Walnut Hill was at one time the intersection of two of the main roads in Illinois: the George Rogers Clark Trace, and the Yadda Road.
The original capital of Illinois was at Kaskaskia. The overland route from Kaskaskia to the interior of the State followed the Kaskaskia/Big Muddy divide, which went through Walnut Hill. George Rogers Clark marched through Walnut Hill in February, 1779 in his march from Fort Kaskaskia to Fort Vincennes, which resulted in the conquest of Illinois by the army of Virginia.
Traces of the Kaskaskia/Vincennes road can be seen in several short stretches of road in northwestern Jefferson County, which point toward Walnut Hill, ignoring the surveyed Section boundaries. Northeast of Walnut Hill, the Kell Road is a winding, pioneer road up to its intersection with Interstate 57, from which it follows the modern Section lines to Kell.
Walnut Hill was also on the Goshen Road, an early road across Illinois, from Shawneetown to the Goshen Settlement near Glen Carbon. Remnants of the Goshen Road can be seen in short segments of pioneer road between Dix and Walnut Hill. It is possible that construction of the railroad tracks from Dix to Walnut Hill obliterated much of the original Goshen road.
In 1823, Thomas D. Minor built a road from Mt. Vernon to Walnut Hill. This was called the "Vandalia Road", in that it connected with roads to the new State capital in Vandalia. The new road joined the Goshen Road just south of Walnut Hill. Today it is called the "Old Centralia Road". The new road eventually captured much of the traffic on the Goshen Road, since it provided a shorter route across Jefferson County.
The modern road running northwest out of Walnut Hill toward Centralia is the same as the Goshen Road as shown on the original survey maps of Illinois.
In the early 19th century, William Goins [Goings] kept a tavern that was presumably on land homesteaded by Goings about two miles south of Walnut Hill (in Jefferson County). Goings headed a band of robbers known as the "Goings Gang" that preyed on frontier travelers on the Vincennes-St. Louis Trace, a dirt road or path that extended east-west between these two settlements across southern Illinois. The gang members operated a series of frontier taverns along this road, passing information on to each other whenever a traveler worth robbing stopped at one of their taverns. When the unfortunate traveler reached a remote spot, the gang members would assemble and relieve him of his property. As in other frontier areas, neighboring settlers overlooked this activity until the Goings Gang escalated to murder in 1818-1819. In response, the settlers organized a group of vigilantes or "rangers" who surprised the gang at Walnut Hills. The gang members were tied to trees, flogged, and ordered to leave the county, an order which all but one obeyed. The following year the vigilantes returned and cropped the ears of this obstinate gang member, who may have been William Goings, possibly because they believed he had no use for his ears as he would not listen. The tavern site of one of the reported gang members—Samuel Young of Marion County—was excavated by archaeologists working for the Illinois Department of Transportation in 1988 prior to its destruction by a highway project