29 July, 2021
A road trip on the Wilderness Road in southwest Virginia

A road trip on the Wilderness Road in southwest Virginia

The pages of your history books come to life when you set your GPS for Wilderness Road in southwest Virginia. This famous 100-mile stretch of the highway, also known as US Route 58, follows the path that settlers once traveled westward in the 1700s.

Back then, frontier worker Daniel Boone led the way and courageously paved the way to Kentucky over the Cumberland Gap. This rugged trail was later known as the Wilderness Road and was used by more than 200,000 early pioneers. Everyone was eager to reach the West in search of a better life, despite severe difficulties such as bitter cold, hunger and disease, even attacks by Native Americans.

Photo credit: Scott County Tourism

Today the Daniel Boone Wilderness Trail stretches west from Bristol to the gateway through the Appalachian Mountains we know as the Cumberland Gap. Along the way, you can expand your knowledge of migration west, traverse living historical museums and state parks, and even explore vast caves and historic settlements.


Your journey along the Daniel Boone Wilderness Trail may begin in Bristol, but this city is more about the beginnings of country music than its expansion westward. Still, it is practically necessary to stop at the Country Music Museum’s birthplace if all you want to do is learn music recordings that ushered in the country music industry.


From here, make your way to State Street, a popular two-mile-long straight across town that stretches across Virginia and Tennessee, from the Lee Highway on the west side of town to Slater Park on the east side of town. You are on one side of State Street in Virginia. Cross the street, you’re in Tennessee. As you can imagine, State Street is very popular, especially with those who want to take a photo titled “I Was Here” for the gram.


Make Homeplace Mountain Farm in Gate City your next stop along Wilderness Road. This open-air living history museum is a short 35-minute drive from Bristol. It’s an ideal stretcher stop if you’re walking a converted farm. Imagine what life was like as you approach the original structures of the early pioneers in Southwest Virginia.

Photo credit: Scott County Tourism

Continue for lunch at Hob-Nob Drive-In on Daniel Boone Road. Indulge yourself with coleslaw dogs, onion rings, burgers and tater tots at this family-run 1950s-style restaurant that has been courting and delighting customers for more than 60 years. PS, a hand-scooped milkshake is mandatory. The milkshakes are some of the best in the state.


From here, the Natural Tunnel State Park in nearby Duffield is a 15-minute drive away. This stop on Wilderness Road is a stopover as it has a fascination for both US history and natural history thanks to its namesake, a massive 10-story limestone cave. This naturally carved cave is so large that it doubles as a railroad tunnel through Purchase Ridge.


Photo credit: Scott K. Brown

What’s even more interesting is that this limestone cave is really, really old. As in, more than a million years old. Well, it began to form more than a million years ago when acid-infused groundwater began to seep through crevices, slowly dissolving the limestone and bedrock. An underground river called Stock Creek also contributed to the erosion.

The natural tunnel has been used as a railway tunnel since 1894, transporting passengers and natural materials such as iron ore. Today the tracks that run through the natural tunnel are operated by Norfolk Southern and are only used to transport coal.

Take the chairlift to the base of the tunnel, where you can walk on a paved path to the mouth of the natural tunnel. You can also explore Carter Log Cabin, which is located next to Stock Creek. When you get back to the top, walk the Lover’s Leap Trail to the Lover’s Leap Overlook for spectacular views of the tunnel and the surrounding area.


Photo credit: Scott K. Brown

In the southeast corner of the park is the Wilderness Road Historical Area. Here you can explore the Wilderness Road Blockhouse, which was built in 2003. While not original, it is typical of log houses that were occupied by the Holston Militia in the late 18th century, a group of settlers whose job it is to fend off British-organized Indians.


Photo Credit: Joshua Moore, IG Account: @ jtm71

Continue to Kane Gap, a natural notch (similar to Cumberland Gap) that was a must-see for weary settlers moving slowly west on their way to and through Cumberland Gap. For sensational views of Kane Gap, head west on US Route 58 to Powell Mountain Overlook, located between Duffield and Stickleyville.

