Bolling married twice. In 1674, Bolling married
Jane Rolfe, daughter of
Thomas Rolfe, the son of
Pocahontas. Jane Rolfe Bolling is believed to have died in childbirth, but this was also the year of
Bacon's Rebellion. The firstborn son John Bolling survived and became a wealthy planter and legislator (as did his half-brother mentioned below), as well as married Mary Kennon, daughter of Richard Kennon and Elizabeth Worsham, who bore six children. In 1681, after his first wife died, Col. Bolling married his second wife Anne Stith, daughter of John Drury and Jane (Gregory) Stith. They had five sons and two daughters together: •
Robert Bolling Jr. (January 25, 1682–1749), succeeded his father as burgess, and also served as the Clerk of the Prince George County Court by 1710. On January 27, 1706 he married Anne Mary Cocke, daughter of Richard Cocke and wife Elizabeth and paternal granddaughter of
Richard Cocke and wife Mary Aston. His grandson
Beverley Randolph, became
eighth Governor of Virginia. Robert and Anne were also the great-grandparents of Anne Custis – wife of CSA General Robert Edward Lee. • Stith Bolling (1686–1727), married Elizabeth Hartwell and had sons named Robert, John, Stith and
Alexander (who like his uncle but unlike his father, continued the family tradition of legislative service). • Captain Edward Bolling (1687–1710), married Ms. Slaughter and died of
smallpox at sea. • Anne Bolling (1690–1750), married Robert Elam, Senior. • Drury Bolling (1695–1726), married Elizabeth Meriwether. (Elizabeth's brother Nicholas Meriwether was a great-great-grandfather of Captain
Meriwether Lewis the explorer.) • Thomas Bolling (1697–1734). • Agnes Bolling (1700–1762), married Richard Kennon. The descendants of Robert Bolling's first marriage are sometimes referred to in family history forums as "Red Bollings" due to the Native American lineage of Jane Rolfe's grandmother Pocahontas. These "Red Bollings" include prominent descendants such as
Edith Bolling Wilson, wife of U.S. President
Woodrow Wilson. Bolling's great-grandson,
Robert Bolling, was one of the most prolific poets in colonial Virginia, as well as served in the House of Burgesses. Yet another Robert Bolling published a genealogical history of his family in 1868. The descendants of this man's second marriage are sometimes referred to as "White Bollings". ==Death and legacy ==