Historical rendering of Daniel Boone and the frontier party blazing their way along the Wilderness Road

Historical Rendering of Daniel Boone Along the Wilderness Road

One of the nation’s most historic routes, the Daniel Boone Wilderness Trail was blazed by the legendary frontiersman in 1775 from the Long Island of the Holston at what is now Kingsport TN, through the Cumberland Gap of Virginia into Kentucky.  It would become the route for thousands of settlers to the western frontier.

Long before Columbus discovered America, the Wilderness Trail was a major link in the trail systems of the Indians on the North American continent, used for commerce and raids.  Gabriel Arthur, a young indentured servant, was the first of record to travel the route and see the Cumberland Gap, a natural break in the mountains.  Arthur was sent along the trail in 1674 by the Shawnee Indians to secure a trade agreement with settlers.  The next recorded man to see the Gap was Dr. Thomas Walker in 1750.

The most daring effort to colonize the rich lands of the Kentucky River area were those of Colonel Richard Henderson, a Superior Court judge of North Carolina.  Henderson decided the best way to secure the area was to deal directly with the Cherokee Indians.  He discussed plans with friends, and they formed the Transylvania Company and solicited the assistance of Boone in negotiating with the Indians and blazing the trail.

On March 10, 1775, Boone led his 30 trail blazers from Long Island of the Holston to cut the trail through some 200 miles of wilderness northwest through the Cumberland Gap and into Kentucky.

Thanks to the Daniel Boone Wilderness Road Trail Association, today, travelers can follow the Wilderness Trail as closely as possible along the original route.  Several historical stops are available along the route, and it makes a great day-long road trip through the scenic rolling hills and valleys of Scott County, VA into Lee County, VA to the Cumberland Gap into Kentucky.

Travelers may begin their journey at any juncture along the Wilderness Road.  Some of the more significant stops are listed below.  For detailed map:

Netherland Inn, Long Island of the Holston, Kingsport, Tennessee

Long Island on the Holston, or Hogoheegee River was the sacred treaty ground to the Cherokee.  It is the western terminus of the Reedy Creek Road, which carried the Great Warrior’s Path from Bristol to Kingsport. The Netherland Inn was strategically located in King’s Port and served as a way station for both river and road travelers.  Visitors can access the Long Island of the Holston via a swinging bridge, located on the Greenbelt walkway across from the Netherland Inn.  On the island, visitors can see the monument erected by the Cherokee nation on land ceded to them in commemoration of the United States Bicentennial.  The stone in the monument was brought from the Qualla Reservation at Cherokee, North Carolina.

Long Island of the Holston Marker

Cherokee Nation Marker at Long Island of the Holston

Anderson Blockhouse Site, Carters Valley, Scott County, Virginia

The historic marker indicates the original location of the John Anderson Blockhouse.  Anderson built his blockhouse on the knoll here sometime before 1775. (A replica of the John Anderson Blockhouse was constructed at Natural Tunnel State Park, Duffield, VA.  Generally open Saturday and Sunday, May through October, it is currently closed due to COVID-19.  Visitors can drive up and visit the grounds.)

A blockhouse was a specialized log cabin built of squared logs, and with an upper story that extended out overhanging the walls of the lower structure.  The squaring of the timbers made a tight fit, which left no space for an adversary to shoot through into the interior of the structure.

Since the favorite way to get someone who was barricaded within a log cabin to come out was to set fire to it, the overhanging upper story afforded the opportunity to shoot down on anyone attempting to set the lower building on fire.  Blockhouses were used as fortified strong points by the military all across the Eastern North America.

The Anderson Blockhouse functioned as a gathering spot for pioneers, who would wait at the Blockhouse until enough “guns” had gathered to make the trek through Indian territory.  The Blockhouse was the last contact with the Holston Settlements.

After gathering his 30 ax men at Fort Patrick Henry, it was at the Blockhouse that Boone began to blaze the trail into Kentucky.  The trail went north past the Blockhouse on state route 606 to the ford just upstream from the present swinging bridge.  The swinging bridge is still maintained by the Virginia Department of Transportation (VDOT), and visitors are encouraged to meander out on the bridge.

Moccasin Gap, Gate City, Virginia

Moccasin Gap in Clinch Mountain is one of two ground level water gaps leading from the western reaches of the Great Valley of Virginia into the interior of the Alleghenies, the other being the Narrows of the New River.

