The second generation in my husband’s Wooldridge line is another John, the son of blacksmith John and his wife, Martha (possibly Osborne).

John Junior married (1) Elizabeth Branch, daughter of James Branch and Mary (possibly Ware?). We’ll take a closer look at the Branch family soon.

John Wooldridge was born c1705, likely in Henrico County, Virginia, where his family lived. He married Elizabeth, c1730, probably also in Henrico County. She was born c1710 and died after December 1755, when she witnessed a deed for her mother and brother. When John died in 1783 in Chesterfield County, Virginia, his wife was named as (2) Margaret (MNU).

John Wooldridge left a lengthy will, dated 16 November 1780, Chesterfield County, Virginia.

John Wooldridge is listed in the DAR Patriot Index as having given patriotic service, so likely served in some kind of town office.

Beginning with the third generation of the Wooldridge family, children began to migrate westward, as land was becoming more expensive.

John’s children settled in Bedford and Campbell Counties, Virginia, in addition to Bourbon, Woodford and Henry Counties in Kentucky (not shown on this map, as they formed after 1776.) These were all considered part of Virginia.

It was a time of change and the beginning of the westward migration. John Wooldridge lived to see the independence of the American colonies, but he had been long gone by the time his sons headed to Kentucky.

John and Elizabeth were the parents of ten children. The first six were probably born in Henrico County, with the remaining born in Chesterfield County, which was set off in 1749:

1. Richard, born c1731; died 1782 (Will Book 1:10), Campbell County, Virginia; married Elizabeth (MNU), c1760. Elizabeth appeared on the Campbell County tax rolls after that time.
2. John, born c1733; died c1782, Bedford County, Virginia; married (1) possibly a daughter of James Farley, as he named a grandchild Elizabeth Wooldridge in his 1779 will (2) Mary (MNU)
3. Mary, born c1737; died after 1780; married John Martin, before 1755
4. William, born c1740; died before 18 February 1817, Bourbon County, Kentucky, when his estate was appraised; married Mary Harrison, c1766.
5. Elizabeth, born c1745; died after 1780; married (1) John Wooldridge, c1771 (2) William Langston, before 1780
6. Edmund, born c1748; died between 28 April, when he wrote his will, and September court term, when it was probated in 1791, Woodford County, Kentucky; married Elizabeth Watkins, 22 August 1774, Cumberland County, Virginia. Elizabeth married (2) John Moss, 8 June 1792, Woodford County, Kentucky.
7. Verlinche, born c1750; reportedly married Daniel Elam, c1766, but I find no further information on this couple except they are said to have had quite a few children: Daniel, William, Robert, Thomas, Peggy, Verlinche.
8. Phebe, born c1752; died 1792, Chesterfield County, Virginia; married Richard Elam, c1770. Richard Elam died in Chesterfield County, Virginia, between 9 July 1791, when he wrote his will and January 1792, when it was probated.
9. Robert, born c1754; reportedly died 1801, Franklin County, Kentucky, but he isn’t found in 1790 or 1800; married Susanna Major
10. Thomas, born c1756; died between 22 October 1840, when he wrote his will, and January court term 1841, when the will was proved, Henry County, Kentucky; married Sarah Ann Barnes, after 1780 (2) Mrs. Agnes Kelly. Agnes survived Thomas, as she is named in his will.

John and Margaret were the parents of two children:

1. Martha, born c1762; married William Walthall, 29 October 1782 (bond), Chesterfield County, Virginia. She may have died soon as one William Walthall married there in 1787.
2. Hannah, born c1765; married Richard Elam, 21 October 1784 (bond), Chesterfield County, Virginia

My husband’s line is through this John’s son, yet another John, but for those who are descended from Edmond or Thomas, here are their wills:

Will of Edmund Wooldridge
Woodford County, Kentucky 1791 Will Book  A: 34-35
FamilySearch

In the name of God Amen. I Edmund Wooldridge of the County of Woodford do make and ordain this to be my last will and Testament in manner and form following

Viz. My will and desire is that after my just debts is paid that my Executors here after to be mentioned lay out all the money that shall or may be due my estate to the best advantage in likely young negroes and that I lend unto my wife during her life the third part of the negroes so purchased and also the (sance?) part of the negroes I have at present in my possession together with the third part of all my other personal estate, and also one third part of the tract of Land whereon I now live including that part of the plantation lying on the west side of Scotts Road. so as not to include? any of the  Clear? land on (?) east side of the said road I give unto my four Sons, Edmund, Samuel, Watkins and Powhatan four thousand acres of my best Land to be equally divided amonth them agreeable to quantity and quality.—I leave it in the power of my Executors to sell or exchange any part of my estate, Real pr personal as they may Judge necessary for the advantage of my estate. –And all my other estate both real and personal not before given away I desire may be equally divided amony my children both sons and daughters, when my Son Samuel shall arrive at the age of twenty one years or the whole or any part thereof sooner, if my Executors shall think Necessary & my will and desire is that if any of the negroes that my Executors shall think fit to let any of my children have before a division takes place shall die in that case the loss shall be made good to such child or children out of the remaining part of my estate before a General Division is made. It is my will that my Executors bind out each of my sons to some good trade when they respectively arrive at the age of sixteen years. And lastly I do appoint James Watkins Henry Watkins Thomas Wooldridge and Walthall Watkins as Executors of this my last will and testament. In witness whereof I have hereto set my hand and seal this 28th day of April in the Year of our Lord one thousand seven hundred and ninety one.

Edmund Wooldridge (seal)

Sign’d Seal’d & (Decreed?) to be the
last will & testament of Edmd Wooldridge
in the presence of
Wm (X) Hill
Thos Ray
Pageatten Coleman

Woodford County Sct September Court 1791
This will was produced in Court proved by the oaths of William
and Thomas Ray subscribing witnesses thereto and ordered
to be Recorded
Cave Johnson (?)

Will of Thomas Wooldridge, 1840
Henry County, Kentucky WB 7:284
FamilySearch

I Thomas Wooldridge of the County of Henry and State of Kentucky do this day make this my last will and Testament I having Spetial Trust and confidence in my Worthey friend James Hisle I appoint him my executor
2nd I do will and bequeath my son Edward Wooldridge my negro man Jack a Servent for life.
3rd I do will my two daughters Betsy Wingate & Mary (Pliner?) five Dollars in Cash each 4th I do will my beloved wife Agnes Wooldridge all the reside of my estate real & personal consisting mostly of two head of Horses one Cow and Calf together with my Stock of Hogs and Household & Kitchen furniture farming utencisls & together with my present crop of corn and Wheat. In testimony whereof I do set my jand and Seal this 22 of October 1840

Thomas (X) Wooldridge (seal)

George King
James Hisle

Henry County Court January Term 1841

A Writing purporting to be the last will & Testament of Thomas Wooldridge Decd wast this day produced into court and proven by two Subscribing witnesses thereto and ordered to be Recorded.

Edw Thomas C