Pvt. John "The Highway Man" Rosamond

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Pvt. John Roseman (Rosamond)

Also Known As: ""The Highwayman"", ""The Highway Man""
Birthplace: Poss County Leitrim, Ireland
Death: circa 1789 (71-87)
Abbeville, Abbeville County, South Carolina, United States
Immediate Family:

Son of Sergeant James Rosemond; Sgt. James Jacob Roseman / Rosamond; Ann Rosamond and Ann Roseman / Rosamond
Husband of Sarah Rosamond and Sarah Wilson Rosamond
Father of James Roseman / Rosamond; Margaret Weems; James Rosamond; Jean Rosamond; Capt Samuel Rosamond and 1 other
Brother of Nathaniel Rosamond and Unknown Rosemond

Occupation: Master shoemaker, soldier
Managed by: Marsha Gail Veazey
Last Updated:

About Pvt. John "The Highway Man" Rosamond

(1) Source: Jimmy Rosamond <jdrosamond@comcast.net>.

(2) Jon Presco <http://rougeknights.blogspot.com/2008/10/highwayman-is-free-images-hi gwayman.html>:

In 1724, . . . John ROSAMOND and his friend William Ray were arrested in Abingdon, Berkshire, England for stealing a hat, periwig, 30 pounds British sterling, five pairs of shoes, and a brown gelding. They were held in the gaol in Reading, Berkshire, after their trial where they were sentenced to be exiled to the colonies for 14 years hard labor. By March 1725, they were transported to Newgate Prison and held there until they boarded the convict ship "Forward" owned by Jonathan Forward, and captained by Daniel Russell. The ship set sail on 28 September 1725 from London via the Thames River. The ship arrived [and] disembarked at Annapolis, Maryland on 8 December 1725. We don't know who bought his indenture, but he is recorded as being in CPT Beall's militia of Prince George Co, Maryland between 1734-1737. By 1747-1765 we find John ROSAMOND living in Augusta Co, Virginia and listed as a master shoemaker, owned land, paid tithes, served in the militia, etc.

(3) Coldham, Peter Wilson, Bonded Passengers to America, 9 Volumes in 3, Baltimore, MD: Genealogical Publishing Co., 1983, Vol. 6, Oxford Circuit, 1663-1775: Berkshire, Gloucestershire, Herefordshire, Monmouthshire, Oxfordshire, Shropshire, Staffordshire, and Worcestershire, p. 9:


Ray, William. S Lent R 14 yrs Summer 1725 for highway robbery LC from Forward at Annapolis, Md, December 1725. . . .

Rosamond, John. S Lent R 14 yrs Summer 1725 for highway robbery LC from Forward at Annapolis, Md, December 1725.


LC - Landing Certificate issued at the colonial port of entry, followed by the date of issue.

R - Reprieved on condition of transportation to the American colonies. In the case of those reprieved for 14 years or of life transportation, this is noted where it appears in the records; otherwise the term imposed was normally seven years.

S - Sentenced to be transported to the American colonies for a period of seven years unless otherwise stated, followed by the date of the Sessions at which the trial took place.

(4) Christianson, Scott, With Liberty for Some: 500 Years of Imprisonment in America, Boston, MA: Northeastern University Press, 1998, pp. 23-24:

In 1717 Parliament passed an act empowering courts to sentence offenders directly to transportation. Persons convicted of clergyable felonies or petty larceny could now be sent to American plantations for seven years instead of being whipped or burnt on the hand. This meant that a large portion of England's offenders were eligible to be shipped abroad and sold as servants for seven-year terms. Felons convicted of capital crimes could, with royal consent, be commuted to a term of fourteen years' transportation or, in some cases, life. Anyone who returned before her or his term expired or who helped a convict to escape was liable to be hanged.

