Colonel Robert Bolling, sometimes called Robert Bolling, Sr., after he gave a son his own name, was a wealthy early American settler planter and merchant.
Ancestry and early life
Robert Bolling was the son of John Bolling and Mary Carie Bolling. He was named after his grandfather Robert Bolling; his grandmother was Anne Clarke. He was born at Tower Street, All Hallows, Barking Parish, in London on December 26, 1646. His father John, was one of the Bollings of Bolling Hall, near Bradford, England. Robert's ancestry could be traced to Robert Bolling, Esquire, who died in 1485 and was buried in the family vault in the church of Bradford. On October 2, 1660, at the age of fourteen, Bolling arrived in the colony of Virginia. In 1674, he married Jane Rolfe, daughter of Thomas Rolfe, the son of Pocahontas. They had one son, John Bolling. There is a strong possibility that they also had a daughter, Rebecca Jane, in 1675. A Rebecca Jane Bolling married Rev. James Clack. On the marriage notice her birth date is listed as 1675. The strongest support that she is Jane Rolfe's daughter is that Rebecca was Pocahontas's Christian name. Jane is said to have died shortly after the birth of John Bolling. John Bolling married Mary Kennon, daughter of Richard Kennon and Elizabeth Worsham, and they had seven children.
Second marriage and death
In 1681, after his first wife died, Col. Bolling married his second wife Anne Stith, daughter of John Drury and Jane Stith. They had the following nine children together. Source needed to substantiate John Stith had a middle name. He worked with a Thomas Drury as a young man and somehow learned the law. Perhaps Mr. Drury enabled Stith to study by access to his private legal book collection, Harvard being the only N. American college yet established in the 1660s and an English education being very unlikely for a former indentured servant such as Stith. This is the more probable origin of the Drury name in the Stith line. Also his wife Jane's maiden name was certainly not Gregory or Parsons as they were both previous husbands. One court record lists her as "Jane R Stith" but this might be a phonetic spelling for Aldridge. She was illiterate- left her mark in the record, not a signature- and so may have believed her name began with "R." There was, in fact, a Jane Aldridge listed in an early Charles City Co. record prior to her first known marriage to Mr. Gregory. No prior record of another Jane in the county with a last name beginning with "R."
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. The descendants of his second marriage are referred to as "White Bollings". As a merchant and planter, Bolling acquired a large estate. He was colonel of the militia and was a member of the House of Burgesses from Charles City County in 1702. Robert Bolling died on July 17, 1709, and was buried on his plantation Kippax, in Prince George Co., Virginia, where his tomb still stands. However, in 1858, his remains were removed from Kippax to the Bolling mausoleum at Blandford Cemetery in Petersburg, Virginia erected by his great grandson.
