Revised 7/17/2017. Copyright @2017; The following Documentary Timeline has been compiled and created by Paul Rhetts. It may be copied for research purposes; but it may not be reproduced for inclusion in any printed or electronic distribution of any kind without the express written permission of the author. Any requests to use this information should be sent to Paul Rhetts,

Benjamin BOLLING (1734-1832) and (1) Martha PHELPS (1737-1767) and (2) Charity LARRIMORE (1746-1830)
s/o Unknown parents
d/o John PHELPS (1705-1775) and Mary C GIBSON (1709-1767)
p/o Benjamin BOLLING (1754-1819)

30 Jun 1734 Benjamin BOLLING born at Petersburg, Henrico, VA; became a Baptist Minister [Parents unknown: Perry County History/ Rugged Trail To Appalachia: Two books, the History of Perry County authored, in part, by Luther=Johnson, published by the Hazard, KY. Chapter of the DAR and "Rugged KY, =1978, share a common mistake. The "History of Perry County" 1832) [Benjamin 1734-1832 First Settler In Area Born Wilkes county, N. C. Son Of Major John Bolling And Elizabeth Blair. Wed First to Patsy Phelps And Then To Charity Larrimore Bolling] [PROVEN: Benjamin is NOT the son of Major John Bolling and Elizabeth BLAIR – not in “Red” or “Blue” family lines. [According to one researcher, while single Benjamin lived on his father's estate in Albermarle Co., the part later became Amherst Co. Benjamin first married Mary Patsy Phelps. Around 1760 they moved to Rowan Co., NC, then later on to Randolph Co. NC. Patsy died in childbirth. Benjamin then married Charity Larrimore. They settled near Esserville, near Flat Gap, Va. around 1791. They later went to NC because of Indian trouble but returned in 1806 with Daniel Boone as their guide to the "wilderness area" of Va. in the Flat Gap area. Benjamin is buried in the Flat Gap Cemetery in Flat Gap, Va. (This makes for a nice story but according to history, in 1799 Boone led his extended family from KY to Femme Osage country in Missouri; appointed "syndic" of district by the Spanish governor. In 1803 he was seriously injured in a hunting accident and relocated with Rebecca to a cabin on the farm of his son Nathan; Louisiana Purchase. In 1806 he appeared before the Federal Land Commission, seeking confirmation of his Spanish land grant hi Missouri. He was 72 years old at this time. He was given the land in 1814 and spent the rest of his life in Missouri. It is possible that he led a party of settlers into Ky. in 1806, but not likely.] [Town of Petersburg is South of the (Fluvanna) James River, and Henrico Co was a huge land
area, that became divided over & over until its present size. Powhatan Co, Fluvanna Co, Chesterfield Co were all carved from Henrico County after 1727. Goochland came in 1728 and was divided quickly into Cumberland Co, VA, which in 1777 was divided into Powhatan County. Later Petersburg became inside the new formed Dinwidde County.] [Birth Mother might be Elizabeth Lewis Bolling—ALTHOUGH DOUBTFUL]
29 Jun 1737 Martha PHELPS born at Albemarle, VA
1746 Charity LARRIMORE (Lattimore) born in Henrico, VA

20 Jun 1753 Benjamin BOLLING and Martha PHELPS married at Albemarle Co, Virginia [Benjamin and Patsy lived in Wilkes Co., N. C., then back to VA.. They had 9 children and then Benjamin and Charity had 10 children. (From Microfilm # 1502551 item 33 at the FH Library S.L. City Utah)] [[Family Data Collection Marriages, Edmund West] [Carrie Bradshaw (
My Bradshaws And Allied Families says Benjamin and Pattie Felts Bolling left Henrico Co., VA.=in the late 1750's and went to Wilkes Co, N.C., while PRICE says=Benjamin went to Albemarle Co., VA, where he md. Pattie and later went =to Rowan Co. N.C., in 1760. Pioneers of Adair County, KY by Menifee =Reed Cheek, Nashville TN, 1957 has same list of children as Carrie.] [Of Whom I Came, Etc. by Zelma Wells Price has a lot of misinformation]
Abt 1753 Benjamin BOLLING and Martha PHELPS moved to Rowan Co, NC

25 Apr 1754 Benjamin II BOLLING Rev. born at Randolph, Charlotte, Virginia; married Sally T. Hancock in 1772 at Spotsylvania, VA; died 1819 at Seagrove, Randolph, North Carolina

8 Oct 1754 Benjamin BOLLING listed in military service: DAR #P89535 SAR #89535 SERVICE: NORTH CAROLINA; Service Source: Colonial Soldiers of the South, 1732-1774, p728; Service Desc: Muster Roll of Col William Easton's Regt., North Carolina Militia, Granville Co, NC Oct 81754 (served for 9 mos.); Rank: Private (doc) [NC Revolutionary War Soldiers, Appendix p. 513] also lists Charity LARRIMORE and son Jeremiah (doc)
9 Jan 1756 son John BOLLING born at Rowan, NC (one source says Henrico, VA); married (1) _____ KENNON; (2) Pattie Mangum 12 Aug 1790 in Granville, NC; died 12 Mar 1836 at Wise, VA

