Crooked Road
Caravan, Part 2.

Highways · Crooked Road Caravan 2026 · Part 2

Trip 03 · Fall 2026 · Part 2
A wide view of our second base camp at golden hour: Airstream trailers and trucks parked on both sides of a curving gravel lane, with green grass, fall-colored trees and a paved road at either edge

Our second base camp.

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This is Part 2 of our first Airstream Caravan on Virginia's Crooked Road. Part 1 covers our first base camp. This part starts on moving day.

We made the three-hour, 144-mile drive to our second base camp and got settled in for the day. There wasn't much scheduled, since everybody arrived at different times. The caravan left the first base camp in groups of three, about 20 to 30 minutes apart. We were fortunate to be in the first group, so we arrived early and had plenty of time to set up and relax.

Our Airstream parked at an angle on a gravel site under trees, with the awning out, camp chairs, and a rug with a dog bed in front of it

Our rig, set up on arrival day.

The base camp occupies two sections of the campground. The short rigs, 25 feet or less, are in the main campground with the bulk of the caravan, and the larger rigs (ours and about seven others) are on the other side of the campground, in spots better suited to our size. I actually think our sites are much better. They're far more private, which we like, and it's only a three-to-five-minute walk across to the main caravan group.

Day 6 ·

Day 6: Cumberland Gap, Natural Tunnel and Bluegrass at Camp

The second day had some scheduled activities. However, Heather and I decided to break away from the group and do some exploring on our own. The dogs had been cooped up in the trailer, and we wanted to get them out to stretch their legs.

Cumberland Gap and Pinnacle Overlook

Instead of going to a museum, we made the 50-mile trip up to Cumberland Gap National Historical Park. We drove up to Pinnacle Overlook and walked out to the viewing spot overlooking the countryside.

Pinnacle Overlook sits at about 2,440 feet, with views across Kentucky, Tennessee and Virginia. From the park's visitor center it's a four-mile drive up a two-lane road, followed by a short walk of about 150 yards on a paved path. Dogs are allowed there, which was good news for ours.

Where
Four miles up Pinnacle Road from the park's visitor center, 91 Bartlett Park Road, Middlesboro, Kentucky
Elevation
2,440 ft
The walk
About 150 yards on a paved, accessible path
Park info
nps.gov/cuga
Pinnacle Overlook, Cumberland Gap National Historical Park Open the full map Get directions
A wide view from Pinnacle Overlook over forested ridges and a valley town, with a stone retaining wall and an interpretive sign at the right edge of the viewing platform

The view from Pinnacle Overlook.

Cumberland Gap is the natural doorway through the mountains that the Wilderness Road passed through. Daniel Boone and a crew of axmen cut that trail in 1775, starting at the Long Island of the Holston in present-day Kingsport, Tennessee, and more than 200,000 pioneers are said to have followed it to Kentucky.

Paint on the pavement marks the state line, with the word Kentucky on one side and Virginia on the other

A painted line on the pavement marks the Kentucky–Virginia state line.

We walked around a bit with the dogs, who were happy to get out and stretch their legs and explore the new area. There were lots of good smells for them.

There were also a lot of little critters that kept them occupied. Squirrels and chipmunks seemed to run across the trail in front of them, almost as if they were teasing the dogs.

Natural Tunnel State Park

Our campsite had very high water pressure, which burst one of our hoses, so we took a small detour to Lowe's to grab a new hose before returning to camp. Once we had the new fresh water hose, I got out our pressure regulator and connected it, just in case. The water pressure was a minor inconvenience, but it's easy to see why a regulator is worth having: RV plumbing is generally meant for about 40 to 50 psi, and a campground spigot can deliver far more.

We left a short while later for Natural Tunnel State Park, where we took the chairlift down to the bottom and made the short walk to the tunnel.

Where
Scott County, Virginia, about 13 miles north of Gate City
Opened
1971
The tunnel
About 838 feet long and up to 80 feet high
Chairlift
The only one in Virginia's state park system
Natural Tunnel State Park: the visitor center and the tunnel floor Open the full map Get directions Park website
The wood-sided chairlift station at Natural Tunnel State Park, with a covered deck, a parking lot in front and wooded hills behind
The chairlift station at the top.
A wooden boardwalk running beside a gravel railbed below a tall limestone cliff, with autumn trees along the right side
The boardwalk at the bottom, below the limestone cliff.

The tunnel is a natural passage through a ridge in Scott County, carved out of limestone and dolomite over more than a million years as groundwater dissolved the rock and Stock Creek was diverted underground to keep wearing it away. It's about 838 feet long and up to 80 feet high and 200 feet wide. William Jennings Bryan called it the "Eighth Wonder of the World," and Daniel Boone is said to have been the first European to see it. The park was created in 1967 and opened to the public in 1971.

The trains came in the 1890s. The South Atlantic and Ohio Railroad built track through the tunnel in 1893, and the first train ran through in 1894. Norfolk Southern operates the line today, with CSX using trackage rights