Callaway of Virginia and Kentucky

Joseph Callaway emigrated from England to Virginia and his son, Joseph Callaway, Jr. settled in Caroline County, Virginia where he had seven sons and two daughters.

Richard Callaway was the sixth son. While Richard was young, his parents died. In 1740 the family sold their homestead in Caroline County, removing to Brunswick County in that portion which ultimately became Bedford County. Their home was located on the Big Otter River at the eastern base of the Peaks of Otter. When the Indian War of 1754 broke out, three of the Callaway brothers held the commission of captain. Thomas Callway at Hickey's Fort; William Callaway at Pig River Fort; and Richard Callaway at Blackwater Fort. For their service, Richard and William were promotion to Colonels in the Bedford Militia. Issue of Richard Callaway:

Thomas Callaway, born 1712, removed from Spotsylvania County to Halifax County where he was appointed constable in 1738 of the upper precincts of the James river mountains. In 1758 he received pay for service as an Ensign in the Augusta County Militia; afters as captain of a Halifax County.
William Callaway, born 1714 married (1) in 1735 Elizabeth Tilley by whom he had five children, viz:
1. James Callaway, born 1736, married three times; resided in Bedford County where he died in 1809.
2. John Callaway, born 1738, married (1) Tabitha, daughter of Henry and Sarah Tate (2) Agatha, daughter of John Ward.
3. William Callaway, Jr., born 1740 married Anne Bowker Smith, resided in Bedford County.
4. Elizabeth Callaway, born 1743, married Captain Francis Thorp of Campbell County.
5. Mary Campbell, born 1746, married Jacob Anderson of Campbell County.
6. Charles Callaway, married in 1768 to Mrs. Judith Pate nee Early, widow of John Pate, resided in Campbell County.
Francis Callaway, born 1716, removed to Wilkes County, Georgia.
James Callaway, planter in Spotsylvania County.
Richard Callaway, born 1719, patented lands in Brunswick and Lunenburg Counties from 1747 to 1754; served as a sergeant, lieutenant and major of forces active in the French and Indian wars. He was married to Frances, a daughter of George Walton, of Bedford County. In 1761 Richard Callaway was appointed one of the trustees of New London; he patented lands in Bedford County from 1762 to 1770; visited North Carolina and Kentucky; went with Daniel Boone into Kentucky and assisted him in the founding of Boonesboro, where he ultimately settled. In 1776 when his two daughters and Jemima Boone were captured by Indians, he led a company in pursuit. He was elected burgess to the Virginia Assembly from Kentucky in 1777; appointed to a commission for opening a road over the Cumberland Mountains into Kentucky in 1779. On 8 March of 1780 while Callaway and several others were engated constructing a ferry boat, they were fired on by the Shawanese Indians and Callaway was killed and scalped. Two days later his body was recovered and buried behind the fort. He left a widow and children from both marriages.