Jonathan Forward, a young London merchant with extensive contacts in Maryland, obtained a lucrative subsidy of three pounds for every Newgate felon and five pounds for every convict taken from the provinces. In exchange, he agreed to ship any and all criminals sentenced to transportation, and to pay all costs, including gaol fees, for their conveyance. Forward was experienced in the African slave trade and had recently shipped two vessels with 171 convicts to Maryland. Operating out of his Cheapside house on Fenchurch Street, London, he collaborated with Jonathan Wild, who helped to provide "felons" for shipment abroad.

On April 26, 1718, 29 malefactors at the Old Bailey were ordered to be transported. Four months later the Historical Register reported that 106 convicts "that were ordered for transportation, were taken out of Newgate and put on board a lighter at Blackwall Stairs, from whence they were carried through the Bridge to Long Reach, and there shipped on board the Eagle galley, Captain Staples commander, bound for Virginia and Maryland. (The Eagle was a well-known slave ship that had sailed for the Royal African Company for more than a decade, so the transport of prisoners to America was nothing new for her.)

Forward retained his monopoly for over twenty years until April 1739, when Andrew Reid was added to the payroll. Although Forward continued to transport felons from provincial gaols until the late 1740s, Reid assumed main control of the convict trade.

(5) Bailyn, Bernard, Voyagers to the West: A Passage in the Peopling of America on the Eve of the Revolution, New York, NY: Vintage Books, 1988, pp. 262-263:

For thoughtful Americans concerned with the character of American society, the banishment of convicts to America was an abomination, and for those with an eye for macabre humor it was ludicrous. The most famous comment on the problem was [Benjamin] Franklin's proposal-published after a crime wave, perpetrated in Virginia, Maryland and Pennsylvania chiefly by convict servants, was luridly reported in the press-that the colonies should be authorized to "transport" their rattlesnakes to Britain in exchange for "the human serpents sent us by the mother country."

(6) Jimmy Rosamond <jdrosamond@comcast.net>:

Researchers [have] assumed that John relocated to Virginia where he married Sarah Wilson. . . . John and Sarah relocated their family to the Abbeville District of South Carolina no later than 1765.

The first instance of John being in Virginia is from Chalkley's Chronicles showing him in Augusta County in 1747. Then in 1765, there is a record in Chalkley's that says the property he and Sarah owned was sold to them by a man who didn't own the property himself. This apparently caused a problem, because the final record in Chalkley's shows them selling the land to someone else with the court's permission. The next record of him is a land grant dated 1767 in Abbeville District, SC. That dates their move to SC between 1765 and 1767.

John was a master shoemaker in Augusta County, VA in the 1750s. This is documented in Chalkleys.

(7) Caution: Based on a will which Jimmy Rosamond <jdrosamond@comcast.net> has found for a John ROSEMAN in Prince George's County, MD, proved in 1789, John "The Highwayman" ROSAMOND may have lived out his life and died in Prince George's County, MD. If this proves to be true, the John ROSAMOND who lived in Augusta County, VA is probably not the same person as John "The Highwayman" ROSAMOND.

(8) John ROSAMON, John ROSAMOND, John ROSEMAN, John ROSEMAND, John ROSEMOND, John ROSMAN and John ROSMOND are mentioned in Chalkley, Lyman, The Chronicles of the Scotch-Irish Settlement in Virginia: 1745 to 1800 [Reprint, Originally Published, 1912], Baltimore, MD: Genealogical Publishing Co., 1980 <http://www.rootsweb.ancestry.com/~chalkley/>. The compiler assumes that all of these Johns were the same person, namely, John ROSAMOND. Set forth below are all of these references from Chalkley, with the capitalization of John's surname added by the compiler:

Volume I, p. 39:

AUGUST 24, 1749.

John ROSEMOND added to tithables.

Volume I, p. 120:

APRIL 15, 1765.

