The Calloway Family Of Virginia

Not much is known about Joseph CALLAWAY Sr.  He had at least one child: 

+ 2. i. Joseph CALLAWAY Jr. 

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Generation Two

2. Joseph CALLAWAY Jr. (Joseph)His wife is unknown. He died in 1732 in Essex County, Virginia.1

Children of Joseph CALLAWAY Jr. were: 

1. John CALLAWAY. 
2. Capt. Thomas CALLAWAY Sr., born 12 Oct 1712; married Sarah    May (Mary) BAKER. 
3. Francis CALLAWAY, born circa 1716 in Essex County, Virginia. 
5. Col. Richard CALLAWAY, born 14 Jun 1717 in Essex County, Virginia. 
6. James C. CALLAWAY, married Sarah BRAMLETT. 
7. Elizabeth CALLAWAY. 
8. Joseph Callaway, born 1741 Bedford Va. Married Polly Barrett

William Calloway Of Bedford Co. Virginia

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4.--- Capt. Thomas CALLAWAY Sr. (Joseph, Joseph) was born on 12 Oct 1712. He married Sarah May BAKER in 1735. He died in Feb 1800 in Ashe County, North Carolina, at age 87. He was buried in Callaway Cemetery, West Jefferson, Ashe County, North Carolina. His brothers moved into what is now Bedford County, Virginia in the mid 18th Century, but Thomas did not, living instead in Halifax and Pittsylvania Counties before moving to the New River in what then was Surry County, North Carolina, it later became Wilkes County, and now is Ashe County. He and some of his sons had moved to the Greenville and Pendleton Districts of South Carolina by 1790, but some of them had returned to Wilkes County by 1796. One source states that he was born in 1700 and lived to age 100.

From The Callaway Journal, vol. 1 (1976), p. 25: "It is told that Capt. Thomas [Callaway] and Daniel Boone were quite good friends and one day, while hunting near Calloway's home, Boone killed a deer. The deer fell across a long gray stone which Boone set up against a chestnut tree. Later, Capt. Calloway saw the stone and was so fascinated with it that Boone brought it to his home and carved upon it the initials, 'T.C.' So pleased was he that Calloway wanted it for a headstone at his grave, and there it was erected upon his death in 1800." In 1755 he was a captain in the Colonial Troops from Halifax County, Virginia in the French and Indian War, and in 1780 he and some of his sons participated in the Battle of Kings Mountain in the American Revolution

May (Mary)1 Baker (RobertA, JohnB, Andrew "Andy"C, GeorgeD, ChristopherE, JohnF, SimonG) was born Abt. 1703 in Wilkes Co, NC, and died February 1800 in Walnut Grove, Ashe County, NC. She married Capt. Thomas Callaway. He was born October 12, 1700 in Caroline, VA, and died 1800 in Walnut Grove, Ashe County, NC. Mary BAKER was daughter of Robert Baker of Ashe Co. N.C. She left a will mentioning her nephew Richard Baker.

In the Draper Manuscripts on micro-film (roll 12, series DD, item #51)There is a letter from Dr. James Calloway (son of Elijah and gr.son of Thomas) to Lyman C. Draper dated Aug. 1845. Dr. James C. Calloway says "Capt. Thos. Calloway married about the year 1735, Mary Baker, in N.C. Mary Baker was aunt of Rev. Andrew Baker.

Children of Capt. Thomas CALLAWAY Sr. and Mary BAKER were: 

10. i. Charles CALLAWAY married _____ _____. He was born before 1746. He died after 1810 in Burke County,
 North Carolina. 
11. ii. James CALLAWAY was born before 1746. He died before 1810. 
12. iii. Richard CALLAWAY was born before 1746. He died on 5 Mar 1819 in Ashe County, North Carolina.
 He had no children. 
13. iv. Elizabeth CALLAWAY married Littleberry (Berry)Toney.  
 14. v. Thomas CALLAWAY Jr., born 1753 in Halifax County, Virginia; married Jude Ann _____. 
15. vi. William CALLAWAY was born before 1755. He died after 1800. He appears to have moved to South
 Carolina by 1790.11 
 16. vii. Joseph CALLAWAY, born after 1755; married Polly BARRETT. 
 17. viii. Frances CALLAWAY, born circa 1758 in Halifax County, Virginia. 

