Loudoun County, Virginia, 1859

Graysons in the Lead up to War

Benjamin (ca. 1684-1757) and Susannah (Monroe) Grayson (ca. 1695-1752), our colonial forebears, had four children together: Benjamin Grayson II (ca. 1730-1768), our ancestor Rev. Spence Grayson (ca. 1734-1798), Col. William Grayson (ca. 1736-1790), and Susannah Monroe Grayson Orr (ca. 1742-1780). Between them, they had hundreds of descendants by the time of the U.S. Civil War.

Lt. Thomas Gedney, Col. Peter Grayson

Susannah Orr’s granddaughter Hebe Grayson Stewart (1801-1853) was married to Lt. Thomas Gedney (1799-1857). Her husband not only reportedly subdued the failed assassin of Andrew Jackson at the U.S. Capitol in 1835, but in 1839 he also commanded the U.S. Navy brig that intercepted the schooner Amistad off the coast of Long Island, touching off an international legal battle. U.S. Army Col. Peter Grayson (b. 1770), son of Rev. Spence, was “a warm and personal friend of General Jackson” under whom he “served at New Orleans as Adjutant General of the Tennessee troops, and soon after his return home died of disease taken there in 1816.”¹

Gen. John B. Grayson and Capt. John B. Grayson, Jr.

A grandson of Col. William Grayson is the most notable Civil War military descendant. Gen. John Breckenridge Grayson (1806-1862) was first cousin to U.S. Vice President, 1860 Presidential candidate, and Confederate Secretary of War John C. Breckenridge. A West Point graduate and Confederate brigadier in command of troops in Florida, Gen. J.B. Grayson contracted tuberculosis and pneumonia and died in October 1862. His son Capt. John B. Grayson Jr. (1835-1897) was a Confederate artillery officer captured and paroled at the surrender of Vicksburg on July 4, 1863, then again in Alabama at war’s end in April 1865. J.B.G. Jr. put together a family history in 1877, a line of which, seen below (with my emphasis added), is the inspiration for this latest research.

Children of Benjamin Grayson II and III

“Benjamin Grayson, the third, married a Miss Brohaugh of Loudoun. He left a large family and five estates. His sons were the late Dr. William Grayson of New York, the late Dr. Robert O. Grayson of Stafford, and Dr. Richard O. Grayson of Loudoun, and two (2) daughters, the widows, Mrs. Bettie Carter and Mrs. [Mary] Stevenson [sic], of Loudoun County. All these had children and some are residing in Loudoun County, and some emigrated since the late War to the West. Alexander and Richard Grayson of this branch of the family, were officers in the Confederate States Army and died in battle.¹

Graysons, Carters, and Stephensons of Loudoun County, Virginia

Benjamin Grayson II and his wife had one son. Of the children of Benjamin Grayson III (1763-1835), William (1788-1855) and Robert (1789-1841) had struck out on their own by 1824, borrowing from their father to do so. Bettie (1797-1885), Mary (1801-1887), Richard (1804-1842), and a fourth son, George M. (1795-1858) inherited portions of their father’s estates. Mary Grayson married William Stephenson, a farmer from Ireland, in 1833. The once-widowed and childless Bettie married the older bachelor George Tasker Carter of Oatlands in 1835. Her preserved Civil War-era diary describes in some detail day to day life at Oatlands. Loudoun County in the 19th century was already considered horse country, and dozens of wineries now also dot its still-bucolic landscape. Bordered by the Blue Ridge Mountains, the Potomac River, Fauquier, and Fairfax Counties, Loudoun today remains scenic and charming. Its political landscape began to change dramatically in the 1850s, with John Brown’s failed October 1859 insurrection at Harper’s Ferry rippling uncomfortably through neighboring Loudoun, Fauquier, and an increasingly divided country.

Three Loudoun Cousins

J. Welby Armstrong, Upperville School Principal

J. Welby Armstrong, a native of Longford, Ireland, graduated from Dublin’s Trinity College with a degree in Ancient Languages and Literature, and was working as a teacher in Virginia by 1850. In 1852 he became principal of the Upperville Academy. The village of Upperville, “a mile long and an inch wide”² straddles the Fauquier and Loudoun line. The building used for the Academy still stands.³ Welby Armstrong and his faculty gave classical educations to local and boarding young men for the next seven years, including a number of Graysons, Carters, and Stephensons.

Welby married Mary Grayson‘s daughter Bettie O. G. Stephenson (b. 1838) in 1857. Their daughter May was born in November 1859.

Alexander Grayson, Farmer and Head of Household

Around 1830 George Mason Grayson married the widow Ann Louisa (Fitzhugh) Rose. She had two young daughters and together they had two sons, the oldest of whom was Alexander (b. 1833). George died in 1858, and both girls had married when in 1860 the census lists 27-year old unmarried Alexander in Loudoun as “Farmer” and head of household with his 62-year old mother and 16-year old brother George Jr.

Richard O. Grayson Jr., Orphan and Mining Clerk

Dr. Richard O. Grayson and Maria Margaretta (Fitzhugh), the younger sister of George M.’s wife Ann, were married in 1828. Richard Osborne Grayson, Jr. was the fifth of their six children. By the time Jr. turned four, his parents had died. The 1850 Census finds 12-year old Richard and three siblings living with their widowed Aunt Bettie Grayson Carter at Oatlands with Bettie’s sons George Jr. and Benjamin and an in-house teacher. In September 1860, 22-year old Richard is living at a camp or large boarding house in Greensboro, North Carolina. His 75 fellow boarders were all men, with “Miner” or “Laborer” as primary occupations. Richard stands out as the only man not born in either N.C. or England, and the only “Clerk.” A number of large gold, copper and iron mines surrounded 1860 Greensboro. It appears that Richard, an educated man, was hired to be the accounting clerk.

Thus, in 1859 Loudoun County, we meet four families and three particular Grayson first cousins, the grandchildren of Benjamin Grayson III:

• Bettie Stephenson Armstrong, age 22, a new wife and mother, and her school principal husband J. Welby Armstrong.
• Alexander Grayson, age 26, a Loudoun farmer providing for his recently widowed mother and 15-year old brother.
• Richard O. Grayson, Jr., age 21, orphaned by age 4, raised by his widowed Aunt Betty Carter, and setting off to find his place in the world.

¹ Grayson, John Breckenridge Jr., The Grayson Family (unpublished manuscript, 1877) pg 4

² https://www.visitfauquier.com/town-village/upperville/

³ Available to rent for $635 a night. https://www.airbnb.com/rooms/49838071?source_impression_id=p3_1710172352_CDhw9hyCBBkzwwZy