John Doleson was a land speculator and early settler of Middle Tennessee, led over one hundred settlers on a tortuous water journey to the Cumberland settlement during the winter of 1779-80. Donelson was one of the earliest settlers of Pittsylvania County, Virginia. Richard Henderson selected Donelson and a man named James Robertson to lead settlers into this Cumberland River region. Robertson made plans for an overland voyage while Donelson led another group along a water route. Donelson and approximately thirty families embarked from Fort Patrick Henry on December 22, 1779. Their boat, the Adventure, accommodated several families, household goods, and supplies necessary to sustain a settlement in a new land. At the mouth of the Clinch River, another group of emigrants joined Donelson's party. He led this flotilla of thirty or so canoes, flat boats, and dugouts on an expedition traversing the Holston, Tennessee, Ohio, and Cumberland Rivers.