The two main trails of the central Appalachians joined for a short distance to make the passage through Moccasin Gap.  The most important one was the Great Warrior’s Path, or the Wilderness Trail, or alternately the Daniel Boone Wilderness Trail.

This area was of great significance during Indian times because it was the main trail connecting the Cherokee Country with that of the Shawnee in Ohio.  This last trail ran from the Smokies through Moccasin Gap to Big Stony Creek to High Knob, Pound Gap, Elkhorn Creek, The Big Sandy River, and across the Ohio River.

Daniel Boone, Virginia, Scott County

Hob Nob Restaurant

Hob Nob Drive-in Restaurant

This railroad yard and the community that surrounds it is the only place in Virginia named after Daniel Boone.  This is the original Daniel Boone Wilderness Trail, and Boone reportedly drank from a spring in this area.  Today, this area is more famous as the home of the Hob Nob, an iconic restaurant that has been in the same family for more than 60 years.  It is famous for its diner fare, in particular the soft-serve ice cream cones.

Clinchport, Virginia and Stock Creek

Cinchport was the head waters of flat boat navigation on the Cinch River, just as Kingsport was on the Holston.  Not only did pioneer loggers build massive log rafts here in the winter to catch the spring tide to float their logs to mills at Chattanooga, but settlers farther up the Clinch would bring produce downstream in dug out canoes called bateaux.  Clinchport was the region’s point of entry into the Tennessee River System.  The Wilderness Road followed Stock Creek from here.

Natural Tunnel State Park, Duffield, Virginia

Natural Tunnel is a great spot to stop, get out and stretch your legs.  Although the Visitor Center is not open to the public now, the chairlift down to the bottom of the Tunnel is currently available Friday through Sunday.  Ride the chairlift down where you can take the boardwalk out to the mouth of the 850-feet long tunnel.  Tall as a ten-story building, the limestone cave within the tunnel was carved out thousands of years ago by Stock Creek.


Replica of John Anderson Wilderness Road Blockhouse

Wilderness Road Blockhouse Exploration Station, Natural Tunnel State Park, Duffield, Virginia

Located within Natural Tunnel State Park, the Wilderness Road Blockhouse is a replica of the original John Anderson Blockhouse that stood on now Carter’s Valley Road and served as a gathering point for pioneers. Those making their way westward would gather at the Blockhouse until there were enough “guns” to make the trek through Indian territory westward to Kentucky.  The Blockhouse is currently closed to visitors due to COVID-19, but travelers may still stop and walk around the grounds.

Daniel Boone Historical Marker, Duffield, Virginia

One of the few remaining Daniel Boone Historical markers in existence.

Kane Gap, Duffield, Virginia

This natural notch was a welcome sight to travelers on the Wilderness Trail.  It was through this Gap that countless thousands trudged as they made their westward.  Accessed via Fraley Avenue, Duffield, this is the only trail where you can actually walk in the footsteps of famed frontiersman Daniel Boone.  The trail is part of the Daniel Boone Birding and Wildlife Trail.  Managed by the Jefferson National Forest Service, the trail is moderate to difficult, but is worth the climb to the Gap.  Just before reaching the Gap, visitors will see the “pioneer hotel” recorded in many journals.  This large rock outcrop served as a shelter to the thousands before they crossed down into the valley below.

Daniel Boone Wilderness Road Interpretative Center, Duffield, Virginia

A satellite location of Natural Tunnel State Park, the Center is currently open Fri.-Sun., 10 a.m.-6 p.m.  Admission is free.  Here visitors learn the important role the Wilderness Road played in American’s westward expansion.  The center offers a glimpse of the rough, unforgiving terrain early settlers traversed on their way to Kentucky.  The museum focuses on the portion of the trail from Sycamore Shoals in Elizabethton, Tennessee to the Cumberland Gap and the brave men, women and children who traveled the trail.  There are several hands-on exhibits, such as striking flint and steel to get a spark.

Powell Mountain Overlook, Duffield, Virginia

Regardless of the season, the Powell Mountain Overlook always delivers an amazing view.  Located between Duffield and Stickleyville, Virginia, the Overlook offers a spectacular view down into the valley below and is a favorite stop along the Wilderness Road.

