Col Richard Callaway

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Richard Calloway, Col.

Birthplace: Madison, Kentucky, United States
Death: Died in Boonesborough, Kentucky, United States
Immediate Family:

Son of Joseph Callaway, Jr. and Catherine Ann Callaway
Husband of Elizabeth Hoy Calloway and Frances Callaway
Father of Zachariah Callaway; Mildred Noel; Nancy Anna Gilchrest; Sarah Penn; Mary Gwatkin and 7 others
Brother of Elizabeth Bramblett; Joseph Callaway; John Callaway; William Callaway; Thomas Callaway and 5 others

Managed by: Steve Poland
Last Updated:

About Col Richard Callaway

Richard was born as the sixth son of Joseph (2 or Jr.). His Father, Mother and a brother died shortly thereafter of the "fever". Richard remained with the rest of his family continuing to live in the old homestead, then sold out about 1740 and settled in old Brunswick County (the portion which ultimately became Bedford County.) locating on Big Otter River at the eastern base of the Peaks of Otter. When the war broke out in 1754, the country had become considerable populated and the people collected in forts which Washington occasionally visited. Three of the Callaway brothers held the commission of Capitan: Thomas at Hickey's Fort, William at Pig River Fort and Richard at Blackwater Fort. The frontiers were constantly alarmed by marauding parties. for services in these engagements Richard and William were promoted to the rank of Bedford Militia Colonels. (This is from the account given by Lyman S. Draper in his Draper Manuscripts and is generally accepted by members of the Callaway Family.)

