Richard Woolsey 1747-1825

Descendants of Richard Woolsey 1747 - 1825

RICHARD WOOLSEY (THOMAS6 , RICHARD5 , THOMAS4 , GEORGE "JORIS"3 , GEORGE SR2 , WILLIAM WOLSEY1) was born 1747 in NY - Bedford, Westchester, and died 1825 in KY - Somerset, Pulaski. He married NANCY ANN PLUMSTEAD Abt. 1768 in NY - Ulster County, daughter of JOSEPH PLUMSTEAD and SARAH. She was born 1755 in NY - Newtown, Queens, and died 1823 in KY - Jessamine County.

Family of George Wood Woolsey & Sarah Nelson
by Hester Woolsey Brewer
It is supposed that Richard Woolsey and his wife Nancy Plumstead accompanied Rev. Thomas Woolsey on his trip to Washington County, Va. At least he was there most of the time, as attested by official county and military records. He was one of the witnesses to his father's will. He was appointed Constable in the Captains Company in this County March 21, 1783, and served in the Revolutionary War from Washington County. He served in Captain William Campbell's Company, Fincastle Battalion, 1774, Robert Doak's Company of Militia, 1774, and Captain Russell's Company in 1783. He was among those who fought in the battle of King's Mountain, Oct. 1780, when the fight raged between Campbell and the British under Ferguson. He was with Captain Campbell's Company in the expedition to Point Pleasant in 1774. Other members of the family to enlist in the Revolutionary War from Washington County, Va., were Zephaniah, William and Thomas, Jr. Thomas Woolsey, Revolutionary soldier, later resided in Caldwell and Christian Counties in Kentucky. John Woolsey, a relative of Rev. Thomas, is listed in the Virginia Militia of Brunswick County, Va., in 1758, under Capt. Edward Goodrich.

Washington County, VA Survey records abstracts 1781-1797
Part 3 of 5 (pages 201-300)
Submitted to the USGenWeb archives and copyrighted by
Rhonda Robertson [email protected]

Page 161 - James Wheeler...290 ac...CommissionersCertificate...on the waters of the south fork of Holstein...Beginning corner to Henry Bowens land...on Bowens road by a dry branch...on Moses Ashbrooks land...with Joseph Coles land...corner on John Pattersons land...June 6, 1782 - James Wheeler, assignee of Richard Woolsey...400 ac...on the waters of the south fork of Holstein River, includes improvements, actual settlement made in
1774...August 30, 1781)

Page 284 - Thomas Woolsey, Richard Woolsey & John Perce - 300 ac - Treasury Warrant - on the South Fork of Holstein River - adjoining the land Thomas lives on - corner between John Perce and Woolsey - with James Wheeler's land - with Joseph Cole - August 18, 1785

After the death of his father Richard as head of the family went pioneering as his forebears had done, and it is supposed that his mother made the journey with him, as she would hardly remain behind in Virginia. It was twenty years after Daniel Boone had blazed the trail through the Cumberland Gap that Richard followed him into the wilderness of Kentucky. The state had been separated from Virginia but a short while and about the time Richard traveled through the Gap other white men were filing into Kentucky by boat or raft down the Ohio River from Fort Pitt. By 1749 Virginians had been showing a great interest in the country beyond the mountains and as a result, two land companies were organized and bought up vast tracts of land. But it was not until a half century later that emigration was stimulated to a nocticeable degree. Those who now came into this district to establish homes, excluding negro slaves, were 95% pure English, Scotch, or Scotch-Irish descent.

Leaving his home near the Holston, and on his way to Kentucky, Richard must have traversed a route quite near the location of a cabin built later by Jeremiah Woolsey, who after building his cabin remained only a short time in
this vicinity and in 1807 removed to either Indiana or Illinois, leaving the land to his descendants, some of whom still retain title to it. I am unfamiliar with the relationship of Jermeiah to Rev. Thomas Woolsey, but doubtless he was a grandson.

On the fist lap of his journey Richard could not have been doubtful of his undertaking if he wished to establish his home in a new and lovely country. The beauty of the Cumberland Gap at that time and even today is difficult to surpass. Now its solemnity is disturbed by the hum of motor cars over the asphalt pavements as numerous tourists crisscross between Virginia and Kentucky beneath its towering cliffs, but in the day of Richard's travels he, under the watchful picket, must have slept in peace as he camped with is family surrounded by his household effects, horses, cattle, and perhaps a few slaves and a dog or two.

Though the militia, situated in the widerness posts, relieved to some extent the danger of travelers being attacked by savage tribes, vigilance and scouting were necessary every foot of the way.