Stickleyville School, Stickleyville, Virginia

The school stands on or near the site of the massacre of James Boone, Daniel’s son.  At the time, the Boones were migrating to Kentucky and James had gone ahead along with several others, notably, Henry Russell. According to accounts of the massacre, “wolves” howled all night around the camp.  At dawn, a mixed party of Shawnee and Cherokee Indians attacked and shot James Boone and Henry Russell, through the hips so that they could not escape.  The pair were then tortured with knives and then killed.  Boone is said to have asked a Shawnee Indian, Big Jim, who Boone knew from visits to the Boone family homestead in North Carolina, to kill him.  Russell was reportedly clubbed to death and his body shot full of arrows.

Jonesville, Virginia

Mumps Fort stood at the top of the hill where the current courthouse is located today.  The Fort was built by William Mumps in 1775 in a community known then as Glade Spring or Sinking Springs.  Mumps Fort abandoned in 1776 at the outbreak of the Cherokee War.  The garrison was then repositioned at Fort Blackmore in Scott County, Virginia.

White Cliffs, Ewing, Virginia

White Cliff Rocks, Ewing,  Virginia

White Cliff Rocks, Ewing, Virginia

The white rock cliffs atop Cumberland Mountain were among the most commonly mentioned geographic features recorded in the journals of the emigrants along the entire length of the Trail.  The pioneers seemed to take the cliffs as a hallmark of the wonderful new land that they were claiming as their own.

The term Cumberland seemed to ring in the souls of the pioneers as the name of the port-of-entry into the Promised Land.  The Cumberland Mountain guided them on their way until they reached Cumberland Gap, which was the gateway to Eden.  From there they traveled across the Cumberland Valley to the Bluegrass of Kentucky.

Wilderness Road State Park, Ewing, Virginia

The Wilderness Road State Park offers picnicking, hiking and nature and living history programs.  Visitors can enjoy the visitor center, home to a theater showing an award-winning docudrama, “Wilderness Road, Spirit of a Nation.”  The center also has a frontier museum and a gift shop with unique regional gifts.  The park features the reconstructed Martin’s Station, an outdoor, living history depicting life on Virginia’s 1775 frontier.  Guests can also enjoy the park’s picnic shelters, nature play-scape, ADA-certified playground, sand volleyball court and horseshoe pits.

Visitors can hike, bike or horseback ride on the 8.5 Wilderness Road Trail linking the park with more than 50 miles in the Cumberland Gap National Historical Park.

Cumberland Gap National Historical Park, Middlesboro, Kentucky

Cumberland Gap National Park

Cumberland Gap National Park

Cumberland Gap National Park is located at the crossroads of Kentucky, Tennessee and Virginia and creates a natural break in the Appalachian Mountains.  The Cumberland Gap Visitor Center features a museum with interactive exhibits about the Gap’s role as a transportation corridor, and also features the Cumberland Crafts gift shop, which houses juried wares from crafters throughout Appalachia.

The park covers 24,000 acres and is among the largest national parks in the eastern United States.  Stretching about 20 miles, the park runs along the Cumberland Mountains.  It includes 24 known cave features, ranging in size from around 20 feet to more than 16 miles in length.  There are also a large number of cliff systems in the park, the most prominent of which is the 500 feet cliffs of White Rocks, which is located in the eastern portion of the area.  At the northeastern end, the park lies adjacent to the Sillalah Creek Wildlife Management Area and Martin’s Fork Wildlife Management Area and State Natural Area.

Driving the entire Wilderness Road Trail can be done in one full day.  Conveniently located along the way are several places to dine, including Campus Drive-in and Family Bakery, Gate City; the Hob Nob, Daniel Boone; Chubeez, Duffield; A Better Burger, Jonesville; and Dutch Treat, Rose Hill; as well as national chain fast food restaurants.

For lodging convenient to the Wilderness Trail, visitors have the option of Roberts Mill Suites and Estilville Bed & Breakfast, Gate City; Appalachian Mountain Cabins and PapPaw’s Cabin, Duffield; Valliee Farm Farmhouse, Stickleyville; and Wilderness Road Bed & Breakfast, Ewing.  Camping is available at both Natural Tunnel State Park and Cumberland Gap Wilderness Road Campground.


