The Clarks are truly in the wilderness when they left Mr. Freemans on the morning on 5 November 1809. Cold last night a heavy frost this morning, set out early, breakfast at Mr. (Daniel or William) Anderson- cost 1.50.⁽¹⁾ Stayed all night at Mr. (Joseph) Rileys- cost 3.00 ⁽²⁾ our company left us Roads vey muddy and bad- made 20 miles. Even under difficult weather and road conditions they still made 20 miles. 

6 November, Set out early, cold and heavy frost, breakfast at Mr. (Richard or John) Herndons –cost – 1.50 ⁽³⁾ at Big Stinkin, good house. (Stinking Creek and Old Flat Lick a.k.a. Big Flat Lick are very near each other). The Herndon House could have been at Old Flat Lick.⁽⁴⁾ Stayed all night (at) Mr. (William, Thomas, Richard, & Hendrick) Whites ⁽⁵⁾ 20 miles – cost – 4.50.

Today the heavy wooded area that the Clark party had passed through can be seen at Pine Mountain State Resort Park, Pineville.⁽⁶⁾ Lilly Cornett Woods, (37°05’51” N 82°59’03”.4 W) Letcher Co, KY, is a 554 AC preserve with 252 AC of old growth forest with seasonally-led tours.⁽⁷⁾ The magnificent wildlife that roamed through the Boone Trace-Wilderness Road area of Southeastern Kentucky can be seen at the Boone Ridge Wildlife Center near Pineville, KY (under construction).

For the general route of travel today from the Levi Jackson Wilderness Road Park to Middlesboro, follow KY 229 to US 25E South. The Boone Trace-Wilderness Road was little more than a trail large enough for a horse until 1795 when Kentucky’s First Governor Isaac Shelby and the General Assembly authorized the improvement and relocation of the horse path that became the Wilderness Road. The State had no public fund for road improvement so leading citizens, including Gov. Shelby, “passed the hat” to secure funding for improvements.⁽⁸⁾ Historians, surveyors, geographers including Fox, Hammon, Jones, Kincaid, Meyer, Pusey, Shattuck, and others have researched and written tirelessly to define the Warriors Path, Boone Trace, and Wilderness Road with its many branches and “cutoffs”. In all their writings there are varying degrees of un-certainty in describing the road that had many paths much like the braided streams William Clark had observed in the West. After three days of travel in the mud and rain through the wilderness the Clark party is now facing two mountains.