An American Family History

Benjamin Head

The first European settlement in Orange County, Virginia was in 1714 and the county was officialy formed in 1734 with no western border. In 1738 the western part became Augusta County.

The 24,000 acre Octonia Grant was recorded in 1722. The land is now in Greene and Orange Counties, Virginia. The original eight grantees failed to meet the settlement requirement and the grant was renewed in 1729 to Robert Beverly. William Stanard inherited a significant portion of the Octonia grant in 1756.

The Octonia Stone (Octoney, Octeny, Octona, and Octuna) marks the end of the western boundary. It is near Stanardsville, Greene County, Virginia. The stone is engraved with a figure 8 with a cross touching the top of the 8.


Benjamin Head was born about 1733 in Virginia. He was probably related to Anthony Head and may have been his son. Some researchers believe that his father could have been James Head.

He married Martha Sharman. She was the daughter of Robert and Lucy Sharman of Bromfield Parish.

Benjamin and Martha's children included:

James Head (1758, married Elizabeth Powell),
Sarah Head (1760, married May Burton, Jr.),
William Head (1761, Margaret Kirtley),
Benjamin Head, Jr. (1763),
John Head (1766, Nancy Ann Sanford),
George Marshall Head (1768, married Mildrew Rucker),
Henry Head (1773, married Elizabeth Sanford)
Tavener Head (1776, married Jane Plunkett)

They lived in St. Thomas Parish in Orange (later Greene) County, Virginia. Their home was near Anthony Head and at some time was living with George Head and his wife Elizabeth Dearing).

In 1754, Benjamin was included on the Orange County tithable list with ten tithables. The tithables included enslaved men.

On May 23, 1754, the road orders for area was outside the southern perimeter of the original Octonia grant included Benjamin Head.

Benjamin Head is Appointed Overseer of the Road in the Room of William Lucas, & that he with the Gang that under the said Lucas clear & keep the same in Repair. 

On May 22, 1755, Benjamin bought 200 acres in Bromfield Parish, Culpeper County, Virginia on the north side of the Rapidan River, west of Maple Run from Colonel Thomas and Martha Chew and Timothy Crosthwait. On September 10, 1759, Benjamin sold the 200 acres in Bromfield Parish.

In 1765 and 1767, the road orders for area was outside the southern perimeter of the original Octonia mentioned his land.

On July 1, 1767 and March 22, 1769, Benjamin Head made a winning bid of 307£ for 1,325 acres of the original Octonia Grant owned by Harry Beverley. The deed was granted on November 28, 1771

On August 24, 1773, Benjamin bought 160 acres "at the upper corner of the Rapidan River" from Martha's father Robert Sharman. He sold the land in 1777.

April 18, 1774, Benjamin proved Robert Sharman's will.

In 1774, Benjamin Head sold 450 acres in Orange County to his neighbor Durrett Oliver for 56£ and six pence.

In 1774, Benjamin was appointed overseer of a local road.

Benja. Head Appointed Overseer of the Road in the Room of James Wayt to Clear the Road from the great Run up to a place call'd Boxin Camp

From 1778 to 1779, Benjamin was a captain in the Orange County militia.

Benjamin Head appointed Captain in the room of Jere White, who has resigned. Robert Miller, 1st Lt., May Burton, Jr., 2nd Lt., and Richard White, Ensign.

In 1782, Benjamin was on Thomas Barbour's tithable list. In 1782 there were two Benjamin Heads in Orange County. The other Benjamin Head was on Benjamin Grymes' list. When this Benjamin petitioned to keep an ordinary at Old Trap in 1778 and 1780, Joseph Parish was his security. Joseph Parish was on Grymes' list. This Benjamin's will was proved in Culpeper County in 1790 and was witnessed by Edmund Row. His wife was named Grace and his son Benjamin inherited an enslaved man named Tom.

In 1782, Benjamin had eighteen people in his household. The household included 11 enslaved people.

