Often traveling single file through the deep woods and thick cane bottoms of the region, herds of buffalo, properly named American Bison, were the first road builders in this area.  In search of salt, necessary for their survival, the animals would move from licks or areas of natural salt deposits that were sometimes found near creeks.  The animals were not inclined to maneuver in the creek beds, avoiding the slippery, dangerous rocks, instead preferring to drink from the creek banks and to travel through the adjacent bottomlands.  One such salt lick, Buffalo Springs, noted in early deeds as “the Buffaloe Spring”, was located south of present day Westmoreland on Bledsoe Creek.

These same trails were often used as natural avenues by Native Americans, both for hunting purposes and as wartraces leading to the frontier settlements near the Cumberland River.  And the first Europeans cautiously navigated these same routes, first as parties of long hunters and later as paths to their first permanent settlements.  

A well-worn series of buffalo traces followed the bottomlands of both Little Trammel and Garrett’s Creek from Cantuckee south to their beginnings then down the ridge in both the Rock House and Gregory Hollows, merging near the Buffalo Springs and then continuing southward through the bottomlands of Bledsoe’s Creek to Castalian Springs and the Cumberland River beyond.  Indians frequently traversed this trail and the first Europeans that passed through what would later become Westmoreland followed this same path.  

In the fall of 1771, Kasper Mansker, Issac Bledsoe, and Joseph Drake led a party of long hunters along this trail, establishing their Station Camp along the creek between Gallatin and Hendersonville that still bears that name and hunting and exploring along Manskers, Bledsoe, and Drakes Creeks.  Frequently harassed by Indian raiding parties intent on protecting their historic hunting lands, the long hunters departed the area in the late fall of 1772, passing again through today’s Westmoreland along the buffalo trace.  Three years later, in November, 1775, Kasper Mansker would again lead a smaller group of long hunters along this same trail to encamp at Mansker’s Lick.  

Hearing stories told by Mansker, Bledsoe, and others, Thomas Sharpe Spencer came to the area via Westmoreland’s buffalo trace in 1776.  A giant of a man and appropriately nicknamed “Bigfoot”, Spencer was accompanied by several others, namely John Holliday.  Eventually, however, the others returned east, leaving Spencer alone in the wilderness, where he remained until 1778.  He is often referred to as Sumner County’s first permanent settler of European heritage.  

North of Bethpage, the route of today’s Old Highway 31-E follows the old buffalo trail up the ridge and through Westmoreland where the trail veered to the northeast, roughly following Pleasant Grove Road to its intersection with New Highway 31-E, and then north to Kentucky along the bottomlands of Garrett’s Creek.  South of Bethpage, the trail originally followed the path that, in 1886, would become the route of the Chesapeake and Nashville Railway.  Early settlers referred to this road as the Kentucky Road.  Its extension into Kentucky was officially named by that state in 1800 the “Upper Louisville – Nashville Road”.  Kentucky did a better job of maintaining the road than did Tennessee with Tennessee’s portion being not much more than a rough path until 1837, though Sumner County first began making efforts to improve it in 1802.  (It should be noted that in its second meeting, the Sumner County Court, then officially named the Court of Pleas and Quarter Sessions of Sumner County, North Carolina, ordered the clearing of two roads, “sufficient for pack horses to pass”.  The first road was to run from Major Isaac Bledsoe’s to the state line following “the most convenient way to the Blue Spring.”  This first-sanctioned road in Sumner County was the forerunner of Highway 31-E.  The motion for the creation of the road was passed in July, 1787, and Anthony Bledsoe was chairman of the court.) 

Beginning in February, 1837, the Gallatin Turnpike Company, with state help, began construction on an improved thoroughfare, ultimately running from the state line to Nashville.  The 49.5 mile road was 60 feet wide with twelve stone bridges, one additional wooden bridge, 30.5 miles of macadamized or compacted stone and 15 miles of graveled road.  This road followed the route of the “old road to Gallatin” familiar to older residents and continuing north of what would much later become the communities of Westmoreland, Turner’s Station, Sugar Grove, and beyond to Kentucky.  This was the first of two roads substantially important to the settlement of the ridge area of northeastern Sumner County.