A Road Trip on the Wilderness Road in Southwest Virginia

The pages of your history books will absolutely explode to life when you follow the Wilderness Road in Southwest Virginia. Also known as U.S. Route 58, this famed 100-mile stretch of highway follows the path once traveled by westward-bound settlers in the 1700's.

Back then, frontiersman Daniel Boone led the way, blazing the path into Kentucky by way of the Cumberland Gap. This rugged path would later be named the Wilderness Road and would come to be traveled by more than 200,000 early pioneers. All were eager to reach the west in search of better lives, despite severe hardships like bitter cold, hunger, and sickness.

Today, the Daniel Boone Wilderness Trail stretches westward from Bristol to the gateway through the Appalachian Mountains we know as the Cumberland Gap. Along the way, up your knowledge about the westward migration, traverse living history museums and state parks, even explore massive caves and historic settlements.

BRISTOL

Your journey along the Daniel Boone Wilderness Trail may begin in Bristol, but this town is more about the beginnings of country music than westward expansion. Still, it's practically required to stop in the Birthplace of Country Music Museum, if only to get schooled on music recording sessions that ushered in the country music industry.

From here, make your way to State Street, a popular two-mile roadway across town that straddles Virginia and Tennessee, from Lee Highway on the west side of town to Slater Park on the east side of town. On one side of State Street, you're in Virginia. Cross the street, you're in Tennessee. As you can imagine, State Street is wildly popular, especially among those eager to snap an "I was here" photo.

Extend your trip with our complete guide to visiting Bristol. 

GATE CITY

Continue on to stop for lunch at Hob-Nob Drive In on Daniel Boone Road. Fill up on slaw dogs, onion rings, burgers, and tater tots at this family-owned 50s-style diner that's been wooing and wowing customers for more than 60 years. A hand-scooped milkshake is mandatory — they're among the best in the state.

DUFFIELD

From here, Natural Tunnel State Park in nearby Duffield is an easy-breezy 15-minute drive. This stop on Wilderness Road is a two-fer since it captivates both with U.S. history and natural history thanks to its namesake, a massive 10-story limestone cave. This naturally-carved cave is so large that is used as a railroad tunnel through Purchase Ridge.

Even more interesting, this limestone cave is really, really old. As in, more than one million years old. It began to form more than one 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 erosion.

Since 1894, Natural Tunnel has been used as a train tunnel, carrying passengers and natural materials, like iron ore. Today, the tracks that run through Natural Tunnel are operated by Norfolk Southern and are only used to carry coal.

Ride the chairlift down to the base of the tunnel where you can walk along a paved path to the mouth of Natural Tunnel. You can also explore Carter Log Cabin, which sits alongside Stock Creek. Once you return to the top, stroll the Lover's Leap Trail to Lover's Leap Overlook for spectacular views of the tunnel and surrounding area.

In the southeast corner of the park you'll find the Wilderness Road Blockhouse, which was erected in 2003. While not original, it's typical of blockhouses manned in the late-1700s by the Holston Militia, a group of settlers tasked with fending off Native Americans organized by the British.

Continue on to Kane Gap, a natural notch (much like Cumberland Gap) that was a beholden sight for weary settlers slowly moving westward on their way to and through Cumberland Gap. For sensational views of Kane Gap, head west on U.S. Route 58 to Powell Mountain Overlook, which sits between Duffield and Stickleyville.

Alternatively, plan a several-mile scenic hike into Kane Gap along the Daniel Boone Trail. This section of the Virginia Bird & Wildlife Trail ascends a hardwood forest on Powell Mountain and terminates at Kane Gap.

EWING

From here, it's less than a one-hour drive to Wilderness Road State Park. But first, consider a hike to 250-foot-wide half-domed Sand Cave. Tucked away amongst colossal hemlock pines and rhododendron thickets, Sand Cave was once a gigantic sandstone rock. Over millions of years, the wind tirelessly eroded the sandstone, resulting in an oasis-like tract of sand inside a rock cave.

Note: While the sand cave itself isn't technically in Virginia, the trail to reach it begins within the state, so we still recommend journeying to see this awesome natural wonder!

From this same trail that originates from within Civic Park, visitors can scramble to the top of White Rocks. These wide sandstone cliffs were once used as a beacon for westward-bound settlers in search of Cumberland Gap.

Further along U.S. Route 58 you may be greeted by a small herd of buffalo as you drive into Wilderness Road State Park. These mighty creatures are fenced into a pasture steps from the entrance to the 310-acre state park. Before early settlers wearily trudged westward, the indomitable buffalo did the same, forging a buffalo migration path through the gap in Cumberland Mountain.

In the visitor center, brush up on westward expansion, all things Daniel Boone and his role in carving out the Cumberland Gap. You can also rent bikes for a casual ride along yellow-blazed Wilderness Trail or green-blazed Fisherman's Loop. Pack a lunch to enjoy at the wooden picnic table that sits alongside the buffalo pasture along the Wilderness Trail.

Outside, the park features the re-creation of Martin's Station, an outdoor living history museum representing life on Virginia's frontier in 1775. Martin's Station is named for Joseph Martin, a pioneer who arrived in 1769 after an arduous journey to claim 21,000 acres as the first settler on land granted by the Loyal Land Company.

CUMBERLAND GAP

Cumberland Gap National Historical Park is your final stop on this westward expedition along famed Wilderness Road. But first, plan for a short hike along the Tri-State Peak Trail. This forested hike leads to a tripoint with views of Kentucky, Virginia and Tennessee. 

About mid-way 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 painstaking work to forge a historic west-opening path. Post-hike, drive to the park’s visitor center for historic exhibits and artifacts.

A four-mile drive along Skyland Road at Cumberland Gap National Historical Park leads to Pinnacle Overlook. Here you'll be astounded by beyond breathtaking views of Kentucky, Virginia and Tennessee. Close your eyes and imagine the masses of immigrants traveling west in search of available land and improved lives.

There's more to Cumberland Gap than a westward migration path and it lies beneath the earth's surface at Gap Cave. In the visitor center, sign up for a two-hour ranger-led exploration of this majestic underground cavern brimming with dazzling stalagmites and stalactites. Keep your eyes open for small bats fluttering across the four levels of this cave. 

Before Daniel Boone, the first route across Cumberland Gap was by way of the Native American-created "Warrior’s Path." This route was used by Daniel Boone as part of his explorations beyond the mountains prior to 1770.

It wasn't until 1775 that Boone was tapped by Richard Henderson, a wealthy claimant to holdings in the west, to quickly open a westward path over the Cumberland Gap. This largely bushwhacked path was replaced in 1794 by a more settler-friendly wagon road through Cumberland Gap. This wagon road was the principal route used by settlers for more than fifty years to reach Kentucky from the East, serving as the precursor to what is now U.S. Route 58.