Settlers By the Long Grey Trail, Some Pioneers to Old Augusta County, Virginia, and Their Descendants, of the Family of Harrison and Allied Lines was written by John Houston Harrison and published in Dayton, Virginia, by Joseph K. Ruebush in 1935. The author was a grandson of John Harrison (1800-1880) and his wife Barbara Catherine Hollingsworth (1817-1890). The following extracts from the book contain all the Hollingsworth information to be found within it.

pages 455-456:

John Harrison married, January 25, 1838, Barbara Katherine Hollingsworth, (1817-1890), the daughter of George Hollingsworth, and wife Nancy.

George Hollingsworth resided in the Lacey Spring neighborhood. The old cemetery in which he was interred, and which probably marks the site of his land, is on a farm to the north of Locust Grove. He came to Rockingham from present Page County (formed form Shenandoah, 1831), and was a descendant of the early Hollingsworth family of Frederick. (See page 134.)

Hollingsworth

Valentine Hollingsworth, Sr., the immigrant, it is related, came to America with William Penn. He was born about 1635, and was living in 1710. By tradition, he married, as his first wife, Catherine, the daughter of Henry Cornish, High Sheriff of London. His wife Ann Calvert died in 1697. In 1682, he patented 986 acres of land in Brandywine Hundred, New Castle County, Delaware, and on this settled. He was a member of the Society of Friends, and filled many important positions in the colony, among them serving in the Assembly, 1683, 1687, and 1695.

One of his sons, who came to America with him, was Thomas, of Rockland Manor, New Castle County, Delaware, who died near what is now Winchester, Virginia, 1732. Thomas married, first, Margaret —. She died in 1686-7. He married second, 1692, Grace Cook. By his first wife he had one son Abraham, and by the second four sons, three of whom lived to be married, viz., Thomas b. 1698, Jacob, b. 1704, and Joseph, b. 1709. Abraham and Joseph settled in Virginia.

Abraham Hollingsworth, the son of Thomas, was born 1st Mo. 19, 1686. He married in 1710, Ann Robinson, who died in 1747. In 1732, he purchased, of Alexander Ross, 582 acres of land near later Winchester, Virginia, on which he resided until his death in 1748 (See page 112.) He had two sons George, b. 1712, and Isaac, b. 1722, d. 1759. George married, 1st, Hannah McKay, 1734, the daughter of Robert McKay, Sr., associate of Joist Hite, and 2nd, Jane —, and in 1762 removed to South Carolina. Among his sons was Robert, b. 1744, d. 1799, who married Hannah Rice about 1769, and resided near Winchester. She died in 1833. Their sons were George, b. 1770, Joseph, b. 1773, Lewis, b. 1775, Robert, Abraham, Isaac, John, James, and Edmund, several of whom removed to Shelby County, Kentucky. George married in Frederick, 1799, Mary Gaunt. Lewis married in Frederick, 1814, Abigail Parkins.

Isaac Hollingsworth, son of Abraham, inherited his father's original 582 acres, a part of which, 'The Homestead,' is still in the possession of his descendants. He married in 1748, Rachel Parkins, b. 1724, d. 1806. In 1757, as a minister of the Quaker sect, he removed to Loudoun county, Virginia. He and wife Rachel had two sons, Abraham, b. 1749, and Jonah, b. 1754, d. 1801, of whom the latter inherited the Winchester homestead. Jonah married, 1778, Hannah Miller of Maryland, b. 1755, d. 1836. A son Samuel, b. 1784, was residing Shenandoah County in 1821. (See, Hollingsworth Genealogical Memoranda, by W. B. Hollingsworth, Baltimore, Md., 1884.)

George Hollingsworth, of Rockingham, (probably grandson of Abraham, brother of Jonah) had children, Barbara Katherine, Mary, Jane, Susan, George, John, b. June 20, 1829, James, and Amanda, b. November 19, 1827. Of these: Barbara married John Harrison above; Mary married William Bowyers, and had Joseph, Daniel, George, David, John Newton, Houston, William, Luther, Edward, Dorcas, and Maggie; Jane married Isaac Graves, of Frederick County; Susan (d. about 1856, aged 33 ?) married Philip Webster, (d. 1904 c. aged 67), of Page County, and removed with him to Virgo County¹⁾, Indiana, and had: James Ira, John William, Amanda Jane, b. July 26, 1849), Barbara Ann, b. 1851, and Mary Elizabeth; George moved to Virgo County, Indiana, married Eliza Evans, moved to Kansas, and then to Arkansas; John died in Rockingham, Dec. 20, 1902; James married Catherine Dovel, and moved to Virgo County, Indiana; Amanda died in Rockingham, Dec. 16, 1898, unmarried. Of Susan and Philip Webster's children, James Ira married Emma Ripetoe, in Illinois, and died in Indiana; John William died young; Amanda Jane married, 3rd Sept., 1868, in Indiana, Daniel B. Shank, (b. in Ohio, Oct. 8, 1838, d. Aug 20, 1924), son of Daniel Shank of Augusta County, Virginia, and wife Elizabeth Conway, removed to Coffeyville, Kansas, and had: Anna Myrtle, b. Dec. 22, 1871, m. Rev. Frank F. Walters, and Hattie Estella, b. Dec. 18, 1877, drowned June 15, 1890; Barbara Ann married Frank Warren Warner, (d. 1927), Mary Elizabeth died in infancy.

page 134:

One of the early New Castle County, Delaware, families was that of Valentine Hollingsworth, a Friend, who came over from County Armagh, Ireland, in 1682. Abraham, his grandson, was among the prominent Friends first in Old Frederick County, Virginia, He died in 1748. (See, Descendants of Valentine Hollingsworth, Sr., by J. Adgar Stewart, 1925.)

page 112:

Alexander Ross was given the right to lay out contiguous tracts not exceeding 100,000 acres 'from such waste land not embraced in any order theretofore made.' This grant was very liberal and general, and did not limit the time as to when the families would have to be seated, which later caused confusion and litigation. Ross's surveys were located on the west side of the Opequon, in the section now north of Winchester, and never aggregated 100,000 acres, as he ran into the Van Meter land. The first grant confirmed to him appears November 22, 1734, for 2,373 acres, part of a 40,000 acre survey of the same year…