   Richard Callaway was born June 14, 1717, according to what purports to be the Richard Callaway Bible. Elijah Callaway, in a statement to Lyman Draper (Draper mss), said that Colonel Richard Callaway was born about 1717. Various other dates of his birth can be found in printed and manuscript mater, but the 1717 date seem to be borne out by the first appearance of Richard Callaway in official records. In 1739 he witnessed a deed of conveyance from Adolphas Hendricks to Thomas Callaway and proved the same along with Thomas Zachery on October 25, 1739 (Orange County, VA Court Orders Bk. 2, page 77). The law required that a man be of legal age, i.e. 21 years old, to witness a legal document. A mathematical deduction brings the conclusion that Richard was born "about 1717". Richard was born in Essex County, Virginia, where his Father, Joseph was a landowner. A few years later, when his orphaned brothers and sisters began their trek to the Virginia frontiers, Richard was prominently among them.
   About 1745, Richard married Frances Walton, daughter of Robert and Frances [Sherwood] Walton. As a young man, Richard was appointed Constable of Lunenburg County, Virginia on May 5, 1746 (Lunenburg Co. Court Order bk. 1, page 5). And on August 20, 1747, he patented his first land, 244 acres in Brunswick County, Virginia on the lower side of Buffalo Creek (VA Patent Bk 26, pg 101). This land, he and his wife, Frances, sold to William Callaway on March 8, 1750 (Lunenburg Co. Deed Bk 2, page 55). Also in this year, the Lunenburg tithables list showed that he had acquired a negro named Tony.
   On July 2, 1754, Richard patented 4,100 acres of land in Lunenburg Co., "on both sides of Elk Creek, the east side of Johnson's Mountain, the end of Fleming's Mountain, Buck Mountain, etc...." (VA Patent Bk. 32, page 373.) He sold most of this 4,100 acres to others over a period of years, but retained 1,000 acres for his own plantation where he live with his wife, Frances and his family. He maintained his home here until about September 1768, when he and his new wife, Elizbeth Hoy Jones, sold the tract to Peter Davie and Robert Cowan (Bedford Co. Deed Bk 3, pg 226). They then moved to a tract he had purchased from Thomas Turpin in 1765, 700 acres near the Bue Ridge Mountains adjoining Sam'l Cobb, Tuckahoe Creek and a ridge belong to John Dawson (Bedford Co. Deed Book 3, page 173). They lived on this plantation for the remainder of their years in Bedford County.
   During the last twenty years of his residency in Virginia, Richard patented and then sold large tracts of land. He patented over 9,000 acres (9,386) but we find that he purchased only two tracts, the 700 acres bought from Thomas Turpin where he resided after 1768 and lot No. 30 in the Town of New London.
   When Bedford County was created in 1754 from Lunenburg County, Richard's land fell into the new county. Immediately he was prominent in the public affairs of Bedford County. At the first court held for Bedford at the home of Matthew Talbot on May 5, 1754, Richard was among those recommended as a Justice of the peace and he took the oath of office on July 22, 1754 (Bedford Co. Court Order Bk 1-A, page 2 and Bk 1-A, page 4).
   At a court held the 26th of August 1754, Richard was appointed Surveyor of the "Road from the foot of Johnson Mountain in Callaways Road..." (Bedford Co. Court Order Bk. 1-A, page 18).
   Richard Callaway, Gentl. and Matthew Talbot were appointed to employ some people to build a Double chimney to the Prison at a court held November 27, 1754 (Bedford County Court Order Bk, 1-A, page 44). Then on November 25, 1755, Richard Callaway, Zacariah Isbell and Benjamin Howard, Gentlemen, were appointed Trustees "in behalf of this County (Bedford) for William Callaway to make a deed in fee simple for 100 acres of land in trust to them to be sold for the benefit of the sd county....and they are also empowered to lay off the said 100 acres in lotts or otherwise, etc....." (Bedford County Court Order Book 1-A, page 132). This was the creation of the town of New London, and Richard Callaway served as one of its Trustees as long as he remained in Bedford County. It is evident from these selected items from Bedford Court Orders that Richard Callaway was a prominent and active participant in the affairs of the county.
   Richard remained active in Bedford affairs for many years, being appointed to take tithable lists, to Road juries and to serve as a juror as well as sitting on the county court. At a court held September 22, 1755, he was appointed Captain of the Militia, and at the court held November 28, 1758, he took the oath as Colonel of the Bedford County Militia (Bedford County Court Order Book 1-A, Page 115 and Book 1-B, page 98).
   There is a bit of confusion among writers and the records as to Richard Callaway's status during the French and Indian War. While Hening's Statutes At Large, Vol. 7, p 204, has him listed as a Lieutenant from Bedford County in September 1758 for which he received l pound, 4 shillings, the Virginia House of burgesses made a payment to him as a Captain in 1757. This inconsistency probably reflects the slow movement of the wheels of government. In November 1758, he took the oath as Colonel of Militia for Bedford County.
