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William Holloway
Born 1730? ?Lyminster, Sussex, England
Died 1792 or 1793 Caroline Co. VA

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?Father
?Father
SPOUSE CHILDREN
Mary? Carter or Mary Smith

m. 1749?
?England
b. 1730?
?England
d. 1770?
?Caroline Co. VA
Frances

b. 1750
?England
d. 1799?
Caroline Co. VA
George

b. 1751?
Lyminster, Sussex, England
d. 1817
Culpeper Co. VA
John

b. May 25, 1761
England
d. Apr 15, 1823?
Clark Co. KY
Clarissa Jane

b. Jun 18, 1763
?England
d. Apr 17, 1847
Henry Co. KY
William "It is believed he came to Culpepper Co., VA with his children, from England" and died in Caroline Co. VA about 1792 or 1793, according to a memorial of a son of grandson John Alexander Holloway, Edward M. Holloway (1826-1907). [Find-a-grave, memorial of Edward M. Holloway, #57472710].
Caroline County Virginia was formed in 1728 from parts of Essex, King and Queen, and King William counties (see present day map for location).
Culpeper County Virginia was formed in 1749 from Orange Co. as one of the larger counties in VA, lying between the Blue Ridge Mountains to the west and Rappahannock River to the south and east (see present day map for location).
William's wife may have been a close descendant of Robert "King" Carter, a Caroline Co. VA landowner, and before the county was created, a council president and the acting Governor of Virginia in 1726 and 1727 when Governor Hugh Drysdale went to England. Carter died in 1732, when his heirs were listed as the absentee owners (planters) in Caroline Co. with John Adams as the "overseer". His heirs continued to own land there in 1743 with Henry Bell overseeing [Campbell, pp. 380-381].
In 1710, a John Holloway "leased [from the Crown] for a term of 500 years a tract of 2,660 acres in the section which became Drysdale Parish across the Rappahannock-Mattapony watershed from the headwaters of Peumandsend [Creek]". This was likely the John born 1670 and died after 1720, who was the son of George Holloway II (1638-1688). Then Holloway sold the lease to Robert "King" Carter "of Lancaster for seven pounds sterling and six Negroes". Carter never lived on the property but "he and his heirs maintained a plantation there for many years with an overseer in charge" [Campbell, p. 318].
As late as 1757, the heirs of Robert "King" Carter owned land in Caroline Co. but still had "never resided on their Caroline plantation". That year the sole schoolhouse in St. Mary's Parish was mentioned as being on the Carter land "on Peumendsend [creek] between Port Royal and the Bowling Green" and was apparently "a free school for the children of the overseer and other freeholders nearby" [Campbell, pp. 318, 442]. Son George probably would have just started his schooling by this date.
Possible brother Nathaniel was possibly the soldier in a regiment to defend the state in 1762. Afterwards he may have married Mary Eubank, having a son born in 1781. In 1772, Nathaniel Holloway, a Baptist preacher and a John Partlow (1736?-1789) were arrested because Holloway was allowed to preach at Partlow's residence. The testimony of Nathaniel's wife, Mary, was not accepted because she was a Baptist [Campbell, pp. 226, 283].
St Mary's Parish bordered the Rappahannock River to its north and Drysdale Parish to its south. Map of Caroline Co. drawn in 1751 shows what were previously St. Mary, Drysdale and St. Margaret parishes [Louisa Co. VA Genealogy, website]. Geographically, Culpeper Co. had previously been a part of Spotsylvania Co.. The only church in St. Mary by 1760 was the Mount Church on the Rappahannock north of Port Royal [Campbell, p. 430].
Daughter Clarissa married Samuel Hill. They had a son Henry who, on Sep 14, 1816, married cousin Elizabeth Holloway in Clark Co. KY. She was the first daughter of William's son John [find-a-grave, website].
A son of Clarissa and Samuel Hill named George Littlewood Hill recorded his mother's birth date as Jun 18, 1763 [wikitree]. Her tombstone in Smithfield, Henry Co. KY has her age at date of death in 1747 as 80 (born 1766/7) [find-a-grave, website].
