Some DNA databases including the GREGORY surname:

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Joseph Gregory Senior died c1842 Rutherford Co., TN, having moved there from Lunenburg Co., VA at an advanced age.
Joseph Gregory Senior born c1742; where unknown
Joseph Gregory Senior married before/by 1765 (John, one of eldest children, b. 13 Dec 1765)
Joseph Gregory Senior married 3 or 4 times, only last 2 known.  Mother(s) of his children unknown.
Joseph Gregory Senior died between 1840 & 1850 Census in Rutherford Co., TN where he moved in 1837/1838 at an advanced age
Parents: Father: unknown; Mother: was this Joseph Gregory Senior same as the son Joseph Gregory named in the will of Milderidge Gregory-Vaughan?
Will: None  (see list of children of Joseph Gregory Senior in lieu of will)

Joseph Gregory apparently lost his wife about 1805 or 1806

Joseph remarried in Charlotte Co., Va., 8 Jan. 1807, Mary Magdalene Herndon, widow, (note: nee Roberts) and sold his land in Mecklenburg Co.

Joseph Gregory Senior 1810 Census Charlotte Co., VA
1 Males (over 45)
1 Ma;e 26-45
1 Male 16-26

1 Female (over 45)
1 Female 26-45
1 Female (under 10)

That this move did occur is evident by four related (but insignificant looking) papers in the Josephus Gregory Collection, which papers also attest to the facts:

1)Joseph Gregory was the name of the grandfather of Josephus Gregory (son of John) of Lunenburg Co., VA.

2)That Joseph Gregory left the home of his son John Gregory just two days prior to the 11 Dec. 1828 marriage date of Joseph Gregory to Alice Davis, Lunenburg Co., Va.

The 1st paper was signed by Thomas N. Gregory, son of John:
On demand with interest from date John Gregory (of Lunenburg County Va.) promise to pay or cause to be paid unto Joseph Gregory the just and full sum of Three Hundred and Eleven Dollars Thirty Seven Cents lawfull money of Va. as witness my hand and seal this 18th of May 1827 Taken in by Thos. N. Gregory in full.
Test
Thos. N. Gregory

On the reverse side of the 1st paper are four receipts (signed twice by Joseph Gregory):
6 May 1829, $36.65 in part of the written bond; 12 Jan. 1830, $180 in part of the written bond; 25 Oct. 1831, received $50 in part of the written bond; 13 Feb. 1829 recd. $11.25 of the written bond. These figures appear on the 3rd paper.

The 2nd paper was signed by Josephus Gregory, son of John:

Richard L. Smithson, Father's account about Grandfather's horse says he came here 15 April 1826 and left here 9th December 1828. (Note the marriage date compared with this date./jgs)

The 3rd paper is an accounting signed by Rich. L. Smithson and John Knight, 18 May 1827, stating "Agreeable to the papers exhibited to us it appears that there is a balance of 71.04 due on the bond of 311.37 executed the 18th May 1827 from John to Joseph Gregory."

The paper, headed "Bond due from John Gregory to Joseph Gregory," begins with "Principal due 18th May 1827 is $311.37." Deducted are the several payments; also, amounts for keeping the horse the winter of 1826 and 1827, and for 1827 and 1828. Added to each subtotal is interest.

Joseph Gregory Sr. was getting his affairs in order, not because of his age (about 86), but because he was about to remarry to Alice Davis.

Joseph Gregory 1830 Census Lunenburg Co., VA
1 Male 80-90
1 Male 5-10 (who?)

1 Female 50-60

Papers showing Joseph Gregory Senior went to Tennessee in his advanced years:

20 May 1837 Joseph Gregory Senior's son Thomas Gregory wrote from Maury Co, TN to his nephew Josephus Gregory (son of John) of Lunenburg Co., VA  "I have been trying to get some person that I could depend on to go in after Father as it is out of my power to come myself with any degree of convenience....If you will take the trouble to get some safe hand to come out with him I will pay the expense of the trip together with the expense you may be at in fixing him of.  I think that had better have a carriole & a good gentle horse.  Bring nothing but the wearing clothes & bedding & try to prevail on him to [leave] his old Negroes except Bachley?" [Gregory Family Correspondence]  (John Gregory, the last son of Joseph living in VA, had died in Lunenburg Co., VA Sept 1836.)

March 1838 Josephus (grandson of Joseph) wrote that friends in Tenn. said "Grandfather and his wife were well and well pleased and the connections generally in Tensee were also well."

Joseph's son Thomas d. 22 Nov 1839.  It is not known if Joseph 1st went to Maury Co., TN to be with Thomas.  By 1840 Census, Joseph was listed next to son Edward in Rutherford Co., TN

J. Sol Gregory (son of Thomas) in a 1906 interview in Columbia, TN said that his grandfather Joseph Gregory died in 1844 or 1845 at his son Edward's [Rutherford Co., TN], lacking a few months of being 100. .[ Frank H. Smith, ”History of Maury County, Tennessee" (In an interview in 1906)]