I will included all of the reseach I have on this matter. If you will please send me anything I don't have perhaps the answer will become clear.
PENELOPE married CHRISTOPHER CLARK about 1709 in Virginia. Their first child was born in 1710.
I've started with a "MASSEY" because this is probably the easiest to rule out.
CHRISTOPHER CLARK'S daughter AGNES Clark married BENJAMIN JOHNSON, who was a son of SIR WILLIAM JOHNSON and PENELOPE MASSIE JOHNSON of Scotland (Americans of Gentle Birth, vol I, pg 353, cited by McConnell McNaught 1979. This is probably how the MASSIE name came into the family references.
MCNAUGHT (pg 128) cites CARRINGTON, a well-known and reputable genealogist, who was descended from AGNES CLARK JOHNSON and also from THOMAS & RACHEL CLARK MOORMAN. In 1913 CARRINGTON wrote about the Moorman family tradition that three MASSIE women (two sisters and a cousin, or perhaps three sisters) were descended from a sister of the EARL OF SHAFTESBURY (SIR ANTHONY ASHLEY-COOPER 1621-1683) who had married a MASSIE. One of these descendants was SARAH MASSIE who married WILLIAM JOHNSON and was the mother of BENJAMIN JOHNSON, thus the mother-in-law of CHRISTOPHER CLARK'S daughter AGNES.
This seems to be the total extent of the MASSIE "connection" with CHRISTOPHER CLARK'S family. There is no evidence of any PENELOPE MASSIE who ever lived in Virginia (MCCONNELL 1979, MRS JACOB'S letter of 1980).
Although many think PENELOPE, wife of CHRISTOPHER CLARK was a JOHNSON, I do not. However, the case is much stronger for this theory than for the Massie theory.
I do not think PENELOPE was a JOHNSON. Her daughter was married to a JOHNSON. However, there was a PENELOPE JOHNSON. Some people think the proof is conclusive.
First, this PENELOPE JOHNSON was born in 1684 in New Kent County, Virginia. Christopher was most probably born in 1681.
Secondly, CHRISTOPHER CLARK'S second daughter was named RACHEL, not found in the CLARK family, but the name of PENELOPE JOHNSON'S sister.
Thirdly, this PENELOPE'S brother, THOMAS JOHNSON, recorded land in 1719 in the Register of St. Peter's Parish (pg. 17) right on CHRISTOPHER CLARK'S corner, and was a witness to the will of his (Thomas') niece, AGNES CLARK JOHNSON.
This sounds like fairly good proof and it may well be true that PENELOPE JOHNSON was the wife of CHRISTOPHER CLARK but here is another theory.
A BOLLING, BOWLING, BOWEN?
Many people think/thought that the fact that CHRISTOPHER & PENELOPE CLARK'S son is named BOLLING/BOWLING may be a clue to PENELOPE'S maiden name since it is fairly common at least to use it for a middle name of a son. This is a most unusual name for a son and might have some significance or give some clues to his mother's family.
Many people wanted PENELOPE to be the daughter of MAJOR JOHN BOLLING, a friend and neighbor of CHRISTOPHER CLARK'S. This would make PENELOPE a descendant of POCOHONTAS.
I discovered that in Virginia there are the "Red" Bolling's and the "White" Bolling's. I do not know whether or not there was any "put down" to being called a "Red" or a "White" Bolling or if it was just a way of defining each other. The "Red Bolling's" centered at least in recent years just West of Richmond in Petersburg. There was no Penelope that I could find in that connection.
A DIFFERENT BOLLING FAMILY
About 1985 I was in the Virginia State Library and found a book (#33019) by Todd Bolen & Lois Bolen Strange ("The BOLLING, BOWLIN, BOLEN Family in America before 1800"). The next time I went back it wasn't there. Thankfully, I had xeroxed the appropriate pages pertaining to our family.
Their theory is that PENELOPE was a BOLLING but not of MAJOR JOHN BOLLING'S family. She was related to a different BOLLING family. This one also had a RACHEL in it.
