John Wynkoop with a white horse, ca. 1888. Photographic print from glass plate negative. HHS Archives, gift of Amy LeFevre.
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John was born June 27, 1827, just one week prior to the manumission of slaves on July 4th of that year. According to NYS law, John (having been born before his mother was emancipated) could have been bound to service of a master for twenty-one years. It’s unclear if this happened to John. 
John worked as a laborer all his life, sometimes on farms but often on construction projects with his brother Jacob or other builders. He and Jacob are known to have worked on portions of the Mohonk Mountain House. The 1855 New York State census listed John as married, but his wife was not residing with him. If the census information is correct, she might have been working as a live-in servant at that time, as Jacob’s wife had done early on. Without a name, it may be impossible to know who John’s wife was or what happened to her.
John was known as a religious man. His friend Cyrus Freer considered John a pillar of the Church and a solid citizen. Cyrus also noted that John was sometimes the only one present at the prayer meetings he held at the A.M.E Zion Church. When John died in 1907, the obituary in the New Paltz Independent stated that “He had reached the age of four score years and had been gradually failing of late. … [He] was noted for his cheerfulness and his hearty laugh,” as well as “his sincerity and earnest piety.” John was buried at the New Paltz Rural Cemetery.
Jacob Wynkoop, ca. 1908. Detail from a photograph of Civil War veterans at the New Paltz Rural Cemetery. Courtesy of Shirley Anson and the Haviland-Heidgerd Historical Collection, Elting Memorial Library.
Jacob, born on October 24, 1829, married a woman named Diana Rose in 1850. They had one daughter named Jane and, like her grandmother, known as “Jennie.”
During the American Civil War, Jacob enlisted in the 20th United States Colored Infantry; his recruitment papers described him as five-feet, five-inches tall. Before the war ended, the regiment saw duty in Louisiana, Texas, Florida, and Tennessee.
In 1883, Jacob and a group of local men signed a charter to establish the local arm of the Grand Army of the Republic (G.A.R.), a fraternal organization of both black and white Civil War veterans. The G.A.R. was one of the first advocacy groups in American politics, promoting and supporting a variety of causes, including voting rights for black veterans and lobbying for veterans’ pensions. Jacob was very active in the G.A.R., serving as their chaplain for more than twenty years and leading the group in parades and other appearances across the region.
Jacob worked as a carpenter throughout his life, building homes for his family and also for other families in the village of New Paltz, both black and white. The houses he built as lead carpenter on Mulberry, Church, and Broadhead Streets (many of which still stand today) have defined a neighborhood.
Newspaper clipping mentioning Jacob as captain of a black Republican club. New Paltz Independent, February 15, 1907. Courtesy of the Haviland-Heidgerd Historical Collection, Elting Memorial Library.
Jacob seems to have been at the forefront of black political engagement in New Paltz in the 1870s. To support the election of Republican candidate Rutherford B. Hayes to the presidency in 1876, a “colored Republican club” was formed by Jacob and Charles Moody, a black barber and farm worker who had emigrated from the South after emancipation. Black members of the community hosted political meetings in their homes and promoted Hayes in 1876, marching in weekly political parades that took place in New Paltz.
Jacob died on August 25, 1912, at age 83. His obituary in the Kingston Freeman noted his service during the war and mentioned his chaplainship with the G.A.R. Cyrus Freer reminisced in his “Death Book” that he and Jacob had been great friends and that Jacob had been not only a good carpenter, but also a well-read man and a good citizen, who remained “very useful” into his eighties. Jacob was buried in an area devoted to members of the G.A.R. and Civil War veterans in the New Paltz Rural Cemetery. An online exhibit about Jacob’s life and contributions to the community may be viewed by clicking here.