9 Jan 1756 son James Thomas Powhatan BOLLING born at Chesterfield, Chesterfield, Virginia; m. (1) Martha Mary Jefferson 29 Jun 1760 in Goochland, VA; (2) Sarah Blevins 1776 in VA; died 7 Aug 1804 at Chesterfield, Chesterfield, Virginia (To date no documented evidence of James Bolling’s parents, birthdate or place has been found; census information suggests that he died between 1810-20 in Clay Co., KY. Judge Zelma Wells Price states that James Bolling was born 9 January 1756, Chesterfield (from Henrico) Co., VA (Ref. 1). The 1810 Clay Co. KY census information does state that he is over 45 at that time. We know of no earlier publication citing a different birthdate for James Bolling. Judge Price sets out in affidavits made by Mrs. Ara Janet B. (Bolding)
Stegall, 17 November 1958 and Martha Ellender (Ellen) Weatherbee Edmundson that James Bolding, born 9 January 1756, is the 20th child of John Bolding and his wife Elizabeth Blair (note spelling). She states that there were two Archibald’s, “…. one died young, and that would make 21 children in all.” Mrs. Stegall states that the information comes from …“very old and yellow (list) and almost crumbled but I still have it. I copy (sic) this from a copy my papa made years ago. So as not to handle the old copy too much.” Mary Caroline Bradshaw Bolin’s (Ref 2) My Bradshaws and Their Allied Families quotes the birthdate of 9 January 1757, Chesterfield Co, VA. Hattie L. Bolling (Ref 5) agrees that James Bolling b1756 was the 21st son of John and Elizabeth Blair Bowling. Other undocumented sources refer to James as being the son of Benjamin (1734), but continue to use the birthdate of 9 January 1956. Mary T. Brewer’s book, Rugged Trail to Appalachia (Ref 3) quotes Rev. John Jay Dickey’s (Ref 4) 1898 diary notes with Jason Walker Bowling, Benge, KY which we quote in part: “My great grandfather, Jesse Bowling, came to Kentucky in 1810. My grandfather, Elijah Bolling, was born at Lee County, VA, on Three Forks of Powell River in 1798, came to Perry County at 12 years old… My great great grandfather was Major John Bolling. He had 19 sons, one of these, William, married Martha Jefferson, a sister of Thomas Jefferson, president of the United States.” (Note: The Jesse Bowling to which Jason Walker Bolling/Bowling refers is the Rev. Jesse Bowling, s/o Benjamin Bolling (b 1734). Todd Bolen (Ref. 6) references “James b1756/mc1776 Sarah “Sally” or Mary “Polly” Blevens/Blevins - His father may have been Benjamin #110 or maybe John #380.” Benjamin #110 was born 1734 or b1740-50-1832/1 m1753 Patsy “Pattie” or Mary “Molly” Phelps 1737-1767- His father could be Benjamin #109 (Benjamin b1709/Charlotte Ward, or John #380 (John b1700-1757/l/w m1 1720 Elizabeth Lewis, m2 Elizabeth Blair).

9 Jan 1757 son William “Blackwater Bill” BOLLING born at Henrico, VA (one source says North Carolina); m. Sarah Fugate 1770 in Russell, VA; died 8 Jan 1838 at Cape Girardeau, Cape Girardeau, Missouri

1757 son Robert BOLLING born; died 10 Mar 1841 at Quicksand Creek, Breathitt, Kentucky

22 May 1758 son Jesse BOLLING Rev. born at Hillsboro, Orange, North Carolina; married (1) Polly GREEN 1776 in Wilkes, NC; (2) Mary Pennington 6 Jan 1785 in Wilkes, NC]; died 10 Mar 1841 at Quicksand Creek, Breathitt, KY; listed as a Rev and a Sgt in Rev War (one source says 21 Jun 1759 as birth date) (
Jesse Bolling b 22 May 1758 Hillsboro Co NC d 10 Mar 1841 Quicksand, Breathitt Co KY. He was a Primitive Baptist Preacher. He married 6 Jan 1785 in Wilkes Co NC to Mary Elizabeth Pennington b 8 Nov 1765 Grayson Co VA d 21 Mar 1842 Quicksand, Breathitt Co KY, d/o Micajah Pennington and Nancy Rachel Jones. (Source)) (Reverend Jesse & Mary (Pennington) Bowling were among the founders of what was earlier known as the "Bowling District" and later known as "Bowlingtown Community," of Hazard, Perry Co, KY. (In 1795, Jesse had become the Pastor of the Stoney Creek Church at Fort Blackmore in Lee County, Virginia.)
1760 son Justice (Justus) BOLLING born in Rowan Co, NC; married Martha Pattie BAKER 8 Jan 1782 at Wilkes, NC; died 1841 at Shelby Gap, Pike, Kentucky (one source says 1774 in Wilkes, NC) (
Justus Bolling (aka Justice) b abt 1751 Wilkes Co NC d 1841 Shelby Gap, Pike Co KY; m. 8 Jan 1782 Wilkes Co NC to Margaret Patricia Pattie Baker (aka Martha Pattie) b 1764 Wilkes Co NC; d/o John Renta Baker and Elizabeth Terrill. (Source))

