Valentine Hollingsworth, the founder of the family in America, was born "about the Sixth Month in the Year 1632," as shown by the ancient records of the Society of Friends, in County Armagh, Ireland. He was a son of Henry and Catherine (Cornish) Hollingsworth, of Ballineskcrannell, parish of Segoe, County Armagh, Ireland, who it is believed emigrated to Ireland from Cheshire, where the family was long seated.

Valentine was an early convert to Quakerism, and suffered severe persecutions for his faith in 1671 and 1672. He married (first), June 7, 1655, Ann Ree, or Rea, (b. 1628, d. Apr. 1, 1671), daughter of Nicholas Ree, of Tanderagee, County Armagh. He married (second) June 12, 1672, at a Friends meeting in the house of Mark Wright, parish of Shenkell, County Armagh, Ann, daughter of Thomas Calvert of Drogora, parish of Segoe, and with her, their three eldest children, his daughter Ann, by his first marriage, and her husband Thomas Conway, came to America in 1682, it is said with William Penn, in the "Welcome."
(Incorrect: The name of his first daughter was Mary Hollingsworth, who married Thomas Conway. - Cathy Ann Carr)

They settled on a plantation of 1000 acres on Shelpot creek, Brandywine Hundred, New Castle county, now in Delaware, about five miles northwestwardly from the present city of Wilmington, where Valentine died in 1710.

The early meetings of Friends were held at his house, and later a meeting house erected on his land and a monthly meeting established, known as "New Worke Meeting," which later became Kennett Monthly Meeting, Chester county. In 1687, Valentine Hollingsworth donated "unto friends for a burying place halfe an acre of land for yt purpose," as shown by the records of said meeting.

Valentine Hollingsworth was a representative from New Castle county in the first Provincial Assembly of Pennsylvania, 1682-3, and in the subsequent assemblies of 1685, 1687, 1688, 1689, 1695 and 1700, and was also a justice of the county from February 7, 1685 to his death. His wife Ann died October 17, 1697.

Two sons, Henry and Thomas, and another daughter, Catharine, with her husband George Robinson, all by the first wife, followed him to the Delaware; and he had seven children by his second wife Ann Calvert.

Henry Hollingsworth, eldest son of Valentine and Ann (Ree) Hollingsworth, was born at Ballineskcrannell, parish of Segoe, County Armagh, Ireland, November 7, 1658. He did not accompany his father and stepmother to the Delaware in 1682, but followed them in the "Lion, of Liverpoole," which arrived in the Delaware river, October 14, 1683.

He came with Robert Turner, the Dublin merchant, who was an intimate friend of William Penn, and a large purchaser of land in Pennsylvania. With him, Henry Hollingsworth served two years, and then took up his residence with his father in New Castle county. He, however, returned to Ireland, as soon as he was comfortably established and married, in his native parish of Segoe, August 22, 1688, Lydia Atkinson, the sweetheart of his youth, and returned immediately with her to the Delaware and located near his father in New Castle county, which county he represented in the Provincial Assembly in 1695.

At about this date, however, he seems to have located in Chester county, Pennsylvania, of which he was elected sheriff in the autumn of 1695. He was deputy-master of rolls there in 1700, and filled the offices of coroner, clerk of courts and deputy surveyor, being directed in 1699, in the latter capacity, by William Penn to survey a large tract of land, some 30,000 acres, for his daughter Letitia, later known as Letitia's Manor, located in Chester and New Castle counties. He removed to Elkton, Cecil county, Maryland, prior to May 9, 1712, on which date he was appointed by Lord Baltimore, surveyor for Cecil county.

His book of surveys, containing a medley, of poetry, receipts, notes on astrology, alchemy and chemistry, in addition to his notes of surveys made, is still in existence, being lately owned by Ex-Governor Samuel Pennypacker. It indicates that he was a man of high scholastic attainments both in the sciences and classics, much of the miscellaneous matter being written in Latin.