Here is the information I found in TODD and LOIS' book:
1) PENELOPE M. BOLLING (WILLIAM, GEORGE, WILLIAM II, WILLIAM I, THOMAS III, THOMAS II, THOMAS I) b. Louisa Co. VA New Kent VA m. abt 1709 to CHRISTOPHER CLARK
2) WILLIAM BOWLING (GEORGE, WILLIAM II, WILLIAM I, THOMAS III, THOMAS II, THOMAS I) d. bef 1754 Fairfax Co VA m. PENELOPE COOPER. Children: PENELOPE & WILLIAM, JR.
3) GEORGE BOWLING (WILLIAM BOWLING/BOWLIN II, WILLIAM I, THOMAS III, THOMAS II, THOMAS I) Methodist Clergyman d. 1736 Prince William Co VA m. JANE; Children: JOHN, WILLIAM
4) WILLIAM BOWLING II (WILLIAM I & ANN, THOMAS III, THOMAS II, THOMAS I) b. 1650 d. 1717 m. RACHEL LEWIS & 2nd to ELIZABETH of Prince William Co., VA. They lived in Fairfax Co. VA.
5) WILLIAM BOWLING I (THOMAS III, THOMAS II, THOMAS I) 1620 - 1691 moved to Philadelphia PA m. ANNE and 2nd to ELIZABETH
6) THOMAS BOLLING (BOULDIN) III (THOMAS II, THOMAS I) b. 1580 Warwickshire, England arrived in VA 1610 d. 1655 m. abt 1610 to MARY BOWLING (WILLIAM & MARY BOWLING)
7) THOMAS BOULDIN II (THOMAS I) b. Warwickshire, England
8) THOMAS BOULDIN I b. 1523 lived Shelborne, England
Below is more information from the book cited above by TODD & LOIS for these eight (8) people. But it is your decision whether or not our PENELOPE who married CHRISTOPHER CLARK came from this family. I'm inclined to think she did.
I would like you, my audience, to convince me conclusively one way or another. Please write and let me know your thoughts. Please include your email address and tell me if I can include it on this forum.
Number 6 above: THOMAS BOULDIN III and his wife MARY were the first BOULDIN'S to touch American soil. THOMAS BOULDIN III sailed for the new land on the sailing vessel "Swan" and arrived in Virginia in 1610.
THOMAS III was 30 years of age. He landed somewhere near, or in, the Jamestown Colony. The next we hear from him he has obtained a land grant some miles down the James River from Jamestown. It is worthy to note that the County between Jamestown and Elizabeth City, where he finally settled, was named Warwick as he was from Warwick England. Perhaps he named it thus.
Within ten years after his arrival the coast of the James River in this section was well occupied by farmers. Just fourteen years after he landed he received a land grant from the Virginia Council. It was located one and one-half miles up the Southampton River, in Elizabeth City County VA. The grant was registered Jan. 20, 1624 in Patent Book No. 1, Part 1, page 43 in General Land Office in the Capitol in Richmond VA.
He was mentioned again in the "Virginia Land Office (Patents & Grants) to TOBY SMITH, 650 acres in Warwick Co VA called Hunrperstow upon the head of Back River called SMITH'S Ford was adjacent to THOMAS FAULKNER & THOMAS BOULDING. Granted to said TOBY SMITH 2/14/1640.
The first settlers had come in 1607 and had built and called their settlement Jamestown. By spring of 1610 their number had shrunk to 40 men. No women at this time. They were prepared to return to England when met by these second three shiploads and persuaded to turn back.
Records show that THOMAS BOULDING was a seafaring man and made several trips to and from England.
THOMAS BOUGHLING/BOULDIN/BOWLING (1580-1655) when about 30 years old married MARY BOULDIN/BOWLING the daughter of WILLIAM BOULIN/BOWLING.