1761 son Joel BOLLING born

1764 son David BOLLING born

1764 son Delaney BOLLING born at Rowan Co, NC [m. Patsy _____] died Feb 1853 in Mississippi

28 Apr 1766 dau Hannah BOLLING born at Salisbury, Rowan, NC; married Solomon OSBORNE 20 Jun 1786 in Pike, KY. Died 1852 at Indian Creek, Pike, Kentucky. They had six children: 1. Sherwood Osborn born 1788; married Louisa Collier on April 28, 1813 2. Benjamin Harrison Osborn born 1790; married Susannah Baker 3. Anna Osborn born 1792; married Buck Blankenship 4. Dicie Osborn born 1794; married Joe England 5. Hiram Osborn born 1798; married (1) Nancy Mullins in 1819; (2) Rebecca Bentley in 1866. Hiram died in 1892. 6. Hannah Osborn born 1800; married George Tacket in 1823 (Hannah Bolling b 1766 Salisbury, Rowan Co NC d 1852 Pike Co KY, m. 20 Jun 1786 Solomon Indian Creek Solomon Osborne b Dec 1765 NC d 9 Oct 1852 Indian Creek, Pike Co KY, buried Frank Tackett Cemetery, Long Fork, Shelby Creek, Pike Co KY, s/o Enoch Osborne and Jane Hash. (
8 Mar 1767 dau Elizabeth Blair BOLLING born in Salisbury, Rowan, NC [m. William Grancer Short bef 1799 in NC] m. Brittain WILLIAMS Jr; died 3 Mar 1819 at Flat Gap, Wise, Virginia (
Elizabeth Bolling b 8 Mar 1767 Buncombe Co NC d about 1805 TN m. before 1767 to Brittain Williams. Elizabeth Bolling m. 2nd to William Grancer Short b 15 May 1768 Surrey Co NC d 4 Jul 1851 Pound, Wise Co VA buried Flat Gap, Wise Co VA. William Grancer Short m. about 1809 to 2nd Mary Polly Birchfield. (Source))

8 Mar 1767 Martha PHELPS died [1767 Mar 8 — wife Patsy Phelps (Felts) died in Rowan Co, NC; due to complications arising from the birth of daughter, Elizabeth

1768 Benjamin BOLLING and Charity LARRIMORE married in VA [This story is believed to be incorrect: Wife of Benjamin Bolling was Elizabeth Christy/Crissie Larrimore born January 17, 1768 on the Edisto River in Southern Carolina (South Carolina) Ben married her there and their son Jeremiah was born there December 18, 1786. (This date is Wrong ) The father of Crissie Bolling was Squire Lariman. Jeremiah also write his father's name was John Benjamin Bowling born in old Virginny on June 30, 1732. His father was Issam (sic) Randolph whom he never seed sic) his mother was Polly Bolling who died at his birth. He was reared by his grandmother Betsey Bland. She first married his grandfather John Bolling who had died. Ben Bolling said that his grandmother gave him enough money to buy a farm in North Carolina on the Yadkin River. He lost it to the rebels during the War. He returned to Virginy to see his grandmother but she was dead. He found work at his sister Jane Jeffersons helping to build a new house. He earned enough money to recover his farm.
1770 son Levi BOLLING born; died 20 Jan 1832 at Hawkins, Tennessee
1772 dau Charity BOLLING born

1776 son Baxter BOLLING born

1778 son Barnett BOLLING born (one source says 9 Jan 1759 in NC; died 1830 Flat Gap, Wise, VA

11 Feb 1780 son Jeremiah BOLLING born at Hillsboro, Randolph, North Carolina (one source says SC not NC); married Sarah “Sally” WARD 1806 at NC [Note: There is a 15 year gap between his last child with Martha and his first child with Charity, leaving open the possiblity that there were children born to Benjamin and Charity before Jeremiah, or possibly even another marriage though I've found no hint of a wife other than Martha and Charity. Other children's names mentioned are Charity, Levi, Issac, Bennett/Barnett, Isham and James. [No documents linking them to Benjamin have been found] died 18 Feb 1870 Flat Gap, Wise, VA (many sources say Jeremiah is ONLY child of Benjamin and Charity) (
Jeremiah Bolling) Sarah Sally Ward b 1786 SC d 1845 Flat Gap, Wise Co VA. (Source))