The Cumberland Gap, when Richard first traveled it, was a path about ten feet wide with the towering mountain stabbing the sky two hundred feet to the right and opposite, two hundred feet below, the foaming waters of the Cumberland River gnawed the stone at the base of the steep declivity.

All streams encountered had to be forded, which with stock, farming and household effects, women and children, was no light matter for consideration. After filing through the Gap and escaping the horrors of the scalping-knife or arrows of the Indian, he had then to conquer the dense cane brake, where the cane grew to the height of eight to ten feet and served as a breastwork for roaming animals and savages of the wild.

But evidently Richard was spared the horrors of meeting these foes on his pilgrimage and in due time filed father toward the northwest through what is now known as Burnside, named for our General Burnside of the Civil War whose home was in this vicinity.

About ten miles north of Burnside is now located the little city of Somerset and it was in this locality that Richard halted his caravan. Here also we find precipitous slopes and sleepy valleys and here Richard's family found the same happiness which was theirs in the Virginia home beyond the rugged cliffs of the Cumberland Gap. The streams are bound by slopes up which tall slim trees climb and from the top of the ridge receive the benediction of the morning sun, while about lie monarchs of the past laid low or dismembered by fierce combat with the elements.

The site of the new home was later included in the County of Pulaski, which was formed in the year 1798, and it was in this territory that the descendants of Richard Woolsey and his wife Nancy Plumstead made their home for nearly three-quarters of a century.

They resided on and cultivated their land, but what their crops consisted of is only surmised, though in my father's youth tobacco was one of the principal crops cultivated. In 1842 raw silk was produced in this region and two years later the first silk factory in Kentucky was located at Newport, but this venture evidently was not successful and I believe most Kentuckians in this vicinity farmed their lands.

I have no way of knowing how many members of Richard's family accompanied him on this journey into Kentucky, but on the records of Pulaski County I found land recorded in the names of Geroge Woolsey and wife Jane Hall,
grandparents of my father George Wood Woolsey, in 1827 on Clifty Creek; Wesley Woolsey on Big South Fork of Cumberland River, 1824; and _____ Woolsey on Big South Fork of Cumberland, 1837.

1810: PULASKI CO., KY.
Wolsey, Nathaniel
Wolsey, Richard

1820: PULASKI CO., KY.
Wolsey, GEORGE
Wolsey, Richard
Wolsey, William

1830: PULASKI CO., KY.
Woolsey, Jane
Woolsey, Sarah
Woolsey, Richard
Woolsey, William

1840: PULASKI CO., KY.
Woolsey, Sarah
Woolsey, William

1998 March 22 from Wilford W Whitaker:
Richard WOOLSEY, a son of the Rev. Thomas WOOLSEY, a Baptist preacher in New York and Washington County, VA, and of Thomas' wife Sarah (Sarah PIERCE?), is said to have married Nancy PLUMBSTEAD/PLUMSTEAD of Ulster and Orange County, New York. Is she the daughter of Francis PLUMSTEAD and a sister of Nathaniel PLUMSTEAD of Ulster and Orange Counties, NY? Richard WOOLSEY was in the Revolutionary War, enlisting at New Windsor "on the North river on Hudson's" in 1775/1776. He was at the battle of Long Island, White Plains & "other militia battles" but enlisted in the Continental Line under Capt. John MONTGOMERY and was in Gen. Wooster's Brigade. Richard and Nancy came to Washington County, VA where the Rev. Thomas WOOLSEY was "on the south fork of the Holstein" and then Richard and Nancy came to Pulaski and Jessamine counties, Kentucky. Nancy was 68 years old in 1823. Does any one have documentation on these families? I can document all of above except marriage of Richard WOOLSEY and Nancy PLUMBSTEAD. Thank you.

1782 Personal Property Tax List
Col. Arthur Campbell's Precinct
[This section of this tax list is faded, and very difficult to read.]

I, Wilford W. Whitaker have been studying the 1782 Tax List of Washington County, Virginia, and have wondered for sometime why the Woolseys do not appear on this list. As I studied the Land and Survey Records and learned who were neighbors of the Woolseys, I have come to the conclusion that they are on this Tax List, but wrongly identified. They should have appeared as living close to Jonathan Dean but they do not. However, there are the following, which should become apparent, in just a little while.
Listed in the records are
Richard Woling
Thomas Woling
After an exhaustive search, WOLING is not a name that is found in Washington County, Virginia. At this time, I believe that the above Richard & Thomas WOLING is a misreading of Richard [md Nancy Plumbstead.]& Thomas WOOLSEY, the father. - Wilford

In questioning Wilford Whitaker in regards to the burial place of Richard since I could not find a Jessamine County, KY. He replied: "Jessamine County, KY., was formed in 1798 from Fayette County, KY. I have found some records in this county, mainly Richard Woolsey (who married Nancy Plumstead), his Rev. war pension application and the only reference I have found to my great-grandfather Joseph Woolsey who married Abigail Schaeffer.

