I lifted this from a Calloway website. Maybe someone can use it. I have not studied this line very much. Capt. Christopher Irvine (a cousin? to my orphan Christopher) married Lydia Calloway, daughter of Richard. Capt. Irvine was killed by Indians in 1786 in Ohio territory. The mentioned Draper Papers are a genealogical goldmine. Getting access to the entire work is difficult. Edwin In 1838 Lyman C. Draper became very concerned about the alarming number of romanticized and highly fanciful narratives that were beginning to appear about the early American pioneers, so he began writing letters to, and personally interviewing the survivors of these early pioneer days in an attempt to learn the facts. Over the next 53 years he compiled notes and letters that now amount to over 500 volumes that are on file in the State Historical Society of Wisconsin. Among these records are a number of letters exchanged between Lyman C. Draper and Dr. James Calloway (son of Elijah Calloway and grandson of Thomas Calloway), and earlier letters to Draper from Elijah Calloway. [Note: in one of these letters Dr. James Calloway says that all of his early ancestors spelled the name Callaway with an "a" in the second sylable but now they all spell it Calloway with an "o". ] My abstracts of these letters with my notes in [brackets]: Letter from Dr. James Calloway to Draper. August 1845. Col. James Calloway is of Bedford and was the oldest son of Capt. Wm. Calloway. Nephew of Col. Richard Calloway.Richard Calloway was seriously wounded at the capture of Col. Cleveland and left on the ground by the Tories ... he lived many years and died in Tenn. in the year 1822. Mentions John Shirley brother-in-law of Richard Calloway. . . Thos. Calloway married about the year 1735, Mary Baker in N.C. She was aunt of Rev. Andrew Baker.[Richard Calloway who was wounded at the capture of Col. Cleveland and brother-in-law of John Shirley is a son of Thomas Calloway. Col. Richard Calloway was a brother of Thomas Calloway.] Lyman C. Draper Questionaire for James Callaway and his replies. Berry Toney was brother-in-law of Richard Calloway and was present when he was wounded at the Old Fields. Married the sister of Richard Calloway. John Shirley also brother-in-law of Rich Calloway, married his sister.[This Richard is the son of Thomas Calloway, not his brother.] Letter from James Calloway to Draper. Wilkesboro, N.C. Feb. 21, 1846. Says he remembers his father, mother, and grandmother Calloway telling of the trip his grandfather Cutbirth made to the Mississippi River and New Orleans about 1760 ... at the time he[Cutbirth] lived in the forks of the Yadkin, Rowan Co., N.C. Names grandmother Cutbirth's sons Daniel and Benjamin and daughters Seary (SP?) and Sally. . .All of his ancestors originally spelled the family name Callaway but now all spell it Calloway with an "o". . . Sarah Calloway captured by Indians . . .Samuel Henderson married Sarah Calloway, daughter of Col. Richard Calloway. [There is some conflict here. Most sources, including other letters in the Draper Manuscripts say that the daughters of Col. Richard Calloway who were captured along with Daniel Boone's daughter, Jemima, were Francis and Elizabeth and that Elizabeth Calloway married Samuel Henderson and this is verified by letters to Draper from their son ] Letter from James Calloway to Draper. Feb. 19, 1852. Note at top apparently in Draper's hand says "Death of Elijah Calloway". "My father died the 3rd day of March 1847. He was born the 12th day of Nov. 1769." Letter mentions his brother Josepth W. Calloway. Most of this letter was devoted to the location of Daniel Boone's home on the Yadkin in Wilkes Co., NC. He then answers Draper's questions about relationship to Cutbirth family and Daniel Boone. Says his grandfather was Benjamin Cutbirth. His great grandmother was the sister of Col. Daniel Boone and wife of John Wilcoxin. His grandmother's name was Elizabeth. [Sarah Cassandra Boone, sister of Daniel Boone, married John Wilcoxin. Their daughter Elizabeth Wilcoxin married Benjamin Cutbirth. Their daughter Mary Cutbirth married Elijah Callaway, son of Thomas Callaway and father of the writer, James Calloway.] On June 10, 1845 Elijah Calloway sent a 20+ page history on Col. Richard Calloway to Lyman C. Draper. Perhaps there are better copies available but much of this is unreadable on the micro-filmed copy I have studied. Some pages were completely unreadable and as much had no genealogy value I have only transcribed what I could that has genealogy value: Col. Richard Calloway. The Hero of ___ Kentucky who was killed by the Indians in the early settlements of that Country was Born in the County of Caroline State of Virginia about the year 1717 his grandfather Joseph Callaway imigrated from England among the first settlers in Virginia Who had one son by the name of Joseph and who settled at the place where Richard was born, when it was a frontieer wilderness, Where he lived and had seven sons and two daughters. His eldest son Thomas the authors Father was born Oct. the 12th 1700. 2nd son Joseph, William, Francis, John, Richard, and James his Two Daughters, Nancy and Seneath. Richard's Father and Mother and Joseph all died with the feaver in a ____ Six weeks leaving a large house full of Children where they all lived together until they were nearly grown. They being an enterprising set of young men and finding that tract of land being two small to be Divided among them all They mutally consented to sell off that Land and move to the west in quest of gitting more and better land. They sold off and started about the year 1738 to the frontier of Virginia and settled on Big Otter River in the frontier of Bedford County and was the first white men that cut the first stick of Timber to make corn on Big Otter River, and they being enterprising men they ____ a great deal of land and as Richard is to be the principal man of this memorial, He was shortly afterwards married to the Daughter of George Walton who was a near relation to _____ Walton who helped to ____ the day with Co. Cleveland on Noby Chuckey (SP?) River --- and as Richard's wife was an older Sister to Sherwood Walton who was ____ surveryor of Bedford County it enabled Richard and all the rest of his Brothers to to _____ a ____ of land so that most of them got very rich, and some went to farming and some to Merchandizing. The Author's Father, Thomas Calloway, took up the business that was then called Indian Trader by which Practice he took great quantity of goods and a number of horses frontieers Letters among the white people and the Indians and recieved in the exchange Furs and peltry of all kinds. But as the Indians was frequently troublesome on the frontieer by killing and driving off people's stock it became nessary that the militia should be trained and Dissiflea and kept in readiness, and as the Calloways were throughing and _____ _____ men, Richard, Thomas, and William was all appointed ____ Capts for to raise and train and keep in _____ Three companies of Volunteers to repell any hostilities as the Indians were was obligesed to be kept in check. About the year 1753 when the Indians _______ very troublesome being set only the Canadain the Capts Richard Calloway, William Calloway and Thomas Calloway the authors father with their volunteer companies was called in to active service as the Indians began to butcher the ______ on all sides and war being declared between Great Brittan and France _____________The Author thinks that the Black water fort was assigned to Richard Calloway the Pig River fort to William Calloway and Hickeys fort to Thomas Calloway. . . [at this point the letter goes into great detail about the French and Indian war but contains no genealogy data] . . . The war being ended the Calloways returned to their private consernes. Richard Calloway soone rose to the Col. Commandant of Bedford County which office he held until he left that County. Col. Daniel Boone having discovered the vast rich body of land in Kentucky and Calloway being _____ of a great land speculator he determined to move to it and selling off most of his lands in Virginia and about the year 75 he moved with his whole family to Boones Station in Kentucky. Edwin's note: There is much speculation that Jemima Boone was actually the daughter of Daniel Boone's brother. The old story goes that Daniel was on one of his adventures in the Carolinas, and his wife had given him up for dead. Much of the stuff written about Boone is a fairy tale, so draw your own conclusions.