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This examination of the various families and their inter-connectivity will be in at least six distinct areas, which are:

01.  Richard Woolsey and Sarah Fowler Family and notes;
02.  John Woolsey and Mary Sammis Family and notes;
03.  Conjecture that the widower Richard Woolsey actually married the widow Mary Sammis;
04.  Sampson Woolsey was named as the son of one Richard Woolsey and Mary Woolsey;
05.  Denton Woolsey and Leah (______) Family
06.  Sampson Woolsey and Mary Gillette Woolsey Family and descendants.
01.  The area of Richard Woolsey and Sarah Fowler has been a difficult research for many years and it is hoped that the following may shed a little light on the problems encountered here.

From the “Cemetery Records of the Town of Bedford 1681-1975” [FHL# 974.7277/B1 N2b], volume 8, page 393:  “Richard Woolsey [1697-1777] son of Thomas Woolsey.”  BU 7 [Bedford Union Cemetery]

HIST: Woolsey, Cyprian Meech.  HISTORY OF THE TOWN OF MARLBOROUGH, ULSTER, NEW YORK, from its earliest discovery.  Albany.  J. B. Lyon Co., 1908.  471 p. facsims. maps, ports.  photocopy of original, 1992.  includes index.  p. 305.  "The Marlborough Presbyterian churchyard is almost as old as the first two spoken of; the first interment there was in Mar, 1764 -  a child of James Merritt; and the following are some of the oldest graves I find there:  Richard Woolsey, born 1697, died 1777, [wrote his will 1779] aged 80 years.  Sarah Fowler, wife of Richard Woolsey, died 1770.   [Will probated 12 Dec 1782, see below -  " . . .Sarah his well beloved wife" is mentioned in his will  www.]

Woolsey, C. Meech [Attorney & historian of Ulster Co, NY - op. cit.] “History of the Town of Marlborough …” “First baptisms, marriages and deaths in Ulster County: 
page 305:  Richard Woolsey, b 1697, d 1777, aged 80 years  Sarah Fowler, wife of Richard Woolsey, died 1770.


There is a gravestone marker at  Bedford Union Cemetery for Richard Woolsey, with this information but the stone is a much later stone.

From the above dates for Richard and Sarah, all the early researchers of the Woolsey Family ascribed to Richard Woolsey and Sarah Fowler those birth and death dates, and everyone seemed to be satisfied with the results.  However when we dig a little deeper we run across some disturbing information.  For example,

Richard Woolsey (1697 -) wrote his will on 21 Apr 1779, two years after his supposed death in 1777, so he evidently died after 1779.  His will was proved  12 Dec 1782, so he died sometime prior to that date.  So we can now say that Richard Woolsey (1697 - 1779/1782) is coming closer to his actual death.

Sarah  Fowler, wife of Richard Woolsey, was said, as above, to have died in 1770, but Richard Woolsey, in his will written 21 Apr 1779 says “I give to my well beloved wife Sarah ….”.  She was not mentioned when the will was proved on 12 Dec 1782.  So now we can say that Sarah Woolsey (1698 - 1779/1782) is close for her death date.

[An aside:  ]  One may wonder why Richard Woolsey (1697-1779/1782) said, in his will, that he was of “Bedford, Westchester, New York”?

The following deed, sent by Jeff Miller, started us off on this fantastic search. 
Dutchess County, New York DEEDS  FHL# 565013.  Vol. 7 page 517.
 
"This Indenture made the fifth day of March and in the year of our Lord Christ one thousand seven hundred and eighty tow [sic] between Richard Woolsey of Amenia Presentes  [Precinct] in Dutchess County and the Provence of New York and Mary his wife of the one part and Samson Woolsey their Son of the Same Place of the other part witnesseth that that the said Richard Woolsey by and with the consent and advise adn the good liking of Mary his wife and by these Presents for an Consideration of love and affectoin hath given...."
"Be it remembered that on the 26th day of April in the year one thousand seven hundred and eighty four Persoannly appeared...Mary Woolsey one of the signors of the within instrument and acknowledged the same to be her free Act and Deed...and further that she saw Richard Woolsey the other sealer...seal the same at the same time....

So, if the above Richard (now with wife Mary and a “son” Sampson) is our Richard (1697 - 1779/1782) we can now narrow down his death date even more.  Sometime between 5 Mar 1782 and 12 Dec 1782 our Richard Woolsey passed away.

Richard Woolsey (1697 - bet 5 Mar & 12 Dec 1782)
Sarah Fowler (1698 - bef 5 Mar 1782), his wife



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Carolyn Woolsey Wilkerson

DUTCHESS COUNTY, NEW YORK WOOLSEYS