On February 22 1787, Benjamin sold 265 acres to his son-in-law May Burton, Jr. for 186£, 16 shillings, and six pence.

On November 1 1794, Benjamin bought 195 acres in Orange County from John Ferguson adjoining John Snell and Matthias Smith. Benjamin Head's son John witnessed the deed.

On July 25, 1795, Benjamin sold the remaining 295 acres south of the "great run" to his son John.

On October 21, 1801, Benjamin wrote his will. He left

  • his land and plantation where he lived to his son Tavner after his wife died
  • an enslaved woman named Betty to his daughter Sarah Burton
  • the residue of his estate after the death of his wife, to his sons William, Benjamin, John, George Marshall, Henry, and James (hs representatives).

His sons George Marshall and Henry were named executors. The witnesses were Richard Cave, Benjamin Spicer, and James Alexander.

Benjamin died about 1803.

The inventory of his estate included thirteen enslaved people including Toby, Harry, Peter, Tami, Abram, Pike, Yorke, Syrus, Gabrie, Ann "and her child Clary," Dinah, and Sarah. It also included 8 horses, 42 hogs, 32 cattle, 22 sheep, farm equipment, furniture, numerous personal items, "1 large Bible" and six books.

Martha died in 1821.

Slavery is an immoral system of forced labor where people are treated as property to be bought and sold. It was legal in the American Colonies and the United States until the Civil War.

A tithable was a person for whom a head tax was to be paid. The definition varies over time and place, but generally included members of the potentially productive labor force.
A poll tax is a tax levied on every poll. The definition of a poll also varied, but was generally a man of legal age.

The American Revolutionary War (1775–1783) was between the Kingdom of Great Britain and the 13 colonies which became the newly formed United States.




from Orange County Order Book 7, 28 March 1765, page 263

On the Petition of Henry Beverley for Leave to Turn the road from Beverdam run that goes by Benja. Heads Ordered that John Haskew Wm. Lucas Robert Johnson & Thomas Shackleford or any three of them being first Sworn as the Law Directs do view the said Way that the said road is intended to go and make return to the court of the conveinence & Inconveinences Attending Same


from Orange County Order Book 7, 23 July 1767, page 447

On the Motion of David Vawter to have a Veiw for a road to turn out at the dividing Line between Benjamin Head and Richard Durrett and to keep the Line of the said Heads & Durretts to the River at Crawfords foard Ordered that Robert Johnson, May Burton Jeremiah White and James Wayt or any three of them being first Sworn before a Justice of this County do Veiw the said Way and Make report to the Court of the Conveinences and in-conveinences attending the Same


from Orange County Order Book 8, 23 November 1769, page 47

On the Motion of Robert Johnson to renew his Ordinary Leicence it is granted him he giving Security Whereupon he with Benja. Head his Security Entered into Bond for the Same


from Orange County Order Book 8, 26 April 1770, page 60

Henry White the Younger is appointed Overseer of the Road in the room of Benjamin Head and that he With the Hands that was under the sd. Head do clear the Same precints and keep the same in Good Repair


from Orange County Minute Book 2, 26 November 1778, page 97 

May Burton jr is appointed Oversr. of the Road in the Room of Benja. Head & that the hands of Colo. Thortons Thos. Daughaney, Thos. Ballard & Moreman Ballards be Aded to his Gang


from Orange County Minute Book 2, 28 January 1779, page 98 

On the Pet. of John Moore for a Road from Crawfords foard into the new Road above John Snells Ordered that Jere. White, Benja. Head, May Burton & May Burton Jun or any three do Veiw the sd. Intended Way & make report to the Court of the Same Accordg. to Law


from Orange County Minute Book 2, 23 March 1780, page 126 

On the Petition of Wm. Walker to have a Veiw for a Road from Crawfords ford on the Rapadan into the Road by Robert Sanford Ordered that Jere. White, Ben. Head Robt. Miller & May Burton jr. or any do Veiw the sd. Intended Way and make report Accordg. to Law

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©Roberta Tuller 2020
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