   On Friday, June 3, 1757, the Virginia House of Burgesses approved payment of accounts of the Officers of the Militia of the Several Counties that were ordered out by His Honor the Governor for the Protection of the Frontiers. The Journal shows "It also appears to this Committee That the Account of Richard Callaway, Captain of a Company of Militia in Bedford County for pay to the said Company, as regulated by the Committee, including the sume of 13 pounds, 19 shillings, 8 pence to Captain Mead, in the whole amounting to 159 pounds, 10 shillings is just: That the said Callaway hath received from the Treasury the sum of 174 pounds, 5 shillings and that the Balance of 14 pounds, 15 shillings remains in his Hands to be accounted for upon settling of his further Account". (Virginia House of Burgesses 1752-1755, 1756-1758, page 484.)
   some have said that Richard Callaway commanded a fort at some period during this was, but with the absence of official evidence, one cannot state that this was a fact. Elijah Callaway wrote that Richard, William and Thomas (Callaway) served during this war and he thought "that the Blackwater Fort was assigned to Richard Callaway, the Pig River Fort to William Callaway, and Hickey's Fort to Thomas Callaway". (Draper Mss 5DD20). Perhaps it is best to say that records offer the conclusion that Richard Callaway did actively participate in some capacity during the French and Indian War.
   Late in the year 1766, soon after the birth of their daughter, Theodosia, Frances Walton Callaway died. Within the next year (1767) Richard married his second wife, Elizabeth Jones Hoy, the widow of John Hoy of Buckingham County, Virginia. She was the Mother of two sons by John Hoy, John Booker Hoy and William Hoy.
   In an article published in The Filson Club History Quarterly [volume 29, no. 1, January 1955, Louisville, Kentucky] by R. Alexander Bate A.B., M.D., "Probably no single man accomplished more than did Colonel Richard Callaway in laying the foundation that culminated in the admission of Kentucky into the Union on June 1, 1792. Yet due recognition has never been give him. Some day a historian will write the story and give Colonel Callaway his deserved credit. I am not attempting to write this story. My only desire is to call attention to this commission, and assemble in more or less chronological order bits of evidence, and point out their significance. Some ambitious student, studying for his doctorate degree would do well to take the life of Colonel Callaway as the subject of his thesis.
   In Boone's narrative of 'the Wars of Kentucke' , Colonel Richard Callaway is mentioned only once: 'On the fourteenth day of July, 1776, two of Col. Callaway's daughters and one of mine, were taken prisoners near the fort. I immediately pursued the Indians with only eight men, and on the sixteenth overtook them, killed two of the party, and recovered the girls.' From this statement one would never know that Colonel Callaway also headed a band of riflemen and gave pursuit. The story is more fully told by George W. Ranck in his "Boonesborough (Filson Club Publications: No. 16, pp 50-51). In Collins "History of Kentucky" (1924), vol. 1, page 19, it is said of the rescue - "Their fathers and friends recaptured them, uninjured, next day, thirty mile distant."
   That little or nothing was said about Colonel Callaway by Boone or Filson was due no doubt to the fact that Callaway was killed in 1780, two years before Filson came to Kentucky and four years before Filson's history was published. Filson may never have seen or heard of Colonel Callaway. Boone was intent on telling his own life's story, a case of "out of sight, out of mind," perhaps.
   Boone's fame, however, in no way lessens the importance and glory of Colonel Richard Callaway in Colonial and Kentucky history. Colonial and state records in Virginia furnish source material for Colonel Callaway's early history and his participation in the French and Indian Wars. The diaries of Colonel Richard Henderson and Colonel Daniel Trabue give important data concerning Richard Callaway's career in Kentucky. Other material is found in Collins' "History of Kentucky"; the Journal of the Proceedings of the House of Delegates, or Representatives, of the Colony of Transylvania; Acts of the General Assembly of Virginia; and the Draper Mss., Wisconsin State Historical Society. Scattered accounts of various activities of Colonel Callaway will be found in many published works, such as "Boonesborough", Filson Club Publications: No. 16, by George W. Ranck, "Annals of Tennessee" (1853), by B. G. M. Ramsey, the writings of Dr. Archibald Henderson of the University of North Carolina, and Charles W. Bryan Jr.'s article "Richard Callaway, Kentucky Pioneer," in the Filson Club History
   Quarterly, January 1935, to mention only a few.
   The Callaway family tree or chart give the birth date of Colonel Richard Callaway as 1722. He was probably born on the original grant from the Crown in Charles City County, Virginia, though Ranck says he was a native of Caroline County, Virginia. His father, mother and a brother are said to have sickened and died of a fever, within a period of weeks. The children lived at the old homestead for some years. But this property was eventually disposed of and they joined their elder brother, William, in Bedford County, Virginia.
