I think this John Day was born in England and came to America for business and to get land he died in England in 1757. I don't believe he was son of John and Elizabeth Mason Day. Hoyt Day 
Some sources shown this John to be the son of a "John Day who came to Virginia in 1620 and worked as a mastersmith and carpenter having several sons, one being John Day II who almost everyone has his wife as Mary Bennett daughter of Edward Bennett merchant and land owner who is probably a very wealthy person. The "Upper Class" back then as today didn't approve of their children mixing with the "Lower Class". My question is would Mary Bennett "daughter of a wealthy merchant" be allowed to marry John Day "son of a blacksmith"? Hoyt Day 
He married Mary BENNETT b. 1632 Stepney, Middlesex, England d. 1690 Rappahannock Co., Virginia. 
Child Mary was born in 1644, at which time Mary Bennett would have been 12. This suggests some dates will need to be adjusted, to either make the mother older or the daughter younger!
John Day married Mary Bennett, daughter of Edward and Mary (Bourne) Bennett. In 1622 Edward Bennett established the first permanent plantation in the new colony, called Bennett’s Welcome, of 1500 acres that was granted to him in 1621.
John’s wife, Mary Bennett, was born about 1623. She was born in Wiveliscombe, Somerset, England. . However, other material reports her birth in Stepney, Middlesex, England 
Property in England
John Day inherited property in England as a result of his wife's dowry & thus his will was probated in Middlesex, England. 
Several trees have Mary Bennett-Day-Bland-Cropley died about 1690 in Rappahannock co, Virginia but I haven't seen a record of this.
To all & c whoever & c Now Know ye that I the said Richard Bennett Esquire give and grant unto John Day four hundred acres of Land, situated in the County of Gloucester, Upon on the South East Side of Poropotank Creeke in the Woods bounding as ffolloweth Vizt upon the head of Mattapony Creeke and upon the North East of a swamp which devideth this Land and the Land of Isaak Richeson and Extending along a branch of the said swamp which devideth this Land and the Land of Willm. Kinsey North East by North two hundred pole to the South west side of a white Marsh into the woods South East and by East three hundred and twenty pole South west and by South upon the Land of Isaac Richeson North west and by west upon the Land of William Baysey, the said Land being due unto the said John Day by and for the transportation of Eight persons into this Colony &c. To have and to hold &c. Yielding and paying &c. which payment is to be made seven yeares after the first grant or seating thereof &c! Dated the 19th of October 1653 ~
Mary Hockett } Francis Jacobs } Judith Laton
Elizabeth Hockett } Thomas Lake } Ann ??old
Mary Glover } Thomas Clarye }
1657 Mary named as wife in John Day's will
John Day of Fulham, co. Middlesex, Gent., (Calendar of Wills, court of Hustings, London, p. 771) by will dated September 15,1657 and proved the following January, left pecuniary bequests to children, John, James, Elizabeth, Anne, and to his wife Mary all lands and tenements held of the lord of the manor of Stepney, Middlesex, and elsewhere, for her to sell and dispose of as she should please for the better maintenance of herself and her children. 
Death and Will
John Day died 15 Sept 1657 in Fulham, Middlesex County, England. He had become ill & went to England for treatment & died there. 
Day (John), of Fulham, co. Middlesex, gentleman.--Pecuniary bequests to
John and James his sons,
Elizabeth and Anne his daughters.
To Mary his wife all his lands and tenements held of the lord of the manor of Stepney, alias Stebenheath, co. Middlesex, and elsewhere, for her to sell and dispose of the same as she shall please for the better maintenance of herself and children.
Mary DAY b. 1644 VA,  I have found marriage records of Mary Day to Thomas Bland 1758, then Mary Bland to Luke Cropley 1668 both in England. It is my belief that all her children were born in England and also believe James Day was the only one who went to America. 
Anne Day b. 1645-1658 VA mar Charles CHAPMAN b. 1640-1655, #Anne Bennett Day, b. 1656 in London, England, d. 1736 in England. She married Charles Chapman 1676 in London, England. I'm not sure that Charles Chapman and wife Ann Day came to America, I can't find their passage, nor can I find Charles Molloy and wife Elizabeth Day. 
