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The Skagg's Trace was a hunters' trail leading from Flat Lick to the Dick's (now Dix River in Lincoln County. It was named for Henry or Richard Skaggs, who hunted in Kentucky as early as 1769. Skagg's Trace left the Warriors' Path at Flat Lick in Knox County, Crossed Stinking Creek, and headed northwest along the west branch of Turkey Creek, almost as U.S. 25E does today. It passed north of present-day Barbourville, westward along Poplar Branch of Richland Creek, then northward across several western branches of the Middle Fork. It crossed Robinson Creek, passed Raccoon Spring, and reached Laurel River at happy Hollow Branch. The old trace went through what is now the Levi Jackson SMe Park and followed the Little Laurel River northward, passing what is now London to the east. From the headwaters of the Little Laurel River, it went to the headwaters of Hazel Patch Creek, down the creek to the Rockcastic River, down that river to Skeggs Creek, and up Skeggs Creek to the headwaters. From there it crossed over the Little Negro Creek, a branch of Dick's River and went down Dick's River to Crab Orchard and Stanford. This road was extended through Harrodsburg to Louisville by 1779.

It is believed that more pioneer families used Skagg's Trace than Boone's Trace when journeying to Kentucky. See Robert L. Kincaid, The Wilderness Road (Middlesborougk KY., 1966); Neat Hammon, "Early Roads into Kentucky," Register 68 (April 1970):118-23. Neat 0. Hammon