   When Richard was eighteen years old he settled on Big Otter River, then in Brunswick County, afterwards in Lunenburg and finally in Bedford County, Virginia, at the eastern base of the noted Peaks of Otter. Lunenburg County was taken from Brunswick County in 1746. Bedford County was cut from Lunenburg County in 1755. The Callaways were the first to clear and cultivate the soil in this section.
   In 1745, or when twenty-three years old, Richard married Frances Walton of Bedford County, a sister of Thurward Walton, county surveyor who assisted the Callaways in locating land. After Frances Walton Callaway died, he married Margaret Wells of Buckingham County, Virginia. (There is some disagreement over this information. Many claim his second wife was Elizabeth Jones Hoy, widow of John Hoy - see above.) Researcher Update: It is now apparent that Margaret Wells married Richard Callaway, Jr., the son of Colonel Richard Callaway. Mrs. Elizabeth Jones Hoy was the second wife of Colonel Callaway.
   In 1754, Lt. Governor Robert Dinwiddie of Virginia sent Major George Washington, Adjutant General of the colonial militia, guided by Christopher Gist, the explorer, to remonstrate with the French. Following Washington's report William Trent, of Lexington, Virginia, built a log fort at the forks of the Ohio. Braddock's defeat was in 1755 and the French and Indian wars were being waged. They lasted from 1754 to 1763, and Richard Callaway served during this period with distinction, ultimately being promoted to the rank of colonel of the militia. Thomas and William Callaway, his brothers, were also officers in these wars. The Task of protecting three hundred and fifty miles of frontier was the task of the Virginia militia. Richard had command at Black Water Fort, Thomas at Hickey's Fort and William at Pig River Fort. Thus Richard became acquainted with and experienced in the construction and defense of outpost forts. This enabled him later to be of inestimable value at Boonesborough.
   About 1755 or shortly thereafter William Callaway founded New London in Bedford County, Virginia. Investigations by Mr. Callaway Bright disclose that Deed Book A, page 113 shows the conveyance in 1757 of fifty acres of land to Richard Callaway, et. al, as trustees to be laid off in the Town of New London; and again in 1767, Deed Book C, page 97, an additional fifty acres were conveyed to the same trustees. Other members of the Callaway family also served as trustees of New London and were members of the House of Burgesses of Virginia.
   Thus is will be seen that the Bedford County Callaways were people of birth, breeding, culture and position. Many of them are listed as graduates of William and Mary College. Their pioneer experiences in various Virginia border counties stamped them as men of ability.
   In George W. Ranck's "Boonesborough" it is said that Colonel Richard Callaway, after the French and Indian Wars, evidently moved from Virginia to the Yadkin region of North Carolina but returned to Virginia just before the Revolution. While in the Yadkin region Callaway was a neighbor and friend of Daniel Boone and it was this friendship that led to Colonel Callaways's association with the Transylvania Company and his participation in the founding of Boonesborough.
   The Transylvania Company was formed in 1774. Colonel Richard Henderson of North Carolina was the principal organizer. Associated with him were John Williams, Thomas Hart, Nathaniel Hart, James Hogg, William Johnston, John Luttrell, Daid Hart, and Leonard Henly Bullock. Dr. Archibald Henderson, of the University of North Carolina, Chapel Hill, North Carolina, has written an excellent history of this company published in three parts in Vol. 21 of The Filson Club History Quarterly (1947), entitled "The Transylvania Company, Study in Personnel." In his article, Dr. Henderson refers to Colonel Richard Callaway as "Famous in Kentucky history," citing J.G.M. Ramsy's "Annals of Tennessee: (1853)."
   The Transylvania Company was a great land company which successively bore the names of the Louisa Company, The Transylvania Company, and Richard Henderson and Company. Colonel Henderson as early as 1763 met Daniel Boone and became fascinated with Boone's tales of his wanderings in the western lands. And it was Boone who negotiated a treaty, concluded on March 17, 1775, with the Cherokee Indians, at the Sycamore Shoals on the Watauga River, and for £10,000 acquired for the land company the Cherokee claim to some 20,000,000 acres of land in Tennessee and Kentucky, preparatory to the expedition into that region. A spot had already been selected for headquarters on the Kentucky River near the mouth of what was known even then as Otter Creek, probably so named by an early hunter from the Peaks of Otter, where Colonel Callaway lived.
   In the "Annals of Kentucky" in Collins' History Vol.I, page 18, read: "February (1777)-Captain William Twetty, Samuel Coburn, James Bridges, Thomas Johnson, John Hart, William Hicks, James Peeke, and Felix Walker leave Rutherford County, North Carolina, ‘to explore a country by the name of Leowvisay,' (Louisa, or Levisa, now Kentucky). They proceed to Watawgo (Watawga) river, a tributary of the Holston, at a point now in the State of Tennessee, remaining some days, while Col. Henderson was negotiating his treaty below mentioned. Thence go the Long Island, in Holsten River, to join Colonel Daniel Boone, his brother Squire Boone, Colonel Richard Callaway, John Kennedy, and their associates-in all, 30 persons-with Daniel Boone as pilot."