He died at Elkton, April or May, 1721, leaving six children, two sons, Stephen, long a magistrate of Cecil county, later removing to the Shenandoah valley, Virginia; Zebulon, of whom presently; and four daughters, Catharine, Ruth, Abigail and Mary.

Captain Zebulon Hollingsworth, second son of Henry and Lydia (Atkinson) Hollingsworth, born in 1696, presumably in Chester county, Pennsylvania, was prominent in the affairs of Cecil county, serving many years as a justice of her courts, filling the position of presiding justice in 1742 and for several subsequent years. He was appointed in 1743 to lay out the town of Charlestown. He was one of the prominent members of the church in St. Mary Ann's parish, erected at North East in 1740, by Samuel Gilpin, and was one of the vestry thereof from 1742 to his death, August 8, 1763. He was a large landowner as well as a miller, manufacturing large quantities of flour, which was shipped to Philadelphia and other points, his sons Levi and Colonel Henry being later associated with him in this business, the former locating in Philadelphia, where the firm carried on an extensive business, which on the death of the father devolved upon Levi, who continued to reside in Philadelphia, and was prominently identified with public affairs there during the Revolution.

Zebulon Hollingworth was buried in the old family burying ground, near the Episcopal church at Elkton, on the banks of the river Elk, but in 1883 his remains were removed to Elkton Cemetery. He married (first) June 18, 1727, Ann, daughter of Colonel Francis Maulden, of Cecil county. She died in 1740, leaving five children, and he married (second) Mary Jacobs, by whom he had six children.

Colonel Henry Hollingsworth, son of Captain Zebulon and Ann (Maulden) Hollingsworth, and father of Mary (Hollingsworth) Gilpin, was born at Elkton, Maryland, September 17, 1737. Well educated and of fine business ability and training, and in the prime of his life of usefulness and activity, at the beginning of the struggle for independence, he was called upon to take an active part in that struggle. His name appears on the records of the Committee of Safety of his native state as one who was relied upon in all its urgent emergencies. He was commissioned January 3, 1776, as Lieutenant-Colonel of the Elk battalion, of Cecil county militia, and was commissioned Colonel, June 7, 1781.

His usefulness however lay more particularly, in the commissary department, and in the organizing, equipping and forwarding much needed recruits, looking after the forwarding and furnishing supplies for the troops in the field, and the general supervision of affairs pertaining to the army for his section. His voluminous correspondence, much of which remains in the Hollingsworth mansion erected by him, and still occupied by his descendants, shows that he was in constant communication with the heads of the various departments both state and national, and was relied upon to fill many important commissions.

This correspondence includes letters to and from Timothy Pickering, by order of the War Office, Charles Carroll, of Carrollton, president of the Council of Maryland, who, on July 13, 1776, writes to him to secure 400 bayonets and other equipment for the Maryland troops, from Patrick Henry who in 1779 sends him fifteen Highland prisoners of war, from Generals Lafayette, Lord Stirling, Nathaniel Greene, and Horatio Gates, and other prominent commanders, principally on the providing of munitions of war, of which Colonel Hollingsworth was one of the first manufacturers.

He was commissary-general for the Eastern Shore of Maryland during the greater part of the war, and had charge of the purchase and forwarding of flour and other provisions for the army in Virginia and Maryland, which by a letter from Timothy Pickering in 1778 he is directed to collect at the Head of the Elk and in Harford county. September 24, 1781, he was directed to make a tour through the Eastern Shore to see that the several requisitions of the board of war for supplying the army were put into execution, and the flour and other provisions collected at points on the navigable waters and shipped as soon as practicable for the use of Washington's army on its southern expedition against Cornwallis in Virginia.

