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This is very interesting. Do you have dates on this Benjamin?
I have the impression that some of the apparent migration of the Phipps families in VA and NC may be simply due to the ever-changing county boundaries. Evidently if you'd sit still long enough, you'd end up in two or three different counties. There's an animated file at www.familyhistory101.com/maps/nc_cf.html that will graphically show the extreme changes in county names and boundaries in NC over the years.
My Y-DNA results seem to suggest a probable connection from the Ashe Co., NC Phippses to the Quaker PA Phippses. They were essentially kicked out of England because of their religious beliefs, and my suspicion is that they were then kicked out of the Quaker church for various "sins" such as marrying non-Quaker. That might explain why they seem to have dropped out of the sky and landed in VA/NC.
I had also suspected a Melungeon element in the family, which, if it was true, might explain why tracing the family back has been problematic. The DNA, however, clearly indicates British Isles roots. My direct ancestor Samuel Phipps (1762-1854), on the other hand, married Betty Reeves (1762-1845), and she is believed to have been Melungeon or to have had Melungeon roots. (See Robyn Vaughan Kennedy, The Melungeons: The Resurrection of a Proud People, pp. 60-61 - you can preview it in Google Books.)
Here are items pertaining to individuals named Benjamin in the area, perhaps some of which connect to the individual you mentioned:
Benjamin Phipps, born 1732, died 3 May 1838, buried Benjamin Phipps Family Cemetery, Grayson Co., VA
Benjamin Phipps, 13 Apr 1750, 400 acres on North River, Hampshire Co., WV surveyed for him by George Washington
Benjamin Phipps, born 1761, died 3 May 1838, Phipps Cemetery, Grayson Co., VA
Benjamin Phipps, 28 Feb 1786, his land mentioned in connection with appointment of road overseers, Montgomery Co., VA
Benjamin Phipps, born about 1788 VA, 1860 census, Grayson Co., VA
Benjamin Phipps, born about 1794 NC, 1860 census, Alleghany Co., NC
Benjamin Phipps, 20 Nov 1794, Grayson Co., VA, his land mentioned in deed involving Joshua Cox
Benjamin Phipps, born about 1795, 1850 census, Ashe Co., NC
Benjamin Phipps, born 10 Apr 1795, died 13 Dec 1880, buried Salem Cemetery, Morgan Co., KY
Benjamin Phipps, 1796, Grayson Co., VA tax list, 104 acres
Benjamin Phipps, 1799, Grayson Co., VA tax list, 104 acres
Benjamin Phipps, 30 Sep 1800, marriage or bond date to Rachel Simmons, Guilford Co., NC
Benjamin Fipps, 1800 census, Guilford Co., NC (no adult male listed in household, so likely he died not too long before then)
Benjamin Phipps, Oct 1810, Grayson Co., VA, did not show up as grand juror
Benjamin Phipps, Jan 1811, Grayson Co., VA, appointed to road committee
Benjamin Phipps, Aug 1811, Grayson Co., VA, bond in George Reeves estate
Benjamin Phipps, Oct 1811, Grayson Co., VA, on grand jury
Benjamin Phipps, May 1812, Grayson Co., VA, appointed road committee overseer
Benjamin Phipps, 1813, Grayson Co., VA, personal property tax list
Benjamin Phipps, 1818, Grayson Co., VA, Superior Court juror
Benjamin Phipps, 1832, Grayson Co., VA, mentioned in Rev. War pension applications of Isaiah (Isiah) Austin and James Cox; testified in behalf of James Cox and John Fielder
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