1789 Benjamin BOLLING and Charity LARRIMORE arrived in Wise Co, VA, claiming all land you can see on Guest River, near Esserville
1790 Benjamin BOLLING listed on Randolph Co NC census (3 males under 16; 1 males over 16; 5 females (doc)

1791 Benjamin BOLLING and Charity LARRIMORE settled near Esserville, Wise, VA; soon became dissatisfied and moved back to North Carolina

1800 Benjamin BOLLING listed on Federal Census for Salisbury, Rowan, NC (1 male under 10; 1 male 26-44; 2 females under 10; 1 female 16-25 (doc)
1806 Benjamin BOLLING returned to Flat Gap, VA with friend Daniel Boone
??1810 Benjamin BOLLING listed on Russell VA tax list

1810 Benjamin BOLLING listed on Federal Census Falmouth, Stafford, VA [Males <10 3; Males 10-152; Males 26-44 1; Females <10 1; Females 10-15 1; Females 26-44 1](doc)
1820 Aug 7 Benjamin BOLLING listed on Federal Census Lebanon, Russell, VA [Males <10 1; Males45+ 2; Females 26-44 1; Females 45+ 1; Engaged in Agriculture 1] (doc)

1820 Benjamin BOLLING and Charity LARRIMORE joined son Jeremiah and moved back to Flat Gap, Weise, VA

1830 Benjamin BOLLING and Charity LARRIMORE listed on Federal Census Russell, VA [Male 80-89 1; Female 60-69 1] (doc)

1830 Charity LARRIMORE died in Flat Gap, VA

10 Jan 1832 Benjamin BOLLING died (age 96) at Flat Gap, Wise, Virginia (one source says 20 Jan, 1832) [Cemetery marker Wise, VA set up by Jeremiah BOLLING, incorrectly saying his father was the son of Major John and that he was born in Wilkes, NC, but actually in Henrico, VA:
BENJAMIN 1734-1832 FIRST SETTLER IN AREA BORN WILKES COUNTY, N. C. SON OF MAJOR JOHN BOLLING AND ELIZABETH BLAIR. WED FIRST TO PATSY PHELPS AND THEN TO CHARITY LARRIMORE BOLLING [Inscribed on tombstone, Flat Gap Cemetery, Wise County Virginia (also known as the Benjamin Bolling Cemetery) is located off of State Route 671 in Wise County, Va. It is about 8 miles from Pound.]

Of Whom I Came: From Whence I Came-Wells-Wise, Rish-Wise and otherwise by Judge Zelma Wells Price, January 1963.
My Bradshaws & Their Allied Families by Mary Caroline Bradshaw Bolin, 1964.
Rugged Trail to Appalachia by Mary T. Brewer
4) Rev. John Jay Dickey’s Diaries
Bollings by Hattie L. Bolling
The Bolling, Bowling, Bolen Family in America Before 1800 by Todd Bolen and Lois Bolen Stange, 2nd Edition 1997, Family Ref #270.)