From cool, sparkling mountain creek trails to high-country scenic vistas, Scott County, Virginia and its surrounding counties offer the perfect hike to suit any adventurer’s desire or ability.  All of the hikes listed below, with the exception of the Chief Benge Scout Trail, can be completed in a day and provide a variety of hiking options.  Many of these trails, like Kane Gap and the Sand Cave, are also suitable for horseback riding.

Bark Camp Lake

Fall Colors at Bark Camp Lake

Bark Camp Lake—Bark Camp Lake, Scott County

A 3.5-mile loop trail that circles Bark Camp Lake is one of the easiest and most scenic fall hikes.  The colors will not disappoint, and the lake is a prime spot for anglers and kayakers. Located in the Jefferson National Forest, picnic facilities are available.  Bathtub facilities are currently closed.  Bark Camp is located between Dungannon and Tacoma in northern Scott County.  Take Alternate 58 to Tacoma, then Route 706 to Route 822; then U.S. Forest Development Road (FDR) 993 to the lake.

Chief Benge Scout Trail—High Knob Land Formation, Wise and Scott Counties

Born to a Scots-Irish trader named, John Benge, and a Cherokee woman, Chief “Bob” Benge stood out physically because of the red hair inherited from his father.  In his 20s, Benge joined forces with the Shawnee band of the Chiksika. He was well-known for his raids against American settlers as far north as the Ohio River, deep into Southwestern Virginia, North Carolina, Georgia and South Carolina.  The trail is named after him because this is the approximate area where Benge was killed by militia leader Vincent Hobbs Jr.

At almost 19 miles, this is the longest hiking trail in the region.  The trail creates a tour of the High Knob high country, starting at the High Knob Lookout Tower near Norton and ending at the Hanging Rock Recreation Area just north of Dungannon.  The Chief Benge trail passes everything from sweeping, 360-degree vistas of five states atop the High Knob Fire Tower to rugged mountain stream gorges, sluices and waterfalls, two high-elevation lakes, and dense hardwood forests in between.

Devil’s Fork Trail Loop—Dungannon, Scott County

The Devil’s Fork Trail Loop is a seven-mile, round trip that accesses the famed Devil’s Bathtub.  The trail can either be followed in its entirety loop-wise or broken down for easier access.  Once you cross the first creek, you will come to a “T” in the trail.  Here you have the option of taking the trail to the right, which is four miles with no creek crossings or the trail to the left with 13 creek crossings to access the Devil’s Bathtub.

Either way, this is technical terrain.  Hikers are advised to check weather conditions before accessing the trail as water levels could be higher following significant rainfall.  Hikers are advised to avoid parking in the small lot at the trailhead to the Devil’s Bathtub.  The access road has become rutted and impassable except for high vehicles.  Instead, please use the new parking lot located at 312 High Knob SC, Dungannon, VA 24245.

Falls of Little Stony—Dungannon, Scott County and Coeburn, Wise County

Make sure to pack a camera for the hike to the Falls of Little Stony.  The Little Stony National Recreation Trail is a 2.8-mile trail with an upper trailhead at the Falls of Little Stony Creek and a lower trailhead at Hanging Rock Picnic Area.

Falls of Little Stony

This trail follows Little Stony Creek through a 400’ deep and 1700’ wide gorge.  Large outcrops, rock ledges and boulders form the scenic edges along Stony Creek. In some areas, hikers will need to climb around/over boulders and large rocks to remain on the trail.  A scenic 27’ waterfall, along with two smaller waterfalls, gives this site its name.

With several covered shelters, Hanging Rock Picnic area is a great spot to enjoy a picnic lunch.  Shelters are open: bathroom facilities are closed.

Flag Rock—High Knob Land Formation, Wise County

This 1.1-mile trail climbs almost a thousand feet one-way as it travels from Legion Park to Flag Rock Recreation Area.

Guest River Gorge—Jefferson National Forest, Wise County

A Rails-to-Trails path, this 5.8-mile gravel footpath travels along the Guest River to its confluence with the Clinch River.  The trail follows the Guest River as it meanders by eight branches and creeks and terminates at the Guest River’s confluence with the Clinch River.

This scenic trail passes through riparian woodlands, creekside bottoms, 300-million-year-old cliff lines and rock outcrops.  An abundance of wildlife is easily viewed along this trail, with spectacular migration along this riparian corridor in spring and fall.  Keep an eye out for giant snapping turtles and various salamanders.  Also great for fishing.