Elizabeth DAY b. 1645-1658 VA mar Thomas SWANN b. 1640-1655. #Elizabeth Day, born 1651 in England. She married Charles Molloy 1670 in Hertford, England. 
James Day, Sr. b. abt 1645-1658 VA mar Mary THOMPSON b. 1647-1661 VA. # James Day Capt., b. abt 1657 in England, d. Dec 1700 in Isle of Wight, Virginia, USA. He came to America and married Mary Thompson and died there in 1700 leaving 3 sons and a daughter, his wife married John Johnson and then Rueben Gladhill. 
John Day, born 1653 in Fulham, Middlesex, England. I haven't found what happened to son John Day. 
Descendants of John Day and Mary Bennett
Children of James Day and Mary Thompson
Thomas DAY b. 1655-1679 VA mar Jane BRIGGS b. 1657-1681,
James DAY, Jr. b. 1655-1679 VA mar Juliana NORSWORTHY b. 1657-1651
John & Betty had David DAY b. 1743-1770 VA mar Priscilla Sugars BLOUNT.
David & Priscilla had 2 sons, Thomas Ridley DAY b. 1791 VA mar Edith BALLARD.
Thomas & Edith had a daughter, Lydia DAY b. 1818 VA mar William Walter Eley, Sr. 
William Henry DAY, son of David and Priscilla, b. 1801 VA mar Amanda M. F. CHAMBLIS.
William Henry & Amanda had 3 sons: Charles Fenton DAY b. 1848 mar Virginia E. JORDAN-had dau Lucy DAY b. 1874; William Henry DAY, Jr. b. 1850 VA; & Henry Mason DAY, Sr. b. 1851 VA mar Emily GARNETT-had 4 known children:Henry Mason DAY, Jr. b. 1886 VA; Georgia Wayne (female) DAY b. abt 1888 VA; Emily Sutton DAY b. abt 1890 VA; & Garnett DAY b. abt 1892]), 
Line of Descent from Jame Day jr and Juliana Norsworthy
Elizabeth DAY b. abt 1657 VA mar Nathaniel RIDLEY-they had 6
children. Elizabeth had a brother William DAY b. 1655-1679 VA.
Line of Desecent from John Day of Hogg Island
John DAY b. abt 1655 Hogg Island, Surry, VA d. 1725 Princess Anne Co., VA married a miss OLIVER b. abt 1668 VA Their children:
Henry DAY b. 1685 (see below**),
John DAY b. Feb 1690, mar Jane ____. John & Jane had 1 known dau., Judith b. 21 Sep 1729 VA 5c)Edmund DAY b. abt 1715 VA mar Mary YARROW-had 1 known son, John William DAY b. 13 Apr 1735 VA mar a miss MOURNING
Henry DAY b. 1685 VA mar Mary WALTON. Henry & Mary had 7 known children: #Henry DAY b. 1716 Chowan Co., North Carolina mar Mary WOOLSTON--had 2 known children: Henry DAY b. 1743 NC & Mary DAY b. 1745 NC.
John R. DAY b. 6 Sep 1716 Bertie or Chowan Co., NC (*** See below)
Peter DAY, b. abt 1717 Chowan Co., NC d. 1791 Edgefield District, South Carolina mar Charlotte MARTIN.
Elizabeth DAY b. 1717 Chowan Co., NC mar Jeremiah FRAZIER.
Sarah DAY b. abt 1719 Chowan Co., NC mar Charles REGG.
Simon DAY, b Chowan Co., NC.
William I. DAY b. 1724 mar Anne Amelia HARRIS. 
John R. DAY b. 6 Sep 1716 Bertie or Chowan Co., NC d. 1790 Burke Co., NC mar 1753 in a fort in Edgefield District, SC to Lucinda GRIFFIN b. abt 1720 (in the same fort in SC). John R. & Lucinda had 11 children:
William DAY b. Aug 1754 Ft. Moore, 96th District (Edgefield District) SC. d. 12 Mar 1836 Dallas Co., AL mar 1st in 1776 to Frances ____ b. 1748 d. bef 1779. Mar 2nd on 10 Dec 1779 in SC to Rutha PIERCE b. 1760 SC d1840-1850 Dallas Co., AL 
William & Rutha had 11 children.
