Surprisingly  enough, it is not at Liberty, the oldest town. It comes from Watertown, goes straight across the square at Alexandria, passes new Hope Church, goes through Walker’s Creek and on to Smith  Fork near Temperance Hall, and goes down the west side of Smith Fork to Lancaster in Smith County.
This road was blazed out in 1788 and was intended to be the main road from Nashville to Knoxville. If you are a Caney Fork Electric Cooperative customer, you receive the Tennessee magazine, whose November 2011 issue had a picture of two men on the cover.
They are Jack Masters and Bill Puryear, who have done vast  amount of research on the early land grants and roads of Middle Tennessee before 1800. They have compiled a book, ”Thoroughfare for Freedom,” which contains much of this research; the book is available at Justin Potter Library in Smithville.
These men found the First Holston Road, which does not appear on most of the early maps, and traced it from the beginning to the end. The oldest  road in DeKalb County is part of this First Holston Road, which was marked out in 1788, about 10 years before our first settlers moved into what is now DeKalb County.
The First Holston Road on the south side of Cumberland River was blazed out in May 1788. It was advertised like this; “By this new road a pleasant passage may be had to the western county with carriages, with an easy ascent of Cumberland Mountains, and beyond it, the road is generally level and firm, abounding with fine springs of water.” This was, however, false advertising, and Col. William Martin said it was never much more than a packhorse road. By 1797 James Winchester remarked that it was”much disused.”
However, the First Holston Road was evidently the very road used by the first settlers of DeKalb County when they came from Nashville in 1798. It began near Clover Bottom just east  of Nashville, and passed very near to what is now Lebanon. From there it followed very closely the present Highway 70, through Watertown and on to what is now Alexandria. The road continued past New Hope Church through Walker’s Creek, and to Smith Fork near Temperance Hall. Passing through Lancaster, it crossed the Caney Fork on the western end of the Moss Bend and passed through Possum Valley and Rock Springs Branch to join the Main Holston Road (by 1802 called the Walton Road) on to Knoxville.
The First Holston Road was not much of a road; it was narrow and had no bridges and was certainly not suitable for wagons to travel. However, it was a track to follow, and many miles of our present highway to Nashville follows the same track more than 200 years later. The Alexandria location seems to be where the parting of the ways came. Adam Dale and the Fite brothers, John and Leonard, planned to settle on Smith Fork at what would eventually become Liberty.  No road existed from Alexandria location, and the  families had to cut their own road to the Liberty location as described in Chapter III (page 27) of “A Bicentennial History of Dekalb County” by Thomas G.Webb.
Stephen Robinson is thought to have come in 1798 with th Fite brothers and Adam Dale, but he apparently  continued east on the First Holston Road to the Temperance Hall area. He was definitely  there in 1798, not far from John Lancaster, who was building a mill in what is now Smith County. Daniel Alexander stopped at the Alexandria location, and was living there in June 1801 in a large two-story log house; in 1802 he was granted license to operate a tavern there. A few years later he laid off town lots and named the place Alexandria for himself. DeKalb County’s oldest road is very much in use today. All of it is paved, part of it is  now in Highway 70, and the remainder is used every day as a part of DeKalb County’s road system. And we know now that our first settlers at Liberty in 1798 did not have to cut their own roads from Nashville all the way to Liberty. They had at least a track to follow as far as the Alexandria location before they had to begin cutting their own way through the wilderness.