The following data is extracted from Genealogy and Biography of Ontario County, New York.
The founder of this family, Nathaniel Oak(e) must not be confounded with Thomas and Edward Oak(e)s, the founders of the Cambridge-Malden family, or with the Welsh William, who founded the Worcester county family. As Nathaniel wrote his name, it was originally Oak or Oake. His son Jonathan added a final "s" and descendants of the fourth and fifth generations are about equally divided between the spellings Oaks and Oakes. Nathaniel Oak(e) was born about 1645, and died at Westboro, February 17, 1721. The following account of his immigration is inscribed in the family Bible of one of his greatgrandchildren :
"The grandfather of my mother, was a cabin boy on an English vessel bound to Boston. Nine miles from land the vessel foundered. All the ship's crew, except the boy whose name was Oaks, were lost. He, being a good swimmer, swam ashore. In his distress he solemnly promised the Lord if He would preserve him to get to land, the would never go onto the water again. This promise he sacredly kept. His wife, my great-grandmother, could never persuade him even to cross Charles River in a boat to Boston, he would always go around upon the neck. Thus he reached his after-home, poor and penniless, without even clothes to cover him, and as was then the custom, having no friends in America, he was bound out to earn his own living. His master sat him to work in a pitch-pine forest to pick up pine knots. In this employ be was attacked by a catamount, or wild cat, which he slew with a large pine knot. His master gave him the bounty the State paid for the pelt of this furious beast, with which he bought a sheep or two, which he let out to double. These sheep were all the property he began the world with when he became of age. He often said that while swimming to land he suffered more from hunger than anything else. When tired he would turn on his hack and rest. The above account I have often heard my mother and uncle relate."
He married (first), December 14, 1686, Mehitable, daughter of John and Ann Rediat, who was born in Sudbury, Massachusetts, in 1646, and died without issue, November 25, 1702. He married (second), May 20, 1703, Mary, daughter of Adam and Hannah (Hayward) Halloway and widow of Jacob Farrar, who was killed in King Philip's war in 1676. She was born February 25, 1682, and died after 1733. She survived her second husband, and married (third), July 2, 1722, Thomas Rice, by whom she had two children. Children of Nathaniel and Mary (Holloway-Farrar) Oak: 1. Nathaniel, June 7, 1704, died, probably June 5, 1783; married (first), February 20, 1727, Tabitha Rice, and (second), June 7, 1736, Keziah Maynard. 2. William, born February 18, 1706, died August 8, 1723, unmarried. 3. Hannah, born December 27, 1707, died March 3, 1807; married about 1728, Gershom Fay Jr. 4. Mary, born March 31, 1710, died April 4, 1805; married, February 20, 1735, Daniel Maynard. 5. Ann, born September 9, 1712, married about 1735, David Maynard. 6. John, born March 16, 1715, died in September, 1752; married, November 2 or 3, 1742, Susanna Allen. 7. Jonathan, referred to below. 8. George, born February 15, 1720, died after 1777; married (first), October 23 or 26, 1744, Lydia Eagar, and (second), June 12 or 13, 1765, Mary Bartlett. He settled in Rutland, and was one of the Lexington minute-men.
Source: Genealogy and Biography of Ontario County, New York