William was born about 1776, presumably in Halifax, Virginia.
On 16 Apr 1814, William Holloway of Person, North Carolina transfers 25 and one half acres in Halifax, Virginia to Garland White of Halifax, Virginia. [1]. This appears to be the same 25 and one half acres transferred to his father Nathan Holloway from Richard and Nancy Brooks on 7 Apr 1804 [2]. This is notable not only because it indicates that the land was conveyed to William by Nathan, but that William was residing in nearby Person, North Carolina in 1814. His father and some of his brothers are located in Sumner, Tennessee by 1820.
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H > Holloway > William Holloway
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This presents a bit of a continuity challenge because there appears to be a census record for Nathan and Nathan, Jr. in Sumner, Tennessee for 1820.
This is my first deep pass at trying to make sense of Nathan and family, but it seems strange that Nathan would have deeded his land to William and moved to Sumner, Tennessee with some of William's brothers.
Is it possible we're missing a Nathan here that perhaps explains a generation gap? One who died in Halifax, VA but had a son and grandson both named Nathan who are the ones found near brothers in 1820 Sumner, Tennessee?
"United States Census, 1820," database with images, FamilySearch (https://www.familysearch.org/ark:/61903/1:1:XHLT-49S : accessed 26 May 2022), Nathan Holloway, Gallatin, Sumner, Tennessee, United States; citing p. , NARA microfilm publication , (Washington D.C.: National Archives and Records Administration, n.d.), roll ; FHL microfilm .