Parents unknown — many theories  Birth 1. It has long been asserted that Benjamin Bolling, born June 30,1734, was the son of John Bolling and Elizabeth Blair Bolling. One of 19 sons. No proof of this anywhere. 2. Some assert he was the brother of Mary "Molly" Bolling who married "old" Andrew Baker but no one can prove who her parents were???? 3. Illegitimate son of Mary "Polly" Bolling, who died giving birth to Benjamin, and Isham Randolph. Whether this means General Isham Randolph or his son, Isham, b. in 1714, it not clear. General Randolph died in 1742, which would exclude him from being the father of someone born in 1744. The Randolph's and Bollings do have a long history though and General Isham Randolph was the brother of Mary Bolling Fleming's brother-in-law, Col. Richard Randolph. This Mary Bolling, sister of John Boling who married Elizabeth Blair and wife of Col. John Fleming is a possibility for Benjamin's mother. Col. Fleming died in 1756 but Mary died in 1744, possibly giving birth to Benjamin? This would make him 10 years younger than previously thought but age descrepancies happen all the time. This theory also says his name was John Benjamin Bolling, he was raised by his grandmother "Betsy" Bland (Elizabeth Blair Bolling m. Richard Bland after her husbands death in 1757) and that he had a sister named Jane Jefferson. The only Jane Jefferson found in this time period is Jane Randolph, daughter of Isham, wife of Peter Jefferson, and mother of President Thomas Jefferson. According to the theory, Benjamin was supposed to have returned to Virginia to visit his grandmother but she was already dead so he ended up working for his sister, Jane Jefferson, helping her to build a house. Elizabeth "Betsy" Bland died in 1775 and Jane Jefferson died in 1776 while living at Monticello, the home of her son, Thomas Jefferson. Construction began on Monticello in 1769 and lasted for many years, so Benjamin could have worked on it. But ... if he worked on Monticello wouldn't family tradition have mentioned that instead of just saying that he helped his sister build a house? Monticello was not just a house, it was the house of the President! However, if this theory is true, he would have been a half brother to Jane...(coincidentally, General Isham Randolph had a daughter named Dorothea. Dorothea is an asserted twin of Benjamin and daughter of John and Elizabeth Blair Bolling ... This little tidbit is fascinating!) The name descrepancy ("John" Benjamin Bolling) could explain why we can't find any records of him before 1800 or so. There are plenty of "John" Bollings in Va., NC and SC. Could Benjamin be one of them? Southern families used first names for legal documents even though people often went by their middle names. No documentation points in that direction with Benjamin though. The Randolphs, Bollings and Flemings lived within close proximity of each other so there is every possiblity that Mary could have had a close relationship with Gen. Isham Randolph - or any of his sons. Note #1: Grantee: Randolph, Thomas. Date: 9 February 1727. Location: Henrico County. Description: 400 acres on the south side of James River; begg. at Thomas Attkinsons or John Rights lower corner on the South side James River, opposite to Major Bollings plantation in his Island. Who is this Thomas? Some researchers list Gen/Col. Isham Randolph's first name as Thomas? Note #2: from Library of Va., Land Grants - Grantee: Randolph, Isham. Date 19 June 1735. Location: Goochland County. Description: 28 acres, 1 r., 28 po., being in James River opposite to Fleming’s Rock Castle Tract being an Island. Source: Land Office Patents No. 15, 1732-1735(v.1 & 2 p.1-522), p. 525 (Reel 13). Note #3: Grantee: Bolling, John. Date: 6 May 1727. Location: Henrico County. Description: 800 acres or the north side James River on the back of Mr. Fleming’s Rock Castle tract. Source: LVA Land Grants, Land Office Patents No. 13, 1725-1730 (v.1 & 2 p.1-540), p. 73 (Reel 12). On the Pocahontas Descendant chart at Pocahontas Descendants, David Morenus shows 8 children for Mary Bolling Fleming, although only 7 are named. Who is the other son? Conclusion: #1 If Benjamin was born in 1734 and his mother died at his birth, he can't be the son of Mary Bolling Fleming, who died in 1744 -but could be the son of another Mary Bolling and General Isham Randolph. But which Mary Bolling? Conclusion #2 If he was born in 1744, the illegitimate child of Mary Bolling Fleming, his father could not have been General Isham Randolph, who died in 1742, but could be Isham, the son of General Randolph. This Bolling/Randolph theory is supposed to come from some papers that Jeremiah Bolling wrote but I have not seen those papers. There is another Mary Bowling possibility. She married William Eatonin Stafford Co. Va. in 1935. I can't find any parents for her. Not sure if this is the same William Eaton in the Eaton's Militia Muster of Granville Co. NC in 1754. There is a Benjamin Bowling on the Muster also. Is he a son of this Mary Bowling born before she married William Eaton? 4. He is the son of Thomas Bolling/Boulding of the "Swan". The Bolling Family Association is leaning in this direction after DNA testing on Col. Robert Bolling's proven descendants. This Thomas Bolling emigrated to Maryland then to Lunenburg Co., Virginia. However, after searching all the Bollings in Maryland, (including a James that migrated to Va.) No link between the Maryland Bollings and Benjamin. 5. He is the son of Edward Bolling and a Slaughter woman. Edward is a son of Robert Bolling and his 2nd. wife, Anne Stith. No proof of a marriage for Edward anywhere. Nor any proof that this Slaughter/Bolling wife took her son Benjamin to NC where he married Charlotte Ward and later had Benjamin b. in 1734. This would make Benjamin a "White" Bolling and not a descendant of Pocahontas. 6. A reference to a will for a John Bolling at the LVA: Bolling, John. Date 1744 Source Ac 22483 (Personal Papers, Tighe) Will dated 30 November 1744 Will proved 13. March 1744/5 Note: Part of index to wills not listed in Virginia Wills and Administrations, 1632-1800 (Torrence). Collection: Virginia wills and administrations. No County listed and no other information. Is it possible Benjamin descends from this John Bolling? Does anyone know who this John Bolling is or have a copy of the will? 7. 1741 N.N. Land Grant May 15 Miss Mary Bolin, Prince William Co (formed from Stafford and Prince Geo. Counties in 1731) 330a adjoining land of Elzy, Keen and Carter (LVA N. N. Land Grants ~Blauser Card #188). Does anyone know who this Miss Mary Bolin is?
1. Benjamin was supposed to have married a Martha "Patsy" Phelps on____ in Albemarle Co., Va. Does anyone know where proof of this can be found? Who were her parents? Two references at the LVA to a Phelps family in Albemarle Co: Patent: Grantee: Phelps, James. Date 16 August 1756. Location: Albemarle County. Grantee(s): Phelps, James and Phelps, William. Description: 400 acres on both sides of a branch of Wreck Island Creek. Patent: Grantee: Phelps, James. Date 16 August 1756. Location: Albemarle County. Grantee(s): Phelps, James and Phelps, William. Description: 400 acres on a western fork of Wreck Island Creek. Anyone have any further information on this family? 2. His second wife was Charity Larimore. According to the Bolling/Randolph theory, Benjamin married Charity/Chrissie/Elizabeth on the Edisto River in SC and they had their son Jeremiah there. Is there proof of Jeremiah's birth or his marriage to Sarah "Sally" Ward.
Siblings - the "Blue" Bollings
There are 7 proven descendants of John Bolling and Elizabeth Blair Bolling. Those 7 are "Red" Bollings, descendants of Pocahontas. There are 7 other "Red" Bollings that died young. There are 12 "Blue" Bollings, whose ancestry is unknown at this time. 1. Meotaka 2. william - cousin of Benjamin?, son of Thomas Bolling and Elizabeth Gay? or son of Anne Bolling and James Murrary? 3. Elizabeth - cousin of Benjamin? daughter of Thomas Bolling and Elizabeth Gay? (twin of William?) 4. Jared 5. Martha - cousin of Benjamin? daughter of Martha Bolling and Thomas Eldridge? 6. Dorothea (with twin 7. Benjamin) - actual daughter of Isham Randolph and half sister to Benjamin? 8. Jane - actual daughter of Isham Randolph and half sister to Benjamin? 9. Rodney 10. Rolfe - cousin of Benjamin?, son of Martha Bolling and Thomas Eldridge? 11. Powhatan - cousin of Benjamin, son of Robert Bolling and Mary Burton? 12. James - cousin of Benjamin, son of Anne Bolling and James Murray? Is it possible that all but Dorothea and Jane could be grandchildren of John and Elizabeth Blair Bolling and probably 2nd cousins of Benjamin? Possibly they all lived with John and Elizabeth at one time or another and people assumed they were all their children? Dorothea and Jane look to be legitimate children of Isham Randolph and his wife Jane Rogers, and therefore 1/2 sisters of Benjamin. No explanation for linking Meotaka (unless she was daughter of John and his 1st wife, Elizabeth Lewis), Rodney or Jared to Benjamin. In Samauel Bollings bible, he says his parents are William Bolling (son of John and Elizabeth Bolling Blair) and Amelia Randolph (daughter of Richard Randolph of Anne Meade). William Bolling, son of Thomas Bolling and Elizabeth Gay, did marry Mary Randolph (daughter of Richard Randolph and Anne Meade) but her name was not Amelia and they did not have a son, Samuel. According to research done by A. D. Smith, of SC, Samuel does descend from a William Bolling but he and possibly William Bolling was the son of James Bolling/Boulding of Pittsylvania Co. Va. No connection for him to Benjamin. These Bollings may be descendants of Thomas Boulding of the "Swan.” In a letter from Hosea Bolling (Jeremiah's son, Benjamin's grandson) to Jason Walker Bolling, Hosea says that his grandfather had a brother named Justice and that he "saw the two old men together" numerous times. Because Justice was so much older than Hosea's father, Jeremiah, could Hosea have mistakenly thought he was a brother to Benjamin instead of a half brother to his own father, Jeremiah? Justice was probably a son of Benjamin from his 2nd marriage but without documentation it's just another assumption.

