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The itineraries of early travelers describe the Wilderness Road in definite terms. One of the earliest is that given by John Filson, whose history of Kentucky was published as early as 1784. It described the route from Philadelphia to Louisville (eight hundred and twenty-six miles), as follows:

Miles
From Philadelphia to Lancaster,66
To Wright’s on the Susquehanna,10
To Yorktown,12
To Abbotstown,15
To Hunterstown,10
To mountain at Black’s Gap,3
To other side of the mountain,7
To Stone-house Tavern,25
To Wadkin’s Ferry on Potomac14
To Martinsburg,13
To Winchester,13
To Newtown,8
To Stoverstown,10
To Woodstock,12
To Shenandoah River,15
To North Branch Shenandoah,29
To Staunton,15
To North Fork James River,37
To Botetourt C. H.,12
To Woods on Catawba River21
To Paterson.s. on Roanoke,9
To Alleghany Mountain,8
To New River,12
To Forks of Road,16
To Fort Chissel,12
To Stone Mill,11
To Boyds,8
To Head of Holstein,5
To Washington C. H.,45
To the Block-house,35
To Powell Mountain,33
To Walden’s Ridge,3
To Valley Station,4
To Martin’s Cabin,25
To Cumberland Mountain,20
To Cumberland River,13
To Flat Lick,9
To Stinking Creek,2
To Richland Creek,7
Down Richland Creek,8
To Racoon Spring,6
To Laurel River,2
To Hazel Patch,15
To Rockcastle River,10
To English Station,25
To Col. Edward’s Crab Orchard,3
To Whitley’s Station,5
To Logan’s Station,5
To Clark’s Station,7
To Crow’s Station,4
To Harrod’s Station,3
To Harlands’,4
To Harbisons,10
To Bardstown,25
To Salt Works,25
To Falls of the Ohio,20
——
826

Mr. Speed preserves for us the itinerary with “observations and occurrences” of William Brown, the father of Judge Alfred M. Brown, of Elizabeth town, Kentucky. “It is contained in a small manuscript book,” writes Mr. Speed, “which has been preserved in the family. It is especially interesting from the fact that immediately upon his arrival in Kentucky, by the journey of which he made a complete record, the Battle of Blue Licks occurred. He aided in burying the slain, among whom was his own brother, James Brown.” The itinerary and “observations and occurrences” follow:[9]

(1782)

“Hanover to Richmond, Henrico Co.,18
To Widow Simpson’s, Chesterford,14
To Powhatan Co. House,16
To Joseph Thompson’s at the forks of the road,8
To Long’s Ordinary, Buckingham,9
To Hoolen’s on Willis Creek,8
To Mrs. Sanders, Cumberland,3
To Widow Thompson’s passing Hood’s and Swiney’s,27
To Captain Hunter’s,5
To Thompson’s on the Long Mo., Campbell,5
To Dupriest,6
To New London,10
To Liberty Town,16
To Yearley’s, at Goose Creek, Bedford,12
To M. Loland, at the Blue Ridge Gap,6
To Big Flat Lick,10
To Fort Lewis, Botetourt,12
To Hans’ Meadows,20
To English’s Ferry, New River,12
To Fort Chiswell,30
To Atkins’ Ordinary,19
To Mid Fork Holstein,—
To Cross White’s, Montgomery,3
To Col. Arthur Campbell’s,3
To 7-mile Ford of Holstein,6
To Maj. Dysart’s Mill,12
To Washington Co. House,10
To Head of Reedy Creek, Sullivan Co., North Carolina, 20
To Block House,13
To North Fork Holstein,2
To Moccasin Gap,5
To Clinch River,11
To Ford of Stock Creek,2
To Little Flat Lick,5
To North Fork of Clinch,1
To Powell’s Mountain,1
To Wallan Ridge,5
To Valley Station,5
To Powell’s River,2
To Glade Spring,4
To Martin’s Station,19
To Big Spring,12
To Cumberland Mountain Gap,8
To Yellow Creek,2
To Cumberland River,13
To Big Flat Lick,9
To Little Richland Creek,10
To Big Richland Creek,1
To Robinson Creek,10
To Raccoon Spring,1
To Laurel River,2
To Little Laurel River,5
To Raccoon Creek,8
To Hazel Patch,4
To Rockcastle Creek,6
To Rockcastle River,7
To Scaggs’ Creek,5
To Head of Dicks River,15
To English Station,8
To Crab Orchard,3
To Logan’s Old Fort,11
To Doehurty’s Station,8
To Harrod’s Station,6
To Harrodsburg,6
From Hanover to Harrodsburg is 555 miles.

Observations and Occurrences: Set Out from Hanover Monday, 27th May, 1782; arrived at the Block-house about the first week in July. The road from Hanover to this place is generally very good; crossing the Blue Ridge is not bad; there is not more than a small hill with some winding to go over. Neither is the Alleghany Mountain by any means difficult at this gap. There are one or two high hills about New River and Fort Chiswell. The ford of New River is rather bad; therefore we thought it advisable to cross in the ferry-boat. This is generally a good-watered road as far as the Block-house. We waited hereabouts near two weeks for company, and then set out for the wilderness with twelve men and ten guns, this being Thursday, 18th July. The road from this until you get over Wallen’s Ridge generally is bad, some part very much so, particularly about Stock Creek and Stock Creek Ridge. It is a very mountainous country hereabout, but there is some fine land in the bottoms, near the watercourses, in narrow slips. It will be but a thin settled country whenever it is settled. The fords of Holstein and Clinch are both good in dry weather, but in a rainy season you are often obliged to raft over. From them along down Powell’s Valley until you get to Cumberland Gap is pretty good; this valley is formed by Cumberland Mountain on the northwest, and Powell Mountain on the southeast, and appears to bear from northeast southwestwardly, and is, I suppose, about one hundred miles in length, and from ten to twelve miles in breadth. The land generally is good, and is an exceeding well-watered country, as well as the country on Holstein River, abounding with fine springs and little brooks. For about fifty miles, as you travel along the valley, Cumberland Mountain appears to be a very high ridge of white rocks, inaccessible in most places to either man or beast, and affords a wild, romantic prospect. The way through the gap is not very difficult, but from its situation travelers may be attacked in some places, crossing the mountain, by the enemy to a very great disadvantage. From thence until you pass Rockcastle River there is very little good road; this tract of country is very mountainous, and badly watered along the trace, especially for springs. There is some good land on the water-courses, and just on this side Cumberland River appears to be a good tract, and within a few years I expect to have a settlement on it. Some parts of the road are very miry in rainy weather. The fords of Cumberland and Rockcastle are both good unless the waters be too high; after you cross Rockcastle there are a few high hills, and the rest of the way tolerable good; the land appears to be rather weak, chiefly timbered with oak, etc. The first of the Kentucky waters you touch upon is the head of Dick’s River, just eight miles from English’s. Here we arrived Thursday, 25th inst., which is just seven days since we started from the Block-house. Monday, 29th inst., I got to Harrodsburg, and saw brother James. The next day we parted, as he was about setting off on a journey to Cumberland.

On Monday, August 19th, Colonel John Todd, with a party of one hundred and eighty-two of our men, attacked a body of Indians, supposed to number six or seven hundred, at the Blue Lick, and was defeated, with the loss of sixty-five persons missing and slain.