The identity of William's wife is unclear. Some sources say Mary Carter, some say Mary Smith. Between 1733 and 1778 over two dozen white women had bastard children and were fined or punished (whipped) in Caroline Co. VA. A Mary Smith was among those punished in 1769, which would be a few years after William's last known child was born [Campbell, p. 427-8].
William's father may be John Holloway who in his will left to the William Holloway "of Carolina County" who, with his wife Mary (Smith, daughter of Peter Smith), deeded property in Spotsylvania Co. VA on Aug 5, 1755. According to John's will, William and son Samuel were both to inherit "the land where I live" [Will of John Holloway, 1757]. "John Holloway, Jr." was the sole executor of the estate of John Holloway in Caroline Co. VA. When he (Jr.) died in 1769, "Elizabeth Holloway" [his widow] was made executrix [Campbell, pp. 483, 479].
Spotsylvania Co. Virginia is on the western border of Caroline Co. and was formed in 1721 from parts of Essex, King and Queen, and King William counties (see present day map for location). It was named after VA Lt. Gov. Alexander Spotswood.
If William's wife was Mary Smith, daughter of Peter Smith, but there were no records of a Peter Smith in Caroline Co. VA. If his wife was Mary Carter, a brother of hers may have fought with William's brother Nathaniel in the French and Indian War (1754-1763) [Campbell, p. 483].
A daughter of Peter Smith (born 1660 Va. and died Dec 31, 1704 in Northhampton Co. VA), Sarah Smith (1698-1772), married Francis Armistead. They had a daughter Mary Elizabeth Armistead, born Jul 12, 1716, who married Capt. John Carter about 1737. Possible wife Mary Smith could have been a granddaughter of Peter Smith [geneanet.com, website].
Brother John's will, written in Essex Co., was presented for probate in Caroline Co. VA. "Elizabeth Holloway and John Holloway, executors of the will of John Holloway, present his will 12 April 1764" and were the executors on Sep 15, 1764 when a Robert Gilchrist claimed money with costs from the estate [Dorman, Caroline County VA Order Book, 1764-1765, v. 1, pp. 80, 297]. In 1764, "John Holloway, Jr." was the sole executor of the estate of John Holloway in Caroline Co. VA. When he (Jr.) died in 1769, "Elizabeth Holloway" [his widow] was made executrix [Campbell, pp. 483, 479].
On Oct 5, 1794 daughter Frances married William Hudson (1745-1797) in Caroline Co. VA [Dodd, Va. Compiled Marriages 1660-1800].
A daughter of son John, Frances C. "Fannie" Holloway Talbott (1793-1858), married a son of son George, John Alexander Holloway, on Aug 5, 1819 in Winchester, Clark Co. KY. and they had 11 children. So they were cousins and William was their sole grandfather [Dr. Robert Holloway, family history].
On Dec 24, 1849 a son of John A., Edward M. (1826-1907) married Caroline Lee in Monroe Co. MO [Find-a-grave, memorial of Edward M. Holloway, #57472710].
Sources:
Campbell, T.E., Colonial Caroline, A History of Caroline County, Virginia, The Dietz Press, Richmond VA, 3rd ed., 1989, pp. 53-54, 305, 318, 380-1, 427-8, 430, 442, 473, 479.
Caroline Co. Deed Book, Part II, p.135.
Dodd, Jordan, Va. Compiled Marriages 1660-1800, ancestry.com.
Dorman, Caroline County VA Order Book, 1764-1765, v. 1, pp. 65, 80, 297.
Find-a-grave, memorial of Edward M. Holloway [grandson], #57472710, identifying immigrant ancestors, unknown contributors.
Holloway, Dr. Robert, Rochester NY, emails Jan 2026, re: shared DNA ancestor.
Louisa Co. VA Genealogy, "Caroline Co. Creeks and Rivers", map drawn 1751 by Joshua Fry and Peter Jefferson, website.
Olson, Marie K., compiler, "William Holloway", Charleston SC, Apr 9, 1988; ref to Moss, Bobby Gilmer, The Patriots at the Cowpens, Greenville SC, A Press, p.117.
"Virginia Troops in French and Indian Wars", Virginia Hist. Mag., v.1, 1894, p. 389.
Prince George Co., Virginia Deeds 1713-28, page 292.
Mormon records, "John Holloway", AFN:MGP0-F1, LDS CD-ROM, Jun 23, 1994, Family History Library, Salt Lake City UT.
Will of John Holloway, dated Dec 13, 1757, probated Jul 24, 1758, Will Book 1, Cumberland County VA, p. 153.
Will of John Holloway Jr., Apr 21, 1769, Caroline Co Wills 1742, 1762-1830, reel 7, p. 13.