
Captivating Tales of Caintuck
- Who Was Flanders Callaway?

George Caleb “Bingham’s Daniel Boone Escorting Settlers through Cumberland Gap”
Bingham erroneously showed Flanders Callaway to Boone’s right as an old man. Flanders was only 22 years of age when he entered Kentucky.At a recent fall festival, I spoke with a man about Jemima Boone when he showed an interest in my book Caintuck Lies Within My Soul. He said, “I cannot figure out why Daniel let Jemima marry Flanders Callaway since his father and Daniel hated each other.” Isn’t it strange how history sometimes confuses players in events, giving them relationships that carry forth into books and documents for years and years?
Being a historian and author, I had to explain his misconception, for Flanders was not Richard Callaway’s son. In Caintuck, the reader learns a more accurate lineage for this young man at his introduction into my story.
Flanders Isham Callaway, Richard’s twenty-two-year-old nephew and his younger brothers, James and Micajah, had traveled to Caintuck with our party despite their families’ strong objections. Their father, James, had passed many years earlier, and their mother, Sarah, only two years earlier.
Flanders’ father James had died in 1767 and his mother Sarah, nee Bramlett, had passed sometime after November of 1773. Flanders had at least five brothers and three sisters, all born in Virginia. His brothers, James and Micajah, would be among those captured at the salt lick (Blue or Big Bone?—an argument for another post) in February of 1778. Each was held captive for several years.
Flanders was not captured as he had been tasked with furnishing meat for the party of salt boilers and was not in camp when the Shawnee took the men. He and his hunting companion arrived to find the camp in disarray.
Jemima and Flanders married and had ten children, six girls and four boys. Flanders died in Missouri on 22 Feb 1829. He was 76 years old.
- A Boone Son – James

Early September 1773, sixteen-year-old James Boone stood ready to follow his well-known father on yet another adventure. This time, he would go along—be part of an expedition into the wilderness they called Caintuck. Some forty individuals planned to make the trip including his immediate family, his father, Daniel, age 39, his 34-year-old mother, Rebecca, and seven younger siblings: Israel, age 14, Susannah, age 12, Jemima, age 10, Levina, age 7, Rebecca, age 5, Daniel Morgan, age 3, and baby Jesse, only three months old.
They would cross three mountain ranges between their current home near Moore’s Fort on Virginia’s Clinch River. There were rivers to ford, unforeseen dangers, and the trials of frontier travel. Not long after the journey began, Daniel sent James back to Captain William Russell’s home—a man who planned to join the expedition and later to send for his family—for more supplies, including flour and additional farming tools. The Mendinall (or Mendenhall) brothers, John and Richard, who traveled without their families, accompanied James on his errand. On his return with the supplies, Henry Russell, William’s seventeen-year-old son, Isaac Crabtree, a man named Drake, and two of the Russell family slaves, Adam and Charles, came along.
On 10 October 1773, disaster befell their small party, while camped only three miles from the Boone expedition. The Mendinall brothers died first. One slave escaped and hid nearby. He watched as James and Henry were first shot through the hips so they could not flee and then tortured for hours by Shawnee and Cherokee warriors. Isaac Crabtree was wounded, but escaped. Drake was wounded. His body was found years later. The other slave, Charles, escaped or was taken prisoner, according to which version you wish to believe.
The Boone expedition turned back. Captain Russell never again attempted to move to Kentucky. Newspapers across the region told the story in all its gory details. The story mentioned only Henry Russell by name, for his father was well known.
- Lt. Colonel Nathan Boone’s remarkable remembrances

Nathan Boone, Daniel and Rebecca’s youngest son, was born 3 March 1781, at Boone’s Station, Kentucky. Nathan came along almost six years after the loss of William, born in Virginia only days before the family made their fateful move to Kentucky in 1775. (William died days after his birth and his grave lies lost and forgotten.) Rebecca was forty-two at Nathan’s birth. Her two oldest daughters had children of their own. Susannah had her third that same year, and Jemima, her first in 1779.
Nathan is most likely the only one of all the Boone children to learn to read and write. Late in his life, Nathan gave Kentuckians and historians, personal, factual memories of his father through interviews with Lyman Draper in 1851. Draper made over 300 pages of handwritten notes, after Nathan had answered seventeen questions sent prior to Draper’s visit. Available in “My Father, Daniel Boone: The Draper Interviews with Nathan Boone”* Nathan’s words provide historians and Boone admirers with a firsthand account of a remarkable man.
Nathan himself was no slouch! He served in the War of 1812, joined the 1st United Sates Regiment of Dragoons as a captain on 2 March 1833 and rose to the rank of lieutenant colonel. Nathan and Olive Van Bibber had fourteen children. A tale for another day just might be one of their marriage and unusual honeymoon!
*Edited by Neal O. HammonIllustration: Nathan Boone’s home in Defiance, Missouri
- Susannah Boone Hays – second white woman in Kentucky?