James Bell, provisions. Wm. Bell, provisions. Wm. McCutcheon, provisions and horse impressed. John ROSEMOND, provisions. Andrew Cowan, enlisting men to garrison Fort Lewis. Walter Trimble, provisions. Thos. Alexander, provisions. John Francis, provisions. James Kirk, provisions. Rob. Armstrong, provisions. Wm. Christian, self et als., ranging. Loftus Pullen, provisions. Rob. Christian, provisions. Danl. O'Freild, provisions. Thos. Poage, provisions. Charles Kilpatrick, provisions. George Moffett, for Wm. Mann et als. Benj. Estill, horse impressed. Andrew Hamilton, provisions. Wm. McClenachan, provisions. Wm. McKarney, self et als., ranging.

Volume II, pp. 414-415:

1750-Sam'l Akerlin, gone to Pennsylvania; Gabriel Akerlin, gone to Pennsylvania; Jeremiah Bates, can't find; John Boaman, can't find; Edward Boil, gone to Carolina; Jno. Bolin, not found; Wm. Crisp, to Carolina; Edw'd Cochran, runaway; Pierce Castlan, lives in Lunenburg; Philip Linch, runaway; Robt. Crumbe, twice charged; Nath'l Cherry, not found; John Droen, not found; John Doson. to Carolina; James Dailey, runaway; Rob't Fryer, not found; James Gordon, no effects; Rob't Gamble, not found; Chas. Gilham. not found; David Galloway, twice charged; Naftalin Gregory, not found; Wm. Hardgrove, to Carolina; Elias Hamilton, not found; Joseph Hendon, not found; Wm. Hall, twice charged; Wm. Hambleton, not found; Benj. Hardin, twice charged; Wm. Henry, to Carolina; Wm. Inglish, Constable; Melchisedick Johnston, not found; Martin Kelley, no effects; Wm. Terrey, Constable; Ro. Teat, gone to Carolina; Benj. Thompson, not found; Bryan White, runaway; Alex. Walker, Constable; Thos. Wilson, twice charged; Ben. Young, not in this County; Rob't Lockndge, Constable; Jno. McFarland, Constable; Jno. McClenachan, Constable; Henry Leonard, not found; John Lawler, to Carolina; Geo. Maison, not found; Henry Miller, not found; Jno. McCurry, Jr., not found; Joseph McCurry, runaway; James Murphy, runaway; Neal McNeal, twice charged; Hugh McBride, runaway; James McAffee, twice charged; Arch'd McCleerie, not found; Hugh Maires, not found; Wm. McLehanny, not found; Jno. McHunis, not found; Jas. McCrenneld, not found; Abraham Mires, not found; Rob't Mains, not found; Jno. Mills, dead, and no effects; Jacob Martin, twice charged; poor John Hance, not found; Jno. Potts, twice charged; James Ryan, not found; Jno. Ramsey, twice charged; James Robeson, twice charged; Sam'l Stalnaker, lives at Holston River; Jno. Scott, thrice charged; Jno. Shields, lives at Rockfish; Jno. Stevenson, twice charged; James Scot, twice charged; Jno. Stanley, not found; Jno. Vance, lives in Lunenburg; Elias Wallraven, not found; Nath'l Wilsher, not found; Wm. Walker, twice charged; John Walker, gone to Carolina; John Warnock, twice charged; James Gay, Constable; James Mais, Constable; David Miller, Constable; Jno. ROSMOND, Constable.

Volume II, p. 463:

1760: Processioned in Capt. Moore's Company by John Stephson, Nathaniel Evins: For Nathaniel Evins, for Wm. McCreerey, for Thos. Willson, for John Stevenson, for John McClung, for Wm. McClung, for Alex. Moore, for Adam Reed, for Wm. Hays, for Wm. Paris, for Thomas Bard, for John Cunningham, for Mathew Huston, for John Mountgumery, for Wm. Moore, for Wm. Lockridge, for Thomas Boyd, for John Boyd, for Thomas Hill, for Robert Ware (Wire), for Wm. Hays, for Wm. Beard, for Wm. Wardlaw, for Andrew Steel, for James Steel, for Joseph Kennedy, for John Lowry, for Samuel Huston, for James Eakins, for John Hanly, for John Logan, for Alex. Logan, for Alex. McNutt, for James McNutt, for John ROSMAN, for Andrew Dunkin, for John Wardlaw, for Wm. McCanless, for James Cowdan, for John Moore.

