I found a really good resource for those who are researching early settlers of Kentucky. In this article it shares the location of where it was located and the towns that it traveled through.
|The first written record of the Wilderness Road is an announcement in the Kentucky Gazette on October 15, 1796: “The Wilderness Road from Cumberland Gap to the settlements in Kentucky is now completed. Wagon’s loaded with a ton weight, may pass with ease, with four good horses.” Before that time, most people called the route either Kentucky Road or the road to the Holston settlements, depending upon the direction of travel. On John Filson‘s map, the old trail is called “The Road from the Old settle[ments] thro’ the great Wilderness.”
The Wilderness Road more or less followed the old Warriors’ Path through the Cumberland Gap to Flat Lick, then parts of Skaggs’s Trace from Flat Lick to Crab Orchard, Kentucky. Old trails and county roads that extended from Crab Orchard to Harrodsburg and Louisville are also frequently called the Wilderness Road by historians. To follow the Wilderness Road today, the traveler starts from Gate City, Virginia, and takes U.S. 58 to Jonesville. At this point the old road went northward to the base of the Cumberland Mountains and followed the mountains southwest to the Cumberland Gap after rejoining U.S. 58 east of today’s Rose Hill, Virginia. Martin’s Station was located on the road near Rose Hill and Davis Station was on the Kentucky side of the gap, in what is now national park land. From Cumberland Gap to present-day Baughman, Kentucky, the Wilderness Road was nearly the same as U.S. 25E, except that it followed the west side of Yellow Creek north of Middlesboro and the east side of the Cumberland River north of Pineville.
The original route ran north of the present Barbourville, then joined and followed KY 229 to present-day London. Modrel’s Station was built along the road on the west side of the Little Laurel River in 1795; twenty-two militia were stationed there. North of London the road was approximately the same as U.S. 25 to Wood Creek, where it turned north and led to the top of Wildcat Mountain, where there was a trench battle during the Civil War . Farther north, the road ran along the ridge inside the bend in Rockcastle River, ascended on the northwest side, and crossed the river at Ford Creek below Livingston. The road then went up the south fork of Ford Hollow Creek to Sand Hill and followed the former Chestnut Ridge road into present-day Mt. Vernon. Part of the old road was destroyed during the construction of interstate highway I-75.
West of Mt. Vernon the original Wilderness Road is still visible, crossing Little Renfro Creek about 1.5 miles below U.S. 150, and following Boone’s Fork of the Dick’s (now Dix) River to Brodhead. The road followed the north side of the river for about two miles to a salt lick, then crossed to the south side, and followed for the most part U.S. 150 into Crab Orchard. From this point, travelers took county roads to their destinations. One of the most frequently used routes northward from Crab Orchard led to Danville and Harrodsburg, then to the salt works at Bullitt’s Lick, and finally to Louisville. Another road to Louisville from Harrodsburg ran north along the town fork of Salt River past McAfee’s Station to Hammons Creek, then across Big Benson Creek to Squire Boone’s Station, and westward past Lynn’s Station, Asturgus’s Station, the Dutch Station, Floyd’s Station, and the Spring Station.
The original Wilderness Road was not paved, but logs were added later in some sections as a surface material; one such section of corduroy road near Wildcat Mountain could still be seen as late as 1970. The log surfaces were probably installed by the Union army during the Civil War to support artillery and heavily loaded army wagons. On the north side of Wildcat Mountain, two parallel roads led up the hill, about sixty feet apart. One lane was used by double-teamed wagons going up the hill, the other by the spare horses going back down the hill to be double-teamed to another wagon.
Robert L. Kincaid, The Wilderness Road (Middlesborough, Ky., 1966)
Neal Hammon, “Early Roads into Kentucky,” Register 68 (April 1970): 91-131.
In the print edition this entry appears on pages 952 – 953