Richard Callaway (ca. 1717–ca. 8 March 1780), a founder of Boonesborough, Kentucky, was born in the northwestern portion of Essex County that in 1728 became Caroline County. His father was Joseph Callaway, son of an immigrant of the same name, but the name of his mother is unknown. About 1738, a few years after the deaths of their parents, Richard Callaway and several of his brothers ventured westward. They were among the first white men to farm in the vicinity of Big Otter Creek in the section of Lunenburg County that in 1753 became Bedford County. Callaway's brother William Callaway is regarded as one of the founders of the new county, and his nephew James Callaway became an important iron manufacturer during the American Revolution.
Richard Callaway became surveyor of Lunenburg County in April 1751. To obtain the position one needed a license from the College of William and Mary, a circumstance that may account for an undocumented tradition that he attended the college. Callaway also served as a constable in Lunenburg County and began acquiring land, perhaps as much as 9,000 acres in all. When Bedford County was created out of Lunenburg County he became a justice of the peace, and he served as a trustee of and perhaps surveyed the site for the county seat, later the town of New London. In July 1745 Callaway married Frances Walton, whose brother later became the surveyor of Bedford County, a connection that may have helped in his acquisition of property. Callaway had at least four sons and six or seven daughters before his wife died, probably early in the 1760s. By September 1768 he had married a widow, Elizabeth Jones Hoy. They had several more children, perhaps as many as two sons and two daughters. The Callaway brothers were active militia officers during the French and Indian War, and according to family tradition Richard Callaway and two of his brothers commanded three of Virginia's frontier forts.
Callaway sold or otherwise lost most of his land and property by the end of 1774. Financial difficulties, his family's venturesome tradition, or connections in North Carolina, where Richard Henderson's expedition to establish a new colony in Kentucky was assembling, impelled Callaway in March 1775 to join the march west. Led by Daniel Boone, Callaway and others marked the Wilderness Road to the new settlement of Boonesborough. Callaway helped lay off town lots, lived in a cabin there, conducted a large party, including his family, to the settlement, and then raised crops and livestock nearby. Claiming 3,000 acres of land, he was a justice of the peace, served in the short-lived Transylvania assembly, and was author of its judiciary statute.
Henderson's colonial experiment collapsed at the beginning of the American Revolution, and Virginia created Kentucky County in December 1776. Callaway was a justice of the peace for the new county and in June 1777 was appointed a colonel in the militia. By the end of the decade he claimed as much as 6,000 acres of Kentucky land. Callaway was elected to the House of Delegates in 1777 and again in 1779. During his first term he served on the Committee of Public Claims, and during his second he presented petitions to authorize a ferry across the Kentucky River and to create the town of Boonesborough. Callaway and Boone were appointed trustees of the new town, although apparently neither served.
In the summer of 1776 daughters of Boone and Callaway wandered away from the safety of the Boonesborough stockade and fell into the hands of the Indians. Callaway and Boone each led search parties; Boone's group recovered the girls. Callaway's relationship with Boone eventually became strained, perhaps as a consequence of Boone's early celebrity but perhaps, too, as a product of inevitable conflicts resulting from their holding similar offices and shouldering similar responsibilities without a clear priority of rank. When the town came under siege in 1778, Callaway resisted with ferocity and ingenuity and perhaps helped to construct a makeshift cannon. Boone's conduct produced allegations that he had been in collusion with the British and the Indians, and Callaway had him court-martialed. When Boone was acquitted and promoted, Callaway became bitter.
About 8 March 1780 while building a town ferryboat, Richard Callaway and at least one companion were killed by Indians near Boonesborough. His body was buried in an unmarked grave near the fort. Kentucky's Calloway County, using a variant spelling, was named in his honor in 1822.
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The complicated and incomplete record is confused by conflicting texts (Callaway Family File, Kentucky Historical Society, Frankfort; Callaway family Bible records, Library of Virginia) derived in turn from a family Bible that might have been Richard Callaway's or his namesake son's (Joseph A. Callaway, "Colonel Richard Callaway's Family Bible," Callaway Journal 6 [1981]: 28–29); biography by nephew Elijah Callaway (1845), Lyman C. Draper Papers (Draper MSS), 5DD20–44, Wisconsin Historical Society, Madison, Wis.; the most judicious and best-documented assessments are Mrs. A. E. Hart, "The Callaway Family of Virginia and Some Kentucky Descendants" (1929 typescript), LC, and Sherrill Williams, "Colonel Richard Callaway of Virginia and Kentucky," Callaway Journal 6 (1981): 75–89, which plausibly suggests 1717 birth year; less reliable biographies are Charles W. Bryan Jr., "Richard Callaway, Kentucky Pioneer," Filson Club History Quarterly 9 (1935): 35–50, and R. Alexander Bate, "Colonel Richard Callaway, 1722–1780," ibid. 29 (1955): 3–20, 166–178; many original records and references in Kentucky Series, Draper MSS; other documents printed in George W. Ranck, Boonesborough: Its Founding, Pioneer Struggles, Indian Experiences, Transylvania Days, and Revolutionary Annals (1901); death described as of Mar. 1780 in John David Shane, ed., "The Henderson Company Ledger," Filson Club History Quarterly 21 (1947): 27, 33; family Bible gives erroneous death date of 8 Mar. 1778; undocumented death date of 8 Mar. 1780 in Lyman C. Draper, The Life of Daniel Boone, ed. Ted Franklin Belue (1998), 558.