Volume III, p. 15:

28th October, 1749. James McNutt's appraisement by James Trimble, Joseph Coulton, John ROSEMAN. Notes of Philip Chittam, Jas. Davis and Arthur Miliken.

Volume III, p. 26:

21st September, 1750. John Greer's vendue. Sold to John Lockhart. John ROSEMAN, Sarah Lynn, John Teat, John Mitchell, Christopher Kelly, George Breckinridge, Thos. Scott, James Lynn, Thos. Teat, Francis Beaty, John Mitchell.

Volume III, pp. 29-30:

23d May, 1751. James McNutt's orphans. Settlement by Thos. Beard, administrator. Paid Mr. Burden for 185 acres bought by my wife (Thos. Beard's?) now, but before marriage. 17__ to Mr. Burden quit rents on 85 acres for 10 years. 1747 to Mr. Downs for quit rents. 1744 to Mr. Burden for quit rents, 300 acres. December 20th, 1748, paid David Hays rents debt due before marriage. Paid Wm. Nutt debt. 8th May, 1749, paid Wm. Hunter for work. 4th February, 1747, paid John Huston, debt. 9th December, 1748, paid John ROSEMAN. debt. 10th May, 1748, paid Saml. Wilson, for bringing some linen from Penna. Paid to Widow Sheals, a debt. Paid to Robt. Alexander, for schooling James and Robert McNutt. Paid to James Dobbins, for schooling Alex. McNutt. Paid one new Bible, for Alex. McNutt. Paid one new Testament, for James McNutt. Paid one new spelling book, for the children.

Volume III, p. 54:

20th September, 1758. Vendue of John Snodgrass' estate, by Agnes Patton-To David Edmund, Wm. Parris, Robt. McRandolph, John Wardlaw, Wm. Adair, Peter Angel. Paid to John Mountgomery, Edmond Tarr, James Henry, Jno. ROSAMOND, Patrick Hays, James McCown, Andrew Steel.

Volume III, p. 306:

Page 456.-19th August, 1752. Joseph Kennedy to John ROSEMAN, 380 acres, 20 poles. Moffett's Creek. Teste: Wm. Wilson, James Walker, Fr. Beatey.

Volume III, p. 311:

10th February, 1753. Same [Borden, etc.] to Thomas Beard, 605 acres of 92100; Moffett's Creek of James; corner John ROSEMAN. Delivered: Saml. Buchanan, 21st June, 1758.

Volume III, p. 335:

24th _____, 1755. Daniel McBride puts himself apprentice and servant to John ROSEMAN. cordwainer or shoemaker, for 2 years. Teste: Ro. Armstrong (mark) and James Goodly.

Volume III, p. 344:

15th June, 1754. George Henderson to John ROSEMAN, £60. Bill sale conveys all horses and cows, sheep and hogs, all movable goods and chattels. Teste: Wm. Wardlaw, Robert Henry. Acknowledged, 17th November, 1756.

Volume III, p. 359:

18th March, 1760. Thomas Beard and Margaret to William Beard, £100, 605 A., 1 R., 28 P., in Borden's tract, on side Moffet's Creek; corner Jno. ROSEMAN's land. Delivered: Wm. Beard, August 12, 1791.

Volume III, p. 383:

5th February, 1762. George Henderson to Hugh Wardlaw, £60, 284 acres in Bordin's tract, on Moffett's Creek; cor. John ROSEMAN; cor. Wm. Wardlaw, James Wardlaw's line. Teste: Henry Long.

Volume III, p. 433:

14th October, 1765. Same [Borden's executors] to Robert Gay, 100 acres, part of 92,100, oak on Moffet's opposite John ROSEMAND's old survey, opposite George Henderson's land, post in the Barrens. Delivered to Robert and Archibald Rhea, devisees, 17th January, 1803.

