Henry Skaggs (January 8, 1724 – December 4, 1810. Occasional alternative spellings: "Skeggs" and "Scaggs") was an American longhunter, explorer and pioneer, active primarily on the frontiers of Tennessee and Kentucky during the latter half of the 18th century. His career as an explorer began as early as 1761 as one of the so-called long hunters— men who undertook lengthy hunting expeditions into the Trans-Allegheny wilderness. In subsequent years, working as a land agent with Richard Henderson and Daniel Boone, he explored large parts of Middle Tennessee and Central Kentucky. Skaggs was credited with the rescue of noted kidnap victim, Jenny Wiley in 1790, and with a frontier, vigilante posse, led a pursuit and failed attempt to apprehend America's first known serial killers, the Harpe Brothers in 1799.
Henry Skaggs was born in January 8, 1724, in the Province of Maryland, British Royal Colony, British North America, British Empire to James Skaggs, a Scots-Irish immigrant, and Rachel Susannah Moredock, a native of Fincastle County, Virginia. James Skaggs and his sons, were noted hunters and fur traders.
In 1761, Henry Skaggs joined an expedition, led by Elisha Walden, into Carter's Valley in present-day Hawkins County, Tennessee. This was followed by a 1763 trip deeper into Cumberland territory.
In 1764, Henry Skaggs led his first expedition through the Cumberland Gap, a mountain pass at the junction of Kentucky, Tennessee and Virginia. These early trips westward attracted the interest of famed explorer Daniel Boone. Boone used his existing relationship with North Carolina land speculator Richard Henderson to recruit Skaggs as an agent for Henderson's land company, Richard Henderson and Company. In 1765, Skaggs explored the lower Cumberland River region (upper Middle Tennessee) as an agent of Henderson and established his station near the present day Goodlettsville, Tennessee.
In the Fall of 1769, Henry Skaggs returned to the Cumberland with Kasper Mansker, Joseph Drake and Colonel James Knox. This expedition reached the Dix River in Kentucky, and pressed on to the Green River country. One day on this expedition, the group heard an eerie sound unlike anything they had ever heard before. Mansker pressed forward to investigate only to find the source of the mysterious noise to be Daniel Boone, sprawled on a deerskin singing. The Boones, Daniel and Squire, stayed with the expedition for a week or two, harvesting wild meat and rendering tallow.
Part of the Wilderness Road, crossing Rockcastle County, Kentucky from Hazel Patch to Crab Orchard, was known as "Skaggs Trace," named after Henry Skaggs.
In June 1775, Skaggs, along with Valentine Harman, a member of the Transylvania Convention at Boonesborough in May, led Colonel Thomas Slaughter to the Green River country of Kentucky to explore that land on behalf of Richard Henderson's Transylvania Company, which had recently purchased the area along with a large portion of Central Kentucky.
Skaggs permanently settled in Kentucky in 1789 on Pitman's Creek in Barren County. He is credited with the rescue of the kidnapped pioneer Jenny Wiley from a Native American raiding party at Harman's Station, Kentucky in 1790 by piloting a crude raft made from logs and vines to transport her across the river to the safety of the blockhouse.
In 1799, Skaggs led the frontier pursuit of the notorious serial killers, the Harpe Brothers, in Western Kentucky. Several vigilante posses were formed to look for the escaped criminals, but the only one that found them became frightened and ran. Skaggs, enraged, tried to reform the scattered party and pursue the Harpes, but to no avail. Undeterred, he pressed on alone, and an hour later encountered a crowd of some 20-30 settlers, jigging and drinking in the cabin of some newcomers at the close of a house-raising celebration. Skaggs told them his dire news. The men, already quite drunk, grabbed bottles and rifles indiscriminately and joined the hunt for the Harpes. Once in the forest, however, the posse's enthusiasm evaporated. Once again, Skaggs saw his followers disappear, and continued on alone.
Skaggs came to the cabin of a pioneer named Colonel Daniel Trabue, an old Indian fighter. Trabue agreed to join the hunt for the Harpes as soon as his son returned from an errand to borrow some flour and beans from a neighbor. Unfortunately for Trabue, the famished Harpes found his son first. The son's blood-soaked dog returned to the cabin and led Trabue and Skaggs to the sinkhole where the Harpes had discarded the body. He had been brutally beaten and tomahawked, and his load of supplies was stolen. Skaggs and Trabue searched for days, but never found the Harpes.