Alternatively, plan a mile-long hike along the Daniel Boone Trail to Kane Gap. This section of the Virginia Bird and Wildlife Trail runs through a hardwood forest on Powell Mountain and ends in Kane Gap.


From here it is less than an hour’s drive to Wilderness Road State Park. But first, consider a hike to the 250 foot wide, semi-arched sand cave. The Sand Cave was once a gigantic sandstone rock, hidden between colossal hemlock pines and rhododendron thickets. Over millions of years, the wind tirelessly eroded the sandstone, resulting in an oasis-like piece of sand in a rock cave.

Photo credit: Erin Gifford

The same trail that came from Civic Park allows visitors to climb to the top of White Rocks. These broad sandstone cliffs were once used as beacons for settlers heading west in search of Cumberland Gap.

Photo credit: Erin Gifford

Continuing along US Route 58, a small herd of buffalo greets you as you drive into Wilderness Road State Park. These powerful creatures are fenced in in a pasture from the entrance to the 310 acre state park. Before early settlers tiredly trudged west, the indomitable buffalo did the same, making a buffalo trail through the Gap in Cumberland Mountain.

At the visitor center, freshen up westward expansion, all that Daniel Boone and his role in carving out the Cumberland Gap has to offer. You can also rent bikes from the visitor center for a casual ride along the glowing yellow Wilderness Trail or the glowing green Fisherman’s Loop. Pack lunch to enjoy at the wooden picnic table next to the buffalo pasture along the Wilderness Trail.

In the visitor center, the award-winning docudrama “Wilderness Road, Spirit of a Nation” tells the story of the pioneers’ Western movement. There is also a gift shop and a small border museum in the visitor center.

Out in the park is the redesign of Martin’s Station, an outdoor living history museum that depicts life on the Virginia border in 1775. Martin’s Station is named after Joseph Martin, a pioneer who arrived in 1769 after a strenuous journey to claim 21,000 acres as the first settler on land granted by the Loyal Land Company.


The Cumberland Gap National Historical Park is your final stop on this expedition west along the famous Wilderness Road. First, plan a short hike along the Tri-State Peak Trail. This wooded hike leads to a tripoint overlooking Kentucky, Virginia, and Tennessee. Stop along the way to read posters like “A Hard Road To A New Life” and get a glimpse of the challenges early settlers faced on their way west.


Photo credit: Keith Lanpher

About halfway through the hike, you’ll see a pyramid-shaped marker celebrating Daniel Boone’s Trail. This was placed by the Tennessee Daughters of the American Revolution to commemorate his meticulous work to find a historic path west. After the hike, head to the park’s visitor center to see historical exhibits and artifacts.


Photo Credit: Joshua Moore, IG Account: @ jtm71

A four mile drive along Skyland Road in the Cumberland Gap National Historical Park leads to the Pinnacle Overlook. Here you will be amazed by the breathtaking views of Kentucky, Virginia and Tennessee. Close your eyes and imagine the masses of immigrants traveling west in search of available land and an improved life.

Cumberland Gap offers more than one hiking trail to the west and is underground in Gap Cave. Sign up at the visitor center for a two-hour exploration of this majestic underground cave filled with dazzling stalagmites and stalactites. Keep your eyes peeled for tiny bats fluttering across the four levels of this cave.


Photo credit: Tim Cox

Before Daniel Boone, before the mighty buffalo, the first route led over Cumberland Gap on the “Warrior’s Path” created by the Native Americans. This route was used by Daniel Boone as part of his explorations beyond the mountains before 1770.

It was not until 1775 that Boone was opened up by Richard Henderson, a wealthy applicant for stakes in the west, to quickly open a route west across the Cumberland Gap. This largely bush-lashed path was replaced by a more settler-friendly wagon road through Cumberland Gap in 1794. This wagon road was the main route used by settlers to reach Kentucky from the east for more than fifty years. It served as the forerunner of today’s US Route 58.

A Road Trip on Wilderness Road in southwest Virginia first appeared on Virginia’s travel blog.

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