2d October. 1765. George Patterson, eldest son and heir of John Patterson, to John ROSEMAN, £30, 380 acres on Moffet's Creek. David Mitchell.

Volume III, p. 436:

October, 1765. John ROSEMAN and Gabriel Jones to George Patterson, £150. Bond conditioned, whereas John Patterson, late of Augusta, deceased, father of George Patterson, was seised of 380 acres which he sold to Joseph Kenedy, but never made title, and Joseph sold to John Koseman for £45.10, and either mistake or design the said Kennedy conveyed to John ROSEMAN, 19th August, 1752. though the title was in Patterson and devolved upon the above named Geo. Patterson as eldest son of John, and George has conveyed to John ROSEMAN; if John and Gabriel keep said George safe of law suits, troubles, &c., then to be void.

10th October, 1765. John ROSEMAN and Sarah to Robert Gay, £120, 380 acres, 20 p., on Moffet's Creek. Teste: Francis Railey. Delivered: Robt. Rhea, one of the devisees, 17th January, 1803.

[Note by compiler: Chalkley is not without its problems, as Daphne Gentry of the Publications and Educational Division of the Library of Virginia has pointed out. (See http://www.lva.lib.va.us/whatwehave/local/va5_chalkleys.htm.) Not all documents are included. There are not only errors of omission, but errors of transcription have also been documented. This simply means that the careful researcher should send for a copy of the original document, as with any secondary source, and should not assume that because it doesn't appear in Chalkley it does not exist.]

(9) Brown, Katherine L., New Providence Church, 1746-1996, A History, Raphine, VA: New Providence Presbyterian Church, 1996, p. 42 (transcript provided to the compiler by Jimmy Rosamond <jdrosamond@comcast.net>):

In the absence of session records for the first sixty years of the life of New Providence Church, this signed call and the first subscription list are highly significant documents. The 1753 call is not divided by congregation, but the separate lists for New Providence and Timber Ridge for 1754 and 1755 can be compared with the names on the call. There were a total of forty-six names on the New Providence salary list, thirty-four in 1754, all of whom renewed their support the next year, and twelve additional names in 1755. The pledging founders of New Providence Church are William and Thomas Berry, Samuel Buchanan, James Coulter, Robert Culton, James Eaken, Walter Eaken, John Edmiston, William Edmiston, Robert Gamble, John Handly, George Henderson, Thomas Hill, John Houston, Matthew Houston, Samuel Houston, Joseph Kennedy, John Logan, James Lusk, Edward McColgan, McCroskey, Samuel McCutchan, Alexander Miller, John Montgomery, Alexander Moore, James Moore, Patrick Porter, Robert Reagh, William Reagh, James Robinson, Matthew Robinson, John ROSEMAN, Widow Smith, William Smith, Andrew Steele, John Stewart, James Trimble, Alexander Walker, James Walker, John Walker, William Wardlaw, Robert Weir, and Ann Wilson. In addition, there were nine names on the call that did not pledge, but who were closely associated with New Providence. They were Charles Berry, Samuel Dunlap, James Edmiston, Samuel Hay(s), McCrosky, William Reagh, William Robinson, Samuel Steel and John Wardlaw. [Capitalization of John ROSEMAN's surname supplied by the compiler.]

Most of those pledging contributed fifteen shillings up to one pound, but there were a few pledges larger than that. Andrew Steele, who traveled to New Castle Presbytery to present the call, pledged two pounds, three shillings and four pence.

