Major John Fairfax Bolling (January 27, 1676 – April 20, 1729) was a colonist, farmer, and politician in the Virginia Colony. He was the son of Colonel Robert Bolling and Jane (née Rolfe) Bolling. His maternal grandfather was Chief Powhatan's grandson, Thomas Rolfe, the only child of Pocahontas.
John Bolling was born at Kippax Plantation, in Charles City County, a site which is now within the corporate limits of the City of Hopewell. He made his home at the Bolling family plantation "Cobbs" just west of Point of Rocks on the north shore of the Appomattox River downstream from present-day Petersburg, Virginia. (Cobbs was located in Henrico County until the area south of the James River was subdivided to form Chesterfield County in 1749.)
John Bolling married Mary Kennon (1679–1727), daughter of Richard Kennon and Elizabeth Worsham, on December 29, 1697. They had at least seven children, whose names appear in John Bolling's will:
- John Bolling Jr. (1700–1757) married Elizabeth Lewis in 1720. Later married Elizabeth Bland Blair (who was the niece of James Blair, the first president of The College of William & Mary) on August 1, 1728 and had at least nine children, including John Bolling, who married Mary Jefferson, the sister of United States President Thomas Jefferson.
- Jane Bolling (1703–1766) married Colonel Richard Randolph in 1714 or 1720 and had six children.
- Elizabeth Bolling (b. 1709), married William Gay of Scotland and had three children.
- Mary Bolling (1711–1744), married John Fleming and had eight children.
- Martha Bolling (1713–1737), married Thomas Eldridge in 1729 and had four children.
- Anne Bolling (1718–1800), married James Murray and had six children.
- Sarah Bolling (1727-1816), married Major Robert Davis and had one child.
Major Bolling served in the Virginia House of Burgesses from 1710 until his death.
In 1722, he opened a tobacco warehouse in what is now the 'Pocahontas' neighbourhood of Petersburg. William Byrd II of Westover Plantation is said to have remarked that Major Bolling enjoyed "all the profits of an immense trade with his countrymen, and of one still greater with the Indian."
John and Mary Bolling's descendants are the only descendants of Pocahontas, and include Edith Bolling Galt Wilson (the wife of U. S. President Woodrow Wilson), Percival Lowell, Harry Flood Byrd and Richard Evelyn Byrd.
- Henrico Wills & Deeds 1697-1704, p.96
- Pecquet du Bellet, Louise. "Bolling Family". Some Prominent Virginia Families. IV. Lynchburg, Virginia: J.P. Bell Company. pp. 304–314.
- Page, Richard Channing Moore (1893). "Randolph Family". Genealogy of the Page Family in Virginia (2 ed.). New York: Press of the Publishers Printing Co. pp. 249–272.
- Glenn, Thomas Allen, ed. (1898). "The Randolphs: Randolph Genealogy". Some Colonial Mansions: And Those Who Lived In Them : With Genealogies Of The Various Families Mentioned. 1. Philadelphia, Pennsylvania: Henry T. Coates & Company. pp. 430–459.
- Henrico Wills & Deeds 1697-1704, p.97