Document written by Jeremiah Bolling Sr.in1853. Wise Co., VA Death Records, Book 1, Page 12 Line 14: Jeremiah Bowling died February 26, 1870, Widow, born South Carolina, age: 88 years 2 months and 8 days, Parents: Benjamin and Crissie Bowling, information given by Jesse Bowling, son. Posted by Nancy Clark Brown February 27, 2000" It my conclusion that Benjamin Bolling was born out of wedlock, why else would he take his mother's surname? Discussion welcome. Of course, the statement is not true. Mary (Polly) Bolling, the daughter of Elizabeth Bland, was not born until 1744. Benjamin's birthdate may be in error, but probably not by the 25 to 30 years necessary. The 1830 Russell Co., VA census lists Benjamin as between 80 and 90 years old, suggesting that he was born in the decade of the 1740s. Admittedly census ages aren't very reliable either. Even if his birthdate was between 1760 and 1765 so that Polly could have been his mother, he would scarcely have had time to grow up and move to a farm in North Carolina before Betsy Bland died in 1775. Also, how would he have fit in his Patsy Phelps family? Elizabeth Blair Bolling married Richard Bland after 1757 now her have child NO OK, if Jeremiah's 1853 statement is not true, is it authentic? The interesting aspect of this question is that even though the relationships and timing in the statement are garbled, Jeremiah named a number of individuals who in fact existed in or near the Bolling family (Mary Bolling, Betsy Bland, Isham Randolph, John Bolling, and Jane Jefferson). How would Jeremiah, a backwoods farmer living 300 miles and 100 years from these persons, have known all their names? In either case, why would he have extracted those names and concocted the statement? Was there a "blue" Bolling controversy raging in the 1850s? If he had done so, why wouldn't he have made his statement more consistent with the historic facts of the Bolling family? "For instance, a more consistent roots story might have been that Benjamin was the illegitimate son of Mary Bolling Fleming and her neighbor Isham Randolph. Born in 1744, Benjamin was taken in by his Uncle John Bolling when his mother died in August of that year. After John's death in 1757 and his aunt's subsequent remarriage to Bland, Betsy sent him to live on family property in North Carolina. He returned to Virginia in 1775 to find that his aunt had died, so he found work on one of his nephew's (son of Jane Jefferson) houses (He had several, not just Monticello). Could have happened; more consistent with historic fact as I know it; It seems more likely that Jeremiah got those names and the story framework from Benjamin. Jeremiah may have garbled the story. Benjamin may have made up a roots story to explain a missing background. (This would fit with the orphan background being explored by Lucie Fritz.) He must have been familiar with the Hopewell area and at least aware of all the individuals named, even if he didn't know their chronological relationships. All of the discussion of Jeremiah's statement assumes that it is authentic. Its contents point to a knowledge of a Bolling family in Hopewell, VA that one would not expect in the rural mountains, however. It suggests that there was some real connection between the John Bollings and Benjamin, whether familial or not. What was that connection?

