Virginia Sellards Wiley was born about 1760 in Pennsylvania. When Jennie was a small child, however, the family moved to the settlement at Walker's Creek in present-day Bland County, Virginia. Jenny married Thomas Wiley in 1779. Native American attacks on Walker's Creek were a consistent problem, and Mrs. Wiley had defended her family of four children on occasion.
One night in 1789, Thomas Wiley was away from the home, which was occupied by Jenny, her brother, and the four Wiley children. Enraged by the death of a Cherokee chief's son, who had been killed by famed fighter Matthias Harman and his group of eastern Kentucky settlers, a group of Native Americans arrived at Walker's Creek intent on finding the hunters. Instead, however, they mistakenly entered the Wiley family home, killed three of the Wiley children and their uncle, and took Jenny Wiley and her baby captive.
When it was discovered that Wiley and her baby were missing, a party led by Matthias Harman left Walker's Creek to find them. Their efforts, however, were unsuccessful. For the next several months, Mrs. Wiley remained a Cherokee captive, while her baby, Tommy, succumbed to the harsh conditions early in captivity. His mother, aided by a Shawnee chief traveling with the band, continued marching westward. The group eventually reached the Ohio River, which was flooded. Determining it to be impassable, the group changed course until they reached the banks of the Little Sandy River. There, the Cherokee departed, leaving Wiley as a Shawnee captive.
After Wiley became ill in the winter, the Native Americans set up camp. There, Wiley was given much of the same consideration as any other Shawnee tribe member, including her own rockhouse. Marching continued in the spring, and ended at Mudlick Falls near Paintsville. Again, Wiley worked alongside the Shawnee, hunting, gathering wood, and performing other chores she was assigned.
The return of the Cherokee placed Wiley in great danger when the Cherokee chief purchased her from the Shawnee. While she was a slave of the Cherokee, Wiley had a dream of her escape down several waterways, eventually reaching a fort rescued by Henry Skaggs. It was this path Wiley followed the next day to freedom after eleven months of captivity.
The fort was Harman's Station in Johnson County, a settlement formed by Mathias Harman and fellow Walker's Creek residents. The group had been working on plans to establish the fort during the autumn of her capture. The Wiley family dog, which had been with Jenny throughout her captivity, also survived. Mrs. Wiley returned to her husband at Walker's Creek and the two relocated to Johnson County, where they had five more children. Jenny died in 1831, and was buried in Johnson County.