Shaped by Native American paths and old buffalo traces, the Wilderness Road was forged in 1775 by Daniel Boone for the Transylvania Company. The trail, and later the road, winded through the Cumberland Gap–a notch in the Appalachian Mountains located near the intersection of Kentucky, Virginia and Tennessee–through the interior of Kentucky and to the Ohio River.

The Wilderness Road served as an avenue of westward migration for some 300,000 settlers and led to the establishment of the first settlements in Kentucky and to Kentucky’s admission to the Union in 1792.  By the early 1790’s the trail was being widened to accommodate wagon traffic and was commonly being referred to as Wilderness Road. Private contractors, authorized to keep up sections of the road, charged tolls for its use; however, the building of the National Road and an increase in the use of water ways for travel initiated a decrease in the use of the Wilderness Road and, by the 1840’s, the Road was essentially abandoned.

Since 1926 the Wilderness Road has been linked to U.S. Route 25 (the Dixie Highway) connecting Detroit, Michigan to Miami, Florida.  Like the Wilderness Road before it (which brought settlers and supplies westward), the Dixie Highway brought travelers and tourism to rural areas.