(10) Morton, Oren Frederic, A history of Rockbridge County, Virginia, Staunton, VA: The McClure Co., Inc., 1920, pp. 34-35:

THIS INDENTURE made the twenty fourth Day of _____ in the year of Our Lord Christ one thousand seven hundred and fifty five WITNESSETH that Daniel McBride of the County of Augusta in the Colony of Virginia hath Put himself apprenting Servant and by these presents Doth Voluntarily Put himself and of his own free will & accord put himself apprenting servant to John Roseman Cordwainer or shoemaker of this sd County of Augusta in the Colony aforesd to Learn his art and Trade or Mystery after the manner of an apprenting servant to sarve him or his assigns from the Day of the Date hereof for & During the full Term and Time of two full years next ensuing, During all what time the sd apprentice his Said Master faithfully shall Serve his secret Keys his Lawfull Commands very _____ gladly obey he shall Do no Damage to his said Master nor see it Done by others with out Letting or giving notice thereof to his said Master he shall not wast his said Master's goods nor lend them unlawfully to others he shall not Commit fornication nor Contract Matrimony within the sd Term at Cards or Dice or any other unlawfull games he Shall not play whereby his said Master may be Damaged with his own goods or the goods of others During the sd Term without the License of his sd Master he Shall Nither Buy nor Sell he Shall not absent himself Day nor Night from his sd Master's Service without his Leave nor haunt ale houses still houses Taverns or play Houses but in all things Behave himself as a faithful apprentice Savant ought to Do During the sd Term & Time and the sd Daniel McBride doth hereby Covenant and Declare himself Now to be of the age of Nineteen years a single Person & no Covenanted Indented or Contracted Servant or apprentice to any persons or persons whatsoever and the sd Master Shall use the utmost of his Indeavors to Teach or Cause to be Taught & Instructed the sd prentice in the Trade and Mystery he now professes Occupieth or followeth and procure and provide for him the sd apprentice sufficient meat Drink apparel washing and Lodging fitting for an apprentice During the sd Term and at the End & Expiration thereof the sd master shall pay unto the sd prentice the sum of Ten pounds Current Money of Virginia or the value thereof in goods or Chattels and for the true performance of all & every this sd Covenant & agreement Either of the said Parties binded them selves to the other firmly by these presents IN WITNESS whereof they have hereunto Interchangeably set their hands and affixed their seales the Day and Year first above written.

[Note by compiler: Rockbridge County, VA was formed from Augusta and Botetourt Counties, VA in 1778.]


1. In 1925 William Sam Rosamond did a relatively complete genealogy. His research indicated that we were descended from a Huguenot born in France sometime in the mid to late 1600s. He discovered that his earliest traceable ancestor was a "Sergeant" Rosamond who left France following the Revocation of the Edict of Nantes on 22nd October 1685. He found that Sergeant Rosamond supposedly travelled to Holland where he joined the army of William III, went to England, and from there went with William's army to Ireland. He fought in the Battle of the Boyne on 1st July 1690 (by the old calendar – 12th July by the new calendar) and then remained in County Leitrim, Ireland. (There is still a family of Rosamonds in County Leitrim.) He had three sons, two of whom went to the American colonies and settled in the mid-Atlantic region. One of the sons’ names was either John or Thomas Rosamond. Current researchers have not been able to confirm this connection. It appears probable that the American branch of the family are descended from John "The Highwayman" Rosamond who arrived in Annapolis, Maryland in 1725. He was sentenced to be transported into 14 years servitude for robbery from the Oxford Assizes. This John could be the son of Sergeant William Rosamond, and the mix up in names likely stems from the fact that his father-in-law's name was Thomas Wilson.

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Pvt. John "The Highway Man" Rosamond's Timeline

Poss County Leitrim, Ireland
September 11, 1715
Age 5
London, Greater London, England, United Kingdom
Age 35
Augusta County, Virginia
December 9, 1748
Age 38
Augusta County, Virginia, Record of payment of debt from estate of James McNutt
Age 40
Augusta County, Virginia; John Rosmond listed as Constable filing list of tax delinquents for the year 1750.
Age 41
Augusta County, Virginia
Age 44
Abbeville, Abbeville County, South Carolina, United States
Age 44
Prob Augusta County, Virginia