Calloways in the Battle of Kings Mounatain

The Battle of Kings Mountain was a famous Revolutionary war battle fought in the Wilkes, Ashe, and Surry areas of North Carolina. The Callaway men played an important part in Colonel Benjamin Cleveland’s Kings Mountain Campaign. Thomas Callaway, his sons, and his sons-in-law, were important to this campaign. The Callaways and the Clevelands were very good friends. To Colonel Cleveland, whose career replete with perilous adventures, an occurrence now transpired, which at one time threatened the most tragic termination: and which, for its hair-breadth escapes, may be regarded as the most notable event of his life. (Lyman Draper).

Cleveland lived near Wilkesboro, North Carolina. He owned property thirty-five miles away. It was near the round-about on the Yadkin River and close by the South bank of the New River. It was known as The Old Fields. While he was visiting his New River plantation, unfortunately, William Riddle, a noted Tory leader was approaching from the Virginia border. The British had a reward out for Whigs (rebels) and Riddle knew it. First, he caused trouble by stopping by the home of Benjamin Cutbirth, an old friend to Daniel Boone. He could get no information from Cutbirth, so, he started quizzing their women. They found out that Cleveland was a short distance away.

There happened to be some of the Callaway family present when he questioned the women. Every Tory in the area knew of Cleveland’s hatred of their race and how prominently he figured at Kings Mountain. Cleveland had been responsible for the hanging of many Tories; capturing him would be no small honor. Since Riddle only had a small company with him, he had to resort to stratagem. He decided to steal Cleveland’s horses in the quiet of the night. He supposed that Cleveland would follow the trail of the horses the next morning. The horses were taken to a place just above the Perkin’s house, then Riddle and company waited.

During Saturday, Richard Callaway and his brother-in-law, John Shirley, went down from the neighboring residence of Thomas Callaway to Duncan’s, to see Colonel Cleveland. The next morning Callaway, Duncan, and Shirley helped him track the horses. When they reached the Perkin’s place, they were told of the ambuscade (ambush). Callway and Shirley kept Cleveland behind them. But one of Riddle’s bullets struck Callaway, Duncan and Shirley escaped. Unfortunately, Cleveland, weighing fully three hundred pounds knew he could not outrun them, he was doomed. They pledged to spare his life if he surrendered. Don’t know where she came from, but Cleveland grabbed a woman named Abigail Walters and used her as a puppet, keeping her between him and the would-be assassins. Seeing that the woman was terrified, and that Riddle and Wells would shoot her too, Cleveland gave himself up (Draper’s Manuscripts). They camped for the night at a place called Riddle’s Knob in Watauga County, close to where Cleveland was captured.

Early on the Sabbath morning, Joseph Callaway and his brother-in-law Berry Toney, wishing to see Colonel Cleveland on a business matter, called at Duncan’s. They soon learned about the missing horses and the ambuscade. They met Duncan and Shirley in rapid flight, and were told that Richard Callaway had fallen. They were told that Colonel Cleveland was either killed or taken. It was decided that Duncan, Shirley, and Toney would notify people in the scattered settlements to meet at the Old fields. Joseph Callaway went to his father’s house and mounted his horse; then he hastened to tell Colonel Cleveland’s brother Captain Robert Cleveland. Joseph’s brother William Callaway started forthwith up the river, and soon joined Samuel McQueen and Benjamin Greer. They followed the trail as best they could until night fell. They were now about ten miles from the Old Fields. William Callaway suggested that McQueen remain there, while Greer gathered up more men to pursue the Tories. By nightfall, Cleveland’s brother and friends, and those who had served under him, had gathered at Old Fields determined to rescue their old commander at every hazard. They trailed Riddle’s party to the gates of Old Ninety Six. A little after sunrise, the Callway party discovered Riddle’s camp. They crept along the trail, with only nine men close enough to attack Riddle’s camp. Colonel Cleveland was sitting on a large fallen tree, engaged under compulsion, in writing passes for the several members of Captain Riddle’s party, certifying that each was a good Whig. These were to be used in a tight spot, to help them out of difficulty. Cleveland was taking his time and making some blunders; he had a feeling that when these were readied, his usefulness would be served.

In the next moment guns were fired and the Whigs rushed up. Colonel Cleveland rolled off the log and to the ground to protect himself. While scampering away, Wells was shot by William Callaway. Callaway’s men took hot pursuit of the remainder of Riddle’s men. Well, Cleveland was rescued , and William Callaway was overjoyed the he had shot wells, who had so badly wounded his brother Richard. So, this is how the Callaway and kin rescued Colonel Cleveland from the Tories clutches.