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The Bolling family is of ancient English origin. Robert Bolling, Esq., during the reign of King Edward IV, possessed the elegant home of "Bolliing Hall" near Bradford in Yorkshire. It is from Robert that the Virginia family claims its descent. Robert Bolling was the son of John and Mary Bolling of "Bolling Hall" of the parish of All-Hallows, Barkin Parish, Tower Street, in London. He was born 25 Dec 1646 and arrived in Virginia on 2 October 1660. In 1675 he was married (first) to Jane Rolph, daughter of Lieut. Thomas Rolph by his wife Jane Poythress and granddaughter of Princess Pocahontas (wife of John Rolph), whose father was the Indian emperor, Powhatan. He was married (second) to Ann Stith, daughter of John Stith. Robert died at Kippax in Prince George County, Virginia on 17 July 1789.
Issue of Robert and Jane Bolling:
- John Bolling of "Cobbs" was born 27 Jan 1676, died 20 April 1729, member of the House of Burgesses in Virginia. He was married to Mary Kennon, a daughter of Dr. Richard Kennon of Conjureas Neck, Virginia. Issue:
- John Bolling, Major, born 20 January 1700, died 6 Sept 1757. He was a member of the Virginia House of Burgesses for nearly thirty years. He served as a Lieutenant of Chesterfield, commander of the militia and Judge of the County Court. He was married (first) to Elizabeth Lewis, daughter of John Lewis of Gloucester County, a member of the Council and married (second) on 24 Aug 1728 Elizabeth Blair (died 22 April 1775), daughter of Dr. Archibald Blair. Colonel John Bowling owned land on the south side of the Fluvanna River; his land grants included land on both sides. He was born in 1700, a grandson of Robert Bolling, the emigrant. John Bolling served as county-lieutenant in Chesterfield County, justice of the peace and for 30 years a member of the House of Burgesses. Robert Bolling was married to Elizabeth, the daughter of Dr. Archibald Blair, also a member of the House of Burgesses. Between 1740 and 1745 John Bolling entered 20,000 acres of land in the counties of Amherst, Buckingham, Appomattox and Campbell, for himself and his sons. Bolling Creek was located in Amherst County, south of Lynchburg. In 1743 he entered for Archibald Bolling, his son, 600 acres of land on Opossum Creek, of the Fluvanna River. In 1790 Robert and Mary Bolling of Chesterfield County sold to Robert Cheatham of Campbell County, 195 acres of land on Bolling Road along Reedy Creek, opposite the mouth of Pigeon Run. This was the dividing line of the old patent, between Thomas and John Bolling. Issue:
- Jane Bolling (1703-1766) married in 1720 Colonel Richard Randolph of "Curles". Issue:
a. Thomas Bolling, Major of "Cobbs" was born 18 Jul 1735 at Varina, Virginia, and died 7 August 1804. He studied law at Williamsburg, Virginia under Robert Carter Nicholas and established at Cobbs in 1812 the first institution for teaching deaf mutes in the United States..
b. John Bolling of "Chestnut Grove" born June 1737, married Martha Jefferson, a sister of Thomas Jefferson, President of the United States. Issue:
- Martha Bolling married Fielding Archer.
- John Bolling married Miss Kennon.
- Edward Bolling died 1835, married Dolly Payne.
- Mary Bolling married Edward Archer.
- Robert Bolling married Jane Payne.
- Archibald Bolling was born 21 May 1806 in Bedford County and died there on 22 May 1862. He married (1) Sarah, the daughter of Colonel Archibald Cary of Empt Hill; (2) Jane Randolph, a cousin of John Randolph of Roanoke; (3) Catherine Payne and a 4th time. Archibald had two homes, Red Oak and Retreat which were located on the line between Buckingham and Campbell Counties. He died in 1829 leaving his fourth wife land divided by the Richmond Road until it intersected with Joel McKinneys line. The lands adjoining David Robertson, Robert Franklin, McKinney, William Ferbush and Henry Christian he divided between his daughters, Sarah Megginson and Ann E. Cabell and between his grand-daughters, Pocahontas and Virginia (children of his deceased daughter, Elizabeth M. Robertson), and his sons John R. and Blair Bolling. Issue:
- William Holcombe Bolling, Judge, married Sallie White.
- Harriet Bolling married Mr. Waddell of Mississippi where they removed.
- Mary Jefferson Bolling married Mr. Tueslery, a German, leading a medical missionary to Japan.
