were baptized in the First Church of Woodstock, along with their mother, in 1810.