Kane Gap—Duffield, Scott County

This historic footpath is the only trail today where you can walk in the actual footsteps of famed frontiersman Daniel Boone.  It was up this mountain and through Kane Gap that Boone and his 30-axe men blazed the Wilderness Road Trail, opening the way for thousands of migrants to make their way west.

The Daniel Boone Wilderness Trail Association has marked Boone’s historic trail, where you can still see the pioneer “hotel” that housed thousands crossing over into Wallen’s Valley and then onward to Kentucky.  Once used as a mail route, the trail is fairly easy to traverse but includes a somewhat step zig-zag ascent to the top of the Gap.  Most of the trail is surrounded by habitat of Appalachian mixed forests as well as remnants of old orchards.

Natural Tunnel State Park—Duffield, Scott County, Seven Trails

  • Purchase Ridge, 2.07 miles, moderate
  • Stock Creek, 1.03 miles, moderate
  • Virginia Birding and Wildlife, 0.7 miles, moderate
  • Tunnel Hill, 0.54 miles, moderate
  • Cabin, 0.5 miles, easy
  • Lover’s Leap, 0.36 miles, moderate
  • Gorge Ridge, 0.27 miles, moderate
  • Tunnel, 0.27, difficult
  • Carter Log Cabin, 0.13, easy

This following link provides detailed description on how to link the Natural Tunnel Trails for a challenging day hike.

Sand Cave Ewing Virginia

Sand Cave, Ewing, Virginia

Sand Cave—Ewing, VA, Lee County

Tucked away in the Cumberland Gap National Park, hikers and horseback riders will discover a ceiling of gold, red and green, eroded rock forms and photo ops to cherish.  Access to this gem is through Thomas Walker Civic Park in Ewing.  A 3.9-mile hike brings visitors to the entrance of this natural wonder.  Continuing along this trail, leads to White Rocks (5.2 miles) where hikers and equestrians can view three states—Virginia, Kentucky and Tennessee.  Horses are welcome and there is ample trailer parking at the trailhead.

Several overnight options are available for visitors wanting to hit more than one hiking area.  Depending on personal needs, you can either grab a tent and sleeping bag and “rough it” at camping accommodations within Natural Tunnel State Park or pile up along the banks of the Clinch River at either SomeThing Squatchy or Camp Clinch.  All offer primitive camping and RV hook-ups.  Natural Tunnel even has primitive Yurts for rent.

After a day-long hike, those who prefer a nice long soak in a Jacuzzi tub are encouraged to make Appalachian Mountain Cabins home base for their foray into the wilderness. Locally-owned and operated, Appalachian Mountain Cabins features four cabins with sleeping accommodations for two to eight persons.  Cabins are fully furnished and include satellite television and free WiFi.

Scott County is home to several locally-owned iconic restaurants including the Hob Nob, Teddy’s Restaurant, Chubeez, Front Porch Store & Deli, The Redstone and Campus Drive-in.  No trip to Scott County is complete without a stop at The Family Bakery in downtown Gate City.  Voted “Virginia’s Best Bakery,” the bakery features amazing cupcakes and lunches that are perfect to take out for a picnic lunch.

For more information or assistance planning your hike, please call Scott County Tourism at 423-863-1667.

Continue the journey along the Wilderness Road by visiting the new Daniel Boone Wilderness Trail Interpretative Center, located in Duffield, Virginia.  Daniel Boone Interpretative Center

The new center overlooks Kane Gap–a visible representation that shows the path settlers once toon on their westward journey.  A satellite location of Natural Tunnel State Park, the Daniel Boone Wilderness Trail Interpretative Center is a multi-purpose facility with a large conference room, library and museum.  The center focuses largely on the story of the Wilderness Road from Sycamore Shoals to Cumberland Gap.  The ultimate goal is to educate visitors on the importance of the Wilderness Road and the key role it played in westward expansion.

At the center, explore the interactive museum, participate in a scheduled program and visit the gift shop for souvenirs and additional information about the area’s history.  The center is the perfect location to schedule a field trip or reserve the conference room for a meeting or special event.

Winter hours of operation are Friday through Monday, 10 a.m. to 6 p.m.  Free.  Located at 371 Technology Trail, Duffield, Virginia.

Call 276-431-0104 for more information.


Estillville Bed & Breakfast, Gate City
Falls of Little Stony