ROAD SORTIES Scenic Roads

Daniel Boone Heritage Trail

Daniel Boone Heritage Trail is a State Scenic Byway in Virginia. The map below shows its route. Use “Plan a drive” to open it in the Road Sorties route planner — already routing along Daniel Boone Heritage Trail with scenic roads turned on, ready to add your own stops.

The Daniel Boone Heritage Trail is a Virginia Byway on US 23 and US 58 between the Tennessee line below Weber City and Cumberland Gap. It is a separate byway from the Trail of the Lonesome Pine, which the General Assembly designated in the same 1993 act. The Assembly had given that name in 1988 to the highway that runs on US 23 from the Tennessee line south of Weber City, with US 58 joining it at Weber City, to the point south of Duffield where the two part, then on US 58 alone to the state line at Cumberland Gap. The Lonesome Pine byway, by contrast, is a much longer set of roads farther north, among them US 19, US 58 Alternate through Norton and Big Stone Gap, US 23 to Pound and SR 160 out of Appalachia, and this drive follows none of it. The Boone route keeps close to the line of the Wilderness Road, which Daniel Boone and a crew of 35 axmen began cutting in March 1775 from the Long Island of the Holston at Kingsport, Tennessee. It went north through Moccasin Gap in Clinch Mountain, over the Clinch River and the rough country called the Devils Raceway, then southwest down the Powell River valley to Cumberland Gap. Virginia State Parks says more than 300,000 settlers had taken it west into Kentucky and the Midwest by 1800. Out of Weber City, US 23 and US 58 pass through Moccasin Gap beside Moccasin Creek, bypass the centre of Gate City along the foot of Clinch Mountain and follow the Clinch River up to Clinchport. Near Glenita the railroad branches off to run through Natural Tunnel, the heart of Natural Tunnel State Park, about a mile east of the highway. Worn through a limestone ridge, the tunnel is more than 850 feet long and about ten stories tall, coal trains still use it, and the park adds a seasonal chairlift down to the tunnel floor and a Wilderness Road blockhouse exhibit; its Daniel Boone Wilderness Trail Interpretive Center is in Duffield. Just south of Duffield, US 58 leaves US 23 and heads west, signed Daniel Boone Trail as far as Jonesville and Wilderness Road from there to the Gap. Five miles west of Ewing, and ten east of Cumberland Gap National Historical Park, Wilderness Road State Park holds a reconstruction of Martin's Station, the frontier post Joseph Martin first settled in 1769 and came back to in 1775. It is run as an outdoor living-history museum and is open seasonally, and the park also has a visitor center, an 1878 mansion and 6.5 miles of Wilderness Road Trail open to hikers, cyclists and riders. The byway ends where US 58 crosses the state line beside Cumberland Gap National Historical Park, and the drive mapped here follows all of it, from the Tennessee line below Weber City to that last stretch by the park.

Plan a drive on Daniel Boone Heritage Trail → Drive this route in Road SortiesTurn-by-turn on iPhone · App Store

The drive our planner maps: 74 miles, about 1 hr 25 min behind the wheel.

Where to Stay along Daniel Boone Heritage Trail

2 campgrounds and RV parks sit within about 5 miles of Daniel Boone Heritage Trail.

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What is a State Scenic Byway?

State Scenic Byways are roads a state has formally recognized for their scenic, natural, historic or cultural value — each state's own curated collection of drives worth taking slowly.

← All scenic roads in Virginia