250 years ago Dolly, a woman enslaved to the Callaway family of North Carolina, was preparing to embark on an expedition that would become a cornerstone in the history of Kentucky. Months later, her son Frederick was born - the first child born at Fort Boonesborough. Frederick led a long life from enslavement to manumission to freedom, finally settling his family in northern Ohio. Though this family was enmeshed in a critical chapter of American Westward expansion through force, intimidation, and human slavery, their story ultimately reveals a spirit of resilience, ingenuity, and groundbreaking choices of self-determination.
In early March of 1775, investors in the Transylvania Company were readying for an upcoming gathering with the chiefs and members of the Overhill Cherokee Nation at the Sycamore Shoals of the Watauga River, in what is now northeastern Tennessee. When Judge Richard Henderson formed this land speculation company with fellow members John Williams, Thomas Hart, Nathaniel Hart, David Hart, John Luttrell, Leonard H. Bullock, James Hogg, and William Johnson, the intention was to establish claims on land not yet controlled by the British Crown. In defiance of the Royal Proclamation of 1763, the ultimate ambition of these investors was to create the fourteenth colony by obtaining 20 million acres of land from the Cherokee in order to sell lots to white settlers. Despite the objection of Chief Dragging Canoe, by March 17, 1775, Henderson’s enterprise acquired the indigenous peoples’ ancestral hunting ground between the Kentucky, Ohio, and Cumberland Rivers in exchange for cash and trade goods.
Months earlier, Henderson hired explorer Daniel Boone to lay the groundwork for the treaty negotiations with the Cherokee people. Immediately after the treaty was signed, Boone led a team of trailblazers north through the Cumberland Gap and up the Wilderness Trace to establish a settlement for Henderson’s company.
Other ambitious settlers accompanied Boone on this journey, including his Yadkin Valley neighbor, Colonel Richard Callaway, who brought an enslaved woman named Dolly. As one of only two women on this expedition party, Dolly played a vital role in preparing meals, tending fires, and scraping fresh hides during the arduous journey and ultimately in helping to build the new settlement on the Kentucky River. Fort Boonesborough was established on June 14th and deeds were issued by the Proprietors of the Colony of Transylvania. That September the wives, children, and enslaved moved into cabins within the fort. In November 1775, Dolly gave birth to a mixed-race son named Frederick.
In June of 1841, Orlando Brown, then the editor of the Frankfort Commonwealth, would recount:
“The first child born in Kentucky was born in Boonesborough and is now living in the family of the Editor of the Commonwealth. He is a yellow man, the child of a servant who came out as a cook for Col. Hart’s Company. We expect to be at the Harrodsburg celebration, and Old Frederick will appear in the capacity of our carriage driver. On looking at him, so full of life and vigor as he is, once can scarcely realize the fact that he is the first born in a State teeming with so many inhabitants as now fill the Dark and Bloody ground.” [1]
Dolly was separated from Frederick when he was likely sold to Captain Nathaniel Hart Sr., Callaway’s friend, fellow expeditioner, and an investor in the Transylvania Company. Though Hart lived in Callaway’s cabin at Fort Boonesborough, he spent most of his time overseeing the clearing and planting of land and building of a log home about a quarter-mile away. In 1783, Frederick would be called upon to escort on horseback the preacher Elkins to officiate the wedding of Captain Isaac Shelby to Capt. Hart’s daughter Susannah. [2] Shelby, who had surveyed land for the Transylvania Company, went on to serve as the first governor of Kentucky in 1792. It is likely that young Frederick Hart was trained by Jack Hart, one of the highly skilled enslaved men in Capt. Hart’s workforce, who had also served as a pilot guide on Boone’s earlier explorations. In 1803, Jack Hart paid $400 for his manumission to Nathaniel Hart. Jr. and later purchased land near Shelby’s estate, Traveller’s Rest, in Lincoln County, where it is said he is buried in an unmarked grave in the family cemetery.
Next time-- Tracing the Harts: From Frontier to Urban Servitude
Thumbnail: Image of a plaque depicting the Treaty of Watauga at Sycamore Shoals. Courtesy of the University of Kentucky Special Collections Research Center.
About the Author:
Rachel Grimes is a composer and pianist based in Kentucky who creates music for chamber ensembles, orchestras, film, multi-media installations, and collaborative live performances. She is a multi-generational Kentuckian interested in how genealogy and history research can lead to social change. She has been a member of African-American Genealogy Group of Kentucky since 2019, and a Board member since 2024. She is a past Board member of the Port William Historical Society, and is a member of the Filson Historical Society, Madison County Historical Society, and the Fort Boonesborough Foundation. www.rachelgrimespiano.com
Sources and Further Reading:
A History of the Daniel Boone National Forest 1770 - 1970 by Robert F. Collins
African Americans at Fort Boonesborough 1775-1784 by Harry G. Enoch and Anne Crabb
Frankfort Census of Free Blacks 1842 - National Genealogical Society Quarterly Vol. 63, No. 4, Dec. 1975
1850 US Federal Census - Frederick Hart
[1] Orlando Brown, Frankfort Commonwealth, June 1, 1841
[2] Orlando Brown, “The Governors of Kentucky,” Frankfort Commonwealth, January 10, 1861