The Hollingsworth mansion, erected by Colonel Henry Hollingsworth early in the eighteenth century, was one of the first houses erected on the site of Elkton, the present county seat of Cecil county, Maryland. It is a venerable pile, in a remarkable state of preservation, picturesquely situated upon a naturally terraced hill near the centre of the town, of ample proportions and built in the sedate colonial style. Its lofty porch is supported by round columns; its gabbled roof and keystone lintels bespeak its colonial origin; the interior retains much of its original design; the ceilings are high, the woodwork heavy and of antique design, and carved corner cupboards with circular shelves and brass-hasped hinges and knobs of the doors add unique ornamentation.

"Separate and to the east of the mansion proper stands a quaint two-storied, two-roomed building--the office. About the walls of the lower apartment are book shelves, while in both rooms are deep fireplaces and inglenooks suggesting quiet comfort. Here indeed was a retreat for the book lover, a haven of rest for the weary."

It was from this historic residence that the theodolite belonging to Colonel Hollingsworth's grandfather, Henry Hollingsworth, the noted surveyor appointed by Lord Baltimore and used in laying out the city of Philadelphia, was taken by the British soldiers when marching from the Chesapeake to attack Philadelphia just before the battle of Brandywine.

Here remained intact until 1898, all the beautiful old furnishings of the period of its construction, including the family silver, cut-glass, and monogramed china handed down for generations. Tarnished coins, musty papers of historical value, implements of antique design long since dulled by rust, and the cradle that rocked the heroes to be, now gathered to their fathers, laurel-crowned. The house was occupied by Colonel Hollingsworth until his death, September 29, 1803, when it passed to his descendants of the Partridge family.

At the death of their last representative in 1898, it was sold and purchased by a descendant of his daughter Mary Husbands (Hollingsworth) Gilpin, and is still retained in the family. Among the papers accumulated there, were the original proceedings of the first Maryland state assembly; a copy of the proceedings of the Maryland convention held at Annapolis, August 14, 1776, to which both Joseph Gilpin and Colonel Henry Hollingsworth were delegates, printed in 1778.

One of these was the property of Joseph Gilpin and is now in possession of his great-great-grandson, William P. Gilpin, the subject of this setch. There were also a great number of other papers of remarkable historic interest, most of which are still in the possession of the family.

Colonel Henry Hollingsworth married (first) in 1769, Sarah (b. Sept. 21, 1748, d. Dec. 27, 1775), daughter of William and Mary Husbands of Cecil county, Maryland, by whom he had three children:--Mary Husbands Hollingsworth, (b. Apr. 26, 1772, d. Nov. 21, 1850), married (first) John Gilpin, above mentioned, and (second) March 31, 1819, Frisby Henderson, of Frenchtown, Cecil county, Maryland; William Hollingsworth, and a child that died in infancy.

He married (second) February 14, 1776, Jane Evans, (1749-1835) by whom he had four children, none of whom left issue except, the eldest, Hannah, (1782-1844) who married James Partridge, (1775-1835), whose heirs occupied the Hollingsworth mansion until 1898.

Henry Hollingsworth Gilpin, son of John and Mary Husbands (Hollingsworth) Gilpin, was born at Elkton, Maryland, March 23, 1804, and died there April 7, 1857. He married Margaret Whann (b. Mar. 17, 1812, d. Aug. 7, 1881), daughter of William Ricketts, of "Union Mills," Cecil county, Maryland, (b. 1778, d. 1838), and his wife, Mary Whann, (b. 1783, d. 1852); granddaughter of Benjamin Ricketts, (1749-1795), and his wife Susanna; great-granddaughter of Thomas Ricketts and Mary, of Hunt Hill, Cecil county, Maryland, (1703-1773).

William Ricketts Gilpin, second son of Henry H. and Margaret W., (Ricketts) Gilpin, was born at Elkton, Maryland, November 11, 1834. He married September 11, 1856, Anna Eliza (b. Nov. 6, 1839, d. Oct. 8, 1899), daughter of Aaron C. and Eliza Engle of Philadelphia, Pennsylvania.