4 Jan. 1795–29 Aug. 1873
Nathan Winslow, the eleventh child of Caleb (1749–1811) and his first wife, Ann Perry Winslow (1755–96) of Perquimans County, was born on his father's Piney Woods Plantation in Perquimans. Thirteen months later his mother died, and the duty of rearing him fell on his sister Rachel, twenty-five years older than he, who married Jonathan White. Little is known of his early life and his opportunities for getting an education; suffice it to say that he was a well-informed man and wrote a good hand.
By the will of his father, Nathan was made joint owner of the home estate, and on the death of his stepmother, Peggy Scott Winslow, he came into possession of the whole property in 1833. It is probable that he added much by purchase to his land, for when the estate was sold in 1891, it turned out to comprise over 2,000 acres. This property is situated in the northern part of Perquimans County and to some extent in Chowan. In Nathan Winslow's day a large part of it was under cultivation and produced wheat, corn, oats, and other staple grains, fruits, sweet potatoes, and vegetables. The residence, which was destroyed by fire in 1921, was a two-story hip-roofed house with a wing extending back from the main building; the iron fireback in the large dining room fireplace bore the date 1768. The house was wainscoted throughout, the kitchen a detached building. In 1862, after the fall of Roanoke Island, Randolph Winslow (1852–1937), the grandson of Nathan, with his mother and his siblings took refuge there for several months.
On 29 Dec. 1819 Nathan Winslow married Margaret FitzRandolph (ca. 1781–3 July 1848), the daughter of Jacob and Elizabeth Pretlow FitzRandolph of Nansemond County, Va. The Winslows were the parents of John Randolph (1820–66), Rufus Kinsey (1822–43), Caleb (1824–95), and Margaret Ann Kinsey (1826-ca. 1830). Margaret FitzRandolph Winslow died at aged sixty-seven and was buried on Piney Woods Plantation. Remaining a widower for the rest of his life, Nathan Winslow lived alone on his plantation until the end of the Civil War. After the emancipation of the people he had enslaved, he rented the property to J. Hardy Ward but continued to reside with the Wards in his own house.
Winslow was a birthright member of the Society of Friends but was disowned because he owned and enslaved people; he continued, however, to attend meetings until his death. His father, Caleb, had manumitted the people he enslaved, so Nathan did not acquire any by inheritance. The story is that he bought an enslaved Black woman to keep her from being separated from her family. Having been "disowned" by the Society of Friends, he bought others and by the beginning of the Civil War owned a considerable number of people. He intended to free the people he had enslaved, and drafts of his will made in 1857 and 1858 provided that most of them be sent to Liberia; a few enslaved people were to be given the option of remaining in America. The Emancipation Proclamation precluded this intention.
Nathan Winslow was considered a rich man before the Civil War, but as a result of the emancipation of enslaved laborers he became impoverished. He owned a large estate but had no enslaved laborers to cultivate the land and no stock with which to till the soil. During the war a regiment of Union cavalry encamped on the place and used up his fences for fuel, killed his poultry, and stole his horses. Damage to the extent of $4,000 was done, and although the commanding officer gave him a receipt for the amount due, he was never able to collect it from the U.S. government.
As a farmer Winslow did not concern himself much about public affairs, but he did represent Pasquotank County in the state senate during the session of 1854–55. In those days he would drive to Hertford, about twelve miles from his plantation, in an old-fashioned gig drawn by one of his roan horses. After the war he spent several months each year with his son, Dr. Caleb Winslow, in Baltimore. About this time a small growth on one of his vocal chords affected his voice to such an extent that he could communicate only in a whisper. In the summer of 1873, after paying a visit to his Baltimore family, he took a sea voyage to Boston. On reaching Boston Harbor, he complained of pain in his chest. The ship's steward gave him some remedy and he retired. In the morning he was found dead in his bed. He was buried in the Friends' Harford Road Burying Ground in Baltimore.