Number 2 above: WILLIAM BOWLING, the son of GEORGE BOWLING was the administrator in GEORGE BOLLING'S estate (1636) in Prince William Co VA. He was a Virginia Planter and a man of considerable wealth and influence in the Virginia Colony. He was an associate of CAPT LAWRENCE WASHINGTON and the aide to CAPT WASHINGTON in the political campaign that elected CAPT WASHINGTON to the Virginia House of Burgess.
WILLIAM BOWLING married PENELOPE COOPER. WILLIAM & PENELOPE COOPER BOWLING had no less than two children. One was PENELOPE BOWLING who married CAPT CHRISTOPHER CLARK. One was WILLIAM BOLLING JR. WILLIAM BOLLING married PENELOPE ASHLEY COOPER the daughter of ANTHONY ASHLEY COOPER and his wife DOROTHY MANNERS. WILLIAM BOLLING gave bond 1736 for the administration of the estate of GEORGE BOWLING.
Number one above: PENELOPE M BOLLING married CAPT CHRISTOPHER CLARK. (The M stands for MASSEY which might create more confusion. Also, perhaps, PENELOPE M was not the same person as our PENELOPE. I think this is the case).
CAPTAIN CHRISTOPHER CLARK, gentleman (1690 - 1754) was born in England. He came to America via Barbados and settled in Virginia.
He married PENELOPE BOLLING the granddaughter of the EARL OF SHAFTSBURG.
CHRISTOPHER CLARK joined the Friends (Quakers) in 1743 and was an overseer of Sugarloaf Monthly Meeting.
I have some more citations but the above should give you enough to check my theory. Please let me know what you find.
From: ken Poole firstname.lastname@example.org
Subject: Clarks and Bollings
Date: Saturday, 21 May 2011
I found your Christopher Clark interesting and your work-up very
good. The Clarks came into Anson County, NC very early and were on
the Pee Dee River.. Part of Anson became Montgmery Co., NC in time.
Some families with them were Bollings, Lightfoot, Moorman, Rush,
Bingham, Crawford, and others. These were early Quakers and Baptists,
and into large land holdings.
I looked at one work-up which has Clarks (very early) going back
into the Lightfoot family, who also used the name Bolling, and they
went back into a William Bolling in England. Lightfoots came into
Anson (CO NC)as well and settled near by a John Bolling m. Mary ___ who
settled there in 1758 . The Rush family also came into the area.
I was born in Montgomery Co NC and stem from most of these early
A William Bolden/Bowling lived in Gloucester Co adjacent to Augustine
Warner, lived on the same creek (source Mason). This Wm Bowling m. a Rachel
Lewis as his second wife and appears to be the grandparent of a John
Bolling m. Elizabeth Lewis (the girl next door seems likely). A
John Bolling was a Burgess in Gloucester Co in the early 1700s and
appears to me to be the fellow who moved into Chesterfield Co and
there died in 1757.
When John Bolling died in 1757 a Mr. Randolph wrote in the Richmond
paper that John Bolling was 5th in his seat. Meaning the 5th in a
line of Boldens or Bollings so he could not be the same man, a grandson
of a Robert or he would be 3rd in his seat.
I just found a note from Carol McCrite on http://gen.culpepper.com/ss/p10032.htm. She says her grandmother's research has our Penelope as a Bolling. She states that the Bolling name is found in surplus in almost every line of the Geogia families of Joseph Anthony and Elizabeth Clark (which is not proof in itself but a strong indication). Her grandmother had excellent records from family Bibles,letters, etc. Carol indicates that Penelope Bolling Clarke was the daughter of John Bolling and Mary Kenyon. John's father was Thomas Rolfe, the only child of John and Rebecca Rolfe who was known as Pocohontas. Pocahontas was the famous Algonquin Indian Princess who befriended Capt John Smith (http://gen.culpepper.com/historical/legends/indian.htm#Pocahontas).
This still does not prove anything at this point. It is still all speculation. PLEASE find me proof.