2010 September 22 FROM Wilford Whitaker I discovered a Richard Woolsey who lived on the "south side" of the Nolichucky River, but several miles distant from Zephaniah and Sarah Woolsey. Woolsey, a brother of your John Woolsey, who had "settled on the south side of the Nolichucky".

It came as a great surprise to me that this Richard Woolsey, who sold 300 acres of land on the Nolichucky in 1800 was, in fact, my direct ancestor, Richard Woolsey, the Revolutionary War Veteran, and his wife Nancy Plumstead. Richard Woolsey is the son of the Baptist Preacher Rev. Thomas Woolsey of NY and Washington Co, VA and his wife Elizabeth Waters (some say Sarah Pierce, but I believe this Sarah Pierce was a second wife.)

My Richard Woolsey led a nomadic, exciting life. Born in New York State, he probably moved with his father to Washington County, Virginia, about 1771, then my Richard was a soldier in Lord Dunmore's war against the Indians on the Virginia frontier. Richard then appears back in New York State to serve under George Washington at the Battle of White Plains, Kings Bridge and possibly Boston. He then appears in Virginia again living close to his father and then, evidently receiving a land grant of 300 acres (which I have not found) he appears in Greene Co, TN "on the Nolichucky river", which he then sold about 1800 and where his son Jacob C. Woolsey marries Elizabeth Weger in 1801 and then Richard returns to Virginia, then to Jessamine County, Kentucky, where he applies for a Rev. War Pension, and then dies there.

Religious Assoc: Quaker

  1. NATHANIEL WOOLSEY, b. 1769, NY - Ulster County; d. Bef. 1850, IL - Franklin County; m. (1) REBECCA GLENN, Abt. 1799, KY; b. Aft. 1770, IRE; d. Abt. 1806; m. (2) REBECCA RICE, September 29, 1807, KY - Madison County; b. Abt. 1791; m. (3) SUSANNAH, Abt. 1813, KY; b. 1786, KY; d. Aft. 1850, IL - Franklin County.

  2. JOSEPH WOOLSEY, b. 1771, NY - Ulster County; d. Bet. 1839 - 1840, IL - Vandelia, Fayette; m. (1) MARY "POLLY" CAZAIRE, Abt. 1796; b. Abt. 1776; d. 1802, KY - Lincoln County; m. (2) ABIGAIL SCHAEFFER, Abt. 1804, KY - Lincoln County; b. September 13, 1786, MD; d. September 02, 1848, WY - Utah Territory.

  3. RUTH WOOLSEY, b. 1777, VA - Fincastle County; d. Bef. 1841, KY.
  4. THOMAS WOOLSEY, b. 1777, NY - Ulster County; d. Bef. 1819, KY - Sinking Creek; m. (1) MAHALA/MARGERY BURNS, Abt. 1796, VA; b. 1778; m. (2) SALLY "POLLY" BARNES, April 04, 1812, KY - Pulaski County.

  5. JACOB C WOOLSEY, b. August 22, 1782, VA - Washington County; d. Bet. 1856 - 1860, UT; m. (1) ELIZABETH WEGER, July 30, 1800, TN - Greene County; b. 1780, IL; m. (2) ELIZA TRICK, 1838, MO - St Genevieve; b. 1810, IL.

  6. GEORGE WASHINGTON WOOLSEY, b. 1785, VA - Washington County; m. ELIZABETH GOFORTH, June 16, 1819, KY - Jessamine County.

  7. SARAH WOOLSEY, b. 1790, VA - Washington County; d. 1840, KY - Pulasky County; m. EBENEZER VAUGHN, February 03, 1819, KY - Pulaski County.

    Fayette County, Kentucky, Marriage Records, compiled by Michael Cook et al, Cook Publishing Co., Evansville, Indiana. 1985 in 3 volumes. 3:145.
    Sarah Woolsey married 3 Feb 1819 to Ebenezer Vaughn, with Karrick Kinder, Surety. Richard Woolsey and Mary gave consent for daughter."

  8. NANCY WOOLSEY, b. 1792; m. MATTHEW HALL, October 12, 1812, Pulaski Co, Kentucky.

  9. RICHARD JR WOOLSEY, b. 1795, KY - Pulaski County; m. ELIZABETH MAYNARD, November 30, 1815, KY - Jessamine County.

  10. GEORGE WOOLSEY, b. 1796, KY - Boyle County; d. July 10, 1830, KY - Montgomery County; m. JANE HALL, September 03, 1816, KY - Pulaski County; b. 1799, SC; d. Aft. 1860, KY - Pulaski County.

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