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Bolling arrived in the colony of [[Virginia]] at the age of fourteen on October 2, 1660.<ref>The Virginia Magazine of History and Biography, Volume 7, 1899, pages 352-353.</ref>  He married, in 1674, [[Jane Rolfe]] the daughter of [[Thomas Rolfe]] and Jane Poythress.<ref>The Virginia Magazine of History and Biography, Volume 7, 1899, pages 352-353.</ref> Her paternal grandmother was the Native American [[Pocahontas]].<ref>The Virginia Magazine of History and Biography, Volume 7, 1899, pages 352-353.</ref> Jane died around the time their only child, [[John Bolling]] was born<ref>A Memoir of a Portion of the Bolling Family in England and Virginia, Robert Bolling, John Robertson, Thomas Hicks Wynne, Chesapeake Book Co., 1868, page 19.</ref> on January 26, 1676 he married Mary Kennon and died on April 20, 1729. The descendants of John Bolling were termed the "Red Bollings".
 
Bolling arrived in the colony of [[Virginia]] at the age of fourteen on October 2, 1660.<ref>The Virginia Magazine of History and Biography, Volume 7, 1899, pages 352-353.</ref>  He married, in 1674, [[Jane Rolfe]] the daughter of [[Thomas Rolfe]] and Jane Poythress.<ref>The Virginia Magazine of History and Biography, Volume 7, 1899, pages 352-353.</ref> Her paternal grandmother was the Native American [[Pocahontas]].<ref>The Virginia Magazine of History and Biography, Volume 7, 1899, pages 352-353.</ref> Jane died around the time their only child, [[John Bolling]] was born<ref>A Memoir of a Portion of the Bolling Family in England and Virginia, Robert Bolling, John Robertson, Thomas Hicks Wynne, Chesapeake Book Co., 1868, page 19.</ref> on January 26, 1676 he married Mary Kennon and died on April 20, 1729. The descendants of John Bolling were termed the "Red Bollings".
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After his wife Jane died Robert married Anne Stith the daughter of John Drury Stith and Jane Gregory.  
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In 1681 Bolling married Anne Stith the daughter of Major John Drury Stith and Jane Gregory.<ref>''William and Mary College Quarterly Historical Magazine'', The Stith Family, Armistead C. Gordon, Volume 22, Number 1, July 1913, page 44.</ref> 
    
They had the following nine children together.
 
They had the following nine children together.
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