James DAY b. 1756 Edgefield District, SC d. abt 1819 mar Elizabeth ROEBUCK b. abt 1758.
Benjamin DAY b. 1757-1770
Henry DAY b.1757-1770 had a son Henry DAY who had a dau. Mary DAY who mar Mr. GRUBB.
Peter DAY, b. 1757-1770.
Laban DAY b. 1757-1770.
Edward DAY b. 1757-1770.
Sanders DAY b. 1757-1770.
John Davis DAY b. 1757-1770.
Daniel DAY b. 1757-1770 d. Perry Co., AL mar 19 Jan 1836 in Cahawba, Dallas,
This DAY family went from Virginia to North Carolina to South Carolina (some traveled back to Virginia). The rest went on from South Carolina to a lot of other points, but many went to Dallas Co., Alabama, then to Mississippi, then to Northern Louisiana (where mine ended up in Union, Morehouse Parishes then central Louisiana, Avoyelles & Rapides Parishes). Some DAYs went on to Texas.
The part on William & Rutha is wrong, That is my line and those are not
the right children. Also William was married twice. 
Mary's Subsequent Marriages
Followign John Day's death, Mary married Thomas Bland. After the death of Thomas, Mary Bland married Luke Cropley. Both marriages took place in England. "I can tell James Day was the only one of her children who came to America. I believe she was never in America. Look at the marriage records attached to my tree." 
Untangling two John Days from the same time, same place
There were at least two John Days whose lives overlapped in Virginia's earliest days.
John Day and his wife Elizabeth Mason arrived at Jamestown in 1620. He had been born in Shrewsbury, Shropshire, 12 October 1597, and died 1664 in Gloucester County. They had a son Lewis.
John Day and his wife Mary Bennett are associated with Isle of Wight. He died there April 1, 1701. They had children Elizabeth, John, Anne and James.
The deed which appears above is attributed to John Day of Isle of Wight because the grantor, Richard Bennett, was John's father in law. However, it was later inherited by Lewis, son of John Day of Gloucester. (Hoyt)
It may be that Richard was acting in his official capacity as a high official of Virginia in granting the land, rather than in his personal capacity as father in law of one of the two John Days.
"In the case of John Day some uncertainty arises. Apparently there were two men of this name in the colony, one transported by John Slaughter, and the other not only paying for his own passage, but for that of a servant as well.  A John Day later secured 400 acres in Gloucester county  but whether it was the one who had come as a servant or the one who had entered the colony as a freeman, apparently there is no way of ascertaining. "
↑ Rupert Taylor, Clemson, S. C. "The Parentage of James Day (Died 1700) and wife Mary of Isle of Wight county, Virginia." Genealogies of Virginia Families from Tyler's Quarterly Historical and Genealogical Magazine. Baltimore: Genealogical Publishing Co, 1981; pp 542-545. Reprinted by Clearfield, Baltimore, 2007. Introduction by John Frederick Dorman. Accessed June 20, 2017. jhd
↑ London, England, Baptisms, Marriages and Burials, 1538-1812 for John Day, cited by Hoyt Day.
↑ Addie P. Howell (firstname.lastname@example.org, Day Family Genealogy, 28 May 2003, response to Jeanne Liberato
↑ Virginia Magazine of History and Biography, Vol 5, p. 101, cited by Wertenbaker, p. 80
↑ W. A. Crozier, Virginia County Records, Vol VII, p. 177, cited by Wertenbaker, p. 80
↑ Thomas Jefferson Wertenbaker, The Planters of Colonial Virginia. Princeton University Press, 1922. P. 80
Source: S-1395311598 Repository: #R-2138831855 Title: U.S., Sons of the American Revolution Membership Applications, 1889-1970 Author: Ancestry.com Publication: Online publication - Provo, UT, USA: Ancestry.com Operations, Inc., 2011.Original data - Sons of the American Revolution Membership Applications, 1889-1970. Louisville, Kentucky: National Society of the Sons of the American Revolution. Microfilm, 508 rolls Note: APID: 1,2204::0
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