Benjamin Bowling was a Melungeon and a close friend of Christopher Gist, a famous backwoods frontiersman. Benjamin's wife, Patsy Phelps was also a Virginia Melungeon and her mother was believed to have been a "Gibson". Benjamin settled on the Pound in now Wise County, Virginia about 1789. He and Patsy had 7 children there. When Benjamin, 1734, left North Carolina to return to Virginia he moved to Flat Gap in what is now Wise Co., VA. near the Kentucky and Tennessee borders. He died there in 1832 at age 98 and is buried in the Bolling family cemetery there. His second wife, Charity Larrimore whom he married after Patsy Phelps (Jesse's Mother) died in childbirth on 8 Mar 1767, is buried beside him. Benjamin and Charity had Jeremiah and possibly other children. This Jeremiah was the great-great grandfather of Pennington cousin Rev. C. Glenn Bowling, and is also the ancestor of E. Watson Bolling, author ot "The Bolling Descendants of John Rolfe and Pochahontas. Benjamin and Patsy lived in Wilkes Co., NC, then back to VA. They had 9 children and then Benjamin and Charity had 10 children. (From Microfilm # 1502551 item 33 at the FH Library S. L. City Utah) It is believed that the Bollings moved to NC between the years 1730-1789 from eastern Virginia. It was recorded in the first Federal Census that Benjamin Bolling, son of John and Elizabeth lived in Wilkes Co., NC in 1770. When Benjammin settled in what is now Wise County, Virginia, there were no roads, only Indian trails and animal paths. He settled in an area now known as Esserville, Virginia. An old chimney stood for many years which was believed to have belonged to Benjamin. It was located where the Rocky Forks empties into Guest River. Upon his arrival it is said that he declared, "all the land I can see is mine," and thereby became a land owner or squatter. It has been said that Benjamin believed that to live in the mountains, walled in, would make him free from religious and political examination. Benjamin, as all white settlers, feared the Indians, although he was never attacked. In this particular area, he felt that he was fairly safe, however, incidences regarding a family by the name of Roberts was said to have influenced Benjamin's return to North Carolina. These incidences were in regard to Indian raids involving this family and others. The Roberts family and some of his in-laws had unknowingly moved and settled within five miles of chief Benge and his tribe. This was a nearby area now know as Robert's Branch. It was said that Robert's small son had seen some Indians nearby. He told his father about it and said that if they should come that he was going to hide under the trunk of an old tree, under the branch, where the water had washed the dirt from around it. Roberts gathered his sons-on-law for a battle with the Indians. The Indians attacked at night. It was said that Roberts yelled, "why don't you wait until daylight and fight like white men." They said the young Roberts boy did just as he said and hid under the trunk of the tree near the branch. The Roberts dog attacked an Indian and pulled him over the tree trunk where the boy was hiding. Apparently the Indian did not see him. The Roberts man was killed during the attack. The family buried him under a large chestnut tree. They cut the tree and scattered chestnut burrs so the Indians would think they had cut it for the chestnuts. It is said that the first raid Chief Benge's Tribe made was either in Russell or Scott County. Two girls were captured and taken back to the tribe. The girls, they said, kept a keen eye on the way and later escaped. they told that they hid behind a fallen tree and that the Indians came so close looking for them that they could hear them talking. They arrived safely home. The last known raid that Chief Benge, the infamous eighteenth-century Cherokee warrior (also known as Captain Bob Bench) and his warriors made was in Southwest Virginia in 1794. They raided and burned the Peter and Henry Livingston homes on Holston River, capturing two of the Livingston women. They traveled northward through an area called Wildcat, East Stone Gap, Powell Valley, across Stone Mountain turning right at Hoot-owl Hollow. Jess Brock (1751-1843) organized a posse and went after the Indians. They took a shortcut across the High Knob Mountain and waited for Chief Benge. On the way to High Knob, an area now called Ice Plant Hallow, near a large rock, Jess and his possee killed Chief Benge. The rock is now called Benge Rock. The Livingston women were rescued. It was believed at that time that Benge's Tribe was located at the head of the Cumberland River in Kentucky. The tribe was thought to have migrated back to the Smoky Mountains in Tennessee. They had heard that Benge had a half brother, who was said to be the chief of a tribe there. Dorathea and Benjamin were said to have been twins. Benjamin was a Baptist Minister.