   Even before the conclusion of the Watawga treaty Daniel Boone left Sycamore Shoals from Long Island and, as pilot of his associates, including Colonel Callaway, began to mark and cut out a road to the spot of their destination - Boonesborough. They were attacked by Indians twelve miles from Boonesborough and Captain Twetty was killed and Felix Walker badly wounded. Some of the men turned back, but the others pressed on.
   In the meantime Colonel Richard Henderson and his associates, with a company of about thirty men, had started to join Boone and Callaway and their associates. Colonel Henderson in his diary says:
   "Monday, March 2oth, 1775-Having finished my treaty with the Indians at Wataugah set
   out for Louisa. (This was another name attempted for the Kentucky River and its valley.)
   Saturday 25th Came to Mrs. Callaways.
   Monday 27th Employed in storing away goods."
   In Collins' "Annals of Kentucky", we read:
   "April (1775)-Colonel Richard Henderson and Colonel John Luttrell of North
   Caroline, Captain William Cooke, and Colonel Thomas Slaughter, of Virginia
   with a company of about 30 men, arrived at Boonesborough-increasing the military
   force to about 60 men."
   Thus we see Colonel Richard Callaway as an integral part of the Transylvania Company's venture.
   Upon leaving his attractive surroundings in Virginia to come to the wilderness that was to become Kentucky, he was simply continuing his habit of pioneering. By reason of his experiences in the French and Indian Wars, in constructing and defending outposts forts, in the clearance and cultivation of frontier lands, and in the settlement and founding of New London, Colonel Callaway was, perhaps, the best prepared man with the Transylvania Company for the work in hand.
   As Colonel Callaway is never spoken as a member of the Transylvania Company it may be assumed that he joined them as commander of the military escort and as consultant to Colonel Henderson in drawing the plans for the fort that was to be built. The fort at Boonesborough apparently was built upon the most approved style of the times, since it succeeded in withstanding the most terrific siege of the pioneer days. This was not the hasty lodgement thrown up on the arrival. It was a carefully planned construction. And Colonel Callaway had the experience in such matters.
   The "big fort" at Boonesborough was begun on April 22, 1775, on the south side of the Kentucky River, in what is now Madison County. Collins says it was finished on June 14, and "by compliment it is called Boonebourg or Boonesborough." Other stations or block houses were built at Harrodsburg, Boiling Springs and St. Asaph's.
   Colonel Henderson and his party arrived at Boonesborough on Thursday, April 20, 1775. In his diary her notes: "Sunday 23d passed the day without public worship as no place is provided for that purpose. Monday proceeded with the assistance of Capt. Boone & Col. Callaway in laying off lots, finished 19 besides one reserved round fine spring."
   The Transylvania Company or the Henderson Company opened a land office at Boonesborough and deeds were issued by the company as "Proprietors of the Colony of Transylvania."
   At the call of Colonel Henderson, representatives chosen by the people of Transylvania met on May 23, 1775, at Boonesborough and agreed upon, says Collins, "a proprietary government, and pass nine laws-the first legislative body west of the Allegheny and Cumberland Mountains."
   The "Journal of the Proceedings of the House of Delegates or Representatives of the Colony of Transylvania" shows that Colonel Richard Callaway was one of the six delegates elected for Boonesborough. The others were Squire Boone, Daniel Boone, William Cooke, Samuel Henderson and William Moore. Harrodsburg, Boiling Springs and St. Asaph's were also represented.
   As Proprietor of the Transylvania Company, Colonel Richard Henderson opened the convention with a speech. Colonel Callaway and four others were appointed as a committee to draw up an answer to the proprietor's speech. Later, on May 25, 1777, Colonel Callaway was appointed on a committee to draft and introduce a bill for the establishment of Courts of Justices and regulating the practice therein. And on May 27, 1775, Colonel Callaway was "ordered" to "wait on the proprietors with the laws that have passed."


-------------------- Sergeant, Lt.,Maj. in the Indian wars. Col. Calloway was commandant of Ft. Boonsborough. He was killed and scalped by Shawnee Indians just a mile or so up the river while attempting to construct the area's first ferry. He was married twice : (1) Frances Walton, and (2) Mrs. Elizabeth Hoy.Re. Society of Boonsborough, P.O. Box 226, Richmond, Ky. 40476-0226.

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Col Richard Callaway's Timeline

June 14, 1717
Madison, Kentucky, United States
May 7, 1741
Age 23
July 1745
Age 28
September 4, 1750
Age 33
Age 34
Bedford, Virginia, United States
Age 36
Bedford County, Virginia, United States
June 5, 1756
Age 38
Bedford County, Virginia, United States
September 1758
Age 41
August 14, 1760
Age 43
August 9, 1762
Age 45