In Caintuck Lies Within My Soul, I wrote a scene where Jemima cares for her older, pregnant sister, Suzy, after her husband beat her. Like most every incident in the book, this one is based upon fact. Susannah Boone, born 2 November 1760, suffered abuse at the hands of her husband William Hays throughout their marriage.
William Hays (1754-1804), an educated Irishman, trained as a weaver, first encountered the attractive, flirtatious, oldest Boone daughter at Moore’s Fort during Lord Dunmore’s war, in the autumn of 1774. Tasked with helping Daniel with his accounts and reports as he served as a lieutenant in the Virginia Militia, Will became a frequent visitor to the Boone’s small cabin. In early spring 1775, Suzy and Will married.
At the time of their wedding, Daniel was recruiting men for the building of Boone’s Trace, the road into Caintuck. Will Hays signed up, no doubt for the ten pounds offered for his labor. Susannah convinced her new husband and father to take her along to cook and care for the company of men. Suzy and one female slave made the arduous trip into the new lands. They skinned and cleaned game, cooked, and took care of all the “women’s work for some 25 to 30 men. Additionally, they walked into this new territory. Suzy, when told her father had named Rebecca and Jemima as the first white women in Caintuck responded, “Every Kentuckian ought to try my gait, since I was the first white women in Kentucky.” (Actually, all three had been preceded by Mary Draper Ingles, who escaped her Shawnee captors in 1755 at Big Bone Lick, Kentucky. That is a story for another day.)
Suzy bore ten children, five boys and five girls, including Elizabeth, born at Boonesborough in1776, who may have been the first white female child born in Kentucky. Suzy suffered throughout their marriage until her death on 19 October 1800, shortly after the family’s arrival in Femme Osage, Missouri. Will followed her in death only four years later, shot to death while in a drunken rage by his own son-in-law.
Illustration – 1774 The Wilderness Road by Carl Rakeman, courtesy of the Federal Highway Administration – incorrectly dated.
- The Birth of Jemima Boone – 4 October 1762

Rebecca Boone welcomed her second daughter, her fourth child, into the world on 4 October 1762. Daniel had removed his family from their North Carolina Yadkin Valley home in 1760, taking them all the way to Culpepper, Virginia, due to hostilities between the colonists and the Cherokee, During the next two years, Rebecca often lived alone except for their three small children while Daniel hunted in the mountains to the west or served in the North Carolina militia. Some of Daniel’s family had relocated nearby and provided aid when needed. Daniel and Rebecca’s three older children were James, age 5, Israel, age 3, and Susan age almost 2.
Some say Daniel had been absent from the family for 24 months before Jemima’s birth. Others point out that the treaty with the Cherokee was signed at the Long Island of the Holston on 19 November 1761. Many historians say Daniel returned to his family at this time and moved them back to Sugartree Creek, their Yadkin Valley home. Jemima always claimed she was born in North Carolina. Almost every Boone biographer has a theory as to Jemima’s true father.
Many biographers have pointed out Jemima seems to have been favored among Daniel’s offspring. Perhaps because she was the one he was able to save from hostile hands, having lost James in 1773. Perhaps because, only Jemima out of Daniel’s eight surviving children stayed in Kentucky after Daniel’s capture by the Shawnee in 1778, believing him alive and waiting for his return. Even his two oldest, Israel and Suzy had returned with Rebecca to North Carolina.
Many have documented Jemima’s promise to always stay with her father after he rescued her and the Callaway girls in 1776. Throughout her life, Jemima lived close to her father, following him across Kentucky, and then into the Missouri territory in 1799.
Jemima died on 30 August 1834 in Warren County, Missouri. She was 72 years old. She and Flanders had raised ten children to maturity. Today, she is recognized as a hero of the American Revolutionary War and the Siege of Boonesborough.
Note: There are photographs on Ancestry and other such genealogical sites purported to be Jemima and Flanders with members of their family. However, it wasn’t until 1839 that Louis Daguerre invented a process (called after him-the daguerreotype), which used silver-plated sheets of copper to make detailed permanent photographs. Jemima had been dead 5 years by then.
Image by Shari Knaust.
C. M. Huddleston:
Historian, author, professional archeologist, educator, Kentucky native
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C.M. Huddleston is the author or co-author of sixteen books. All deal with some aspect of American history. Five focus on President Theodore Roosevelt’s maternal ancestors. Four are award-winning middle-grade time-travel novels featuring Greg and Rose, who investigate and explore our country’s history, while having adventures of their own.
You can find more information on her books at
www.cmhuddleston.com.