Benjamin Bolling moved from North Carolina in 1794 and settled about two miles north of present town of Esserville, on state road 620. One son, Jeremiah, then a small boy, and his wife accompanied him here. He lived here in a small cabin he built, for two years, when he sold his claim to another homeseeker and moved back to North Carolina. In 1810, or thereabouts, Jeremiah Bolling was married to Sally Ward of Georgia, and remembering the Cumberland Mountains decided to seek hunting ground and a home in the wilderness. So he set out, accompanied by his father, then very aged, and established himself on a claim on the South (or Lick) Fork of the Pound. Here two children were born and died and were buried on a hill back of the house in coffins hewn from poplar logs. Here he planted the first apple trees ever set out in Wise County. He had carried the scions across the mountains from North Carolina, in a gourd, which his father had used to carry powder in during his life as a soldier in the Revolution. This gourd is still in the possession of Benton Bolling, a great-great-grandson of the soldier, and great-grandson of Jeremiah. Here also, Jeremiah Bolling built a two room log house, intending to make it his home till death. But death caused him to change his mind. After the two first-born died, his wife was no longer satisfied there in sight of the little graves and he sold his claim here and moved across the dividing ridge and settled on the head of North Fork of Pound at present Flat Gap. Here he reared a large family, and here he died after a long life of struggle with the hardships of the wilderness. After he had established his home at Flat Gap he went far back on the slope of Pine Mountain and cleared up a small field and planted it in corn every year as long as he lived, but never made any attempt to harvest the crop. This field was planted to attract bear, deer and other game to the field where he would shoot his supply of meat. This field, now grown up in undergrowth in a wild uninhabited part of Pine Mountain is known as the "Jerry Field." 

The First Settlement of Benjamin Bolling  
: Five miles southwest of Wise. On State Road 620. East side, fifty yards from highway. Three miles north of Esserville.
Date: 1794.
Owners: Settled by Benjamin Bolling. Sold by Bolling to an unknown settler. Surveyed by Alexander Gray. Major Harvey Gray 1880-1915. Daniel Joseph Bolling 1915-1937.
Description: Described by descendants of Benjamin Bolling as a small one-room round-pole cabin.
History: Benjamin Bolling came from North Carolina in 1794 and settled just south of the mouth of Rocky Fork of Guest River. While living here, Mrs. Bolling was attacked by a panther at the spring one morning and she fought the animal off with a piggin until her husband ran to her rescue and shot the panther. After living here about two years, Bolling sold his claim for a rifle gun and two hound pups and went back to North Carolina. Later he returned with his son, Jeremiah Bolling, and settled on the Pound.  
The Bolling Powder Gourd  
: On the Pound-Flat Gap Road. Three miles east of Flat Gap at the home of Benton Bolling.
Date: About 1772.
Description: Ordinary yard or garden variety of gourd. About 10 inches across bottom (blossom end), flat, with handle (stem) cut off about three inches long, into which powder was poured or loaded into rifle. It is highly polished by age and is chocolate brown in color.
History: Benjamin Bolling was a soldier in the American Army of the Revolution. He prepared this gourd to carry his powder in so as to keep it dry. He prepared a deer skin bag or covering for the gourd to protect it from breading, and this covering is still on it. When he made his second and final journey into what is now Wise County, to establish a home, he carried a few scions in this powder gourd tied to the horn of his saddle all the miles across the mountains from North Carolina to the head of the Lick Fork of Pound, where he used them to plant the first orchard in Wise County. That was about 125 years ago and some of the trees are still living and bear annual crops of fruit. On Benjamin Bolling's death in 1835, the gourd fell to his son Jeremiah Bolling. He faithfully preserved it until his death about 1860, when it became possessed by Amos Bolling, Jeremiah's son, and his son, John, fell heir to it and at his death in 1935, it came into the hands of his son, Benton Bolling. It has been used in recent years to store bean seed and other garden seed in.
Source of Information: Benton Bolling, William Bolling. Notes furnished me by the late William D. McNiel.

According to Harley Tucker Bolling in his book,
The Bolling Family of Eastern Kentucky, Benjamin was the son of Jonathan Bolling II and Elizabeth Blair. He attributed the following children to Benjamin and his two wives:
    Five other people were listed as possible children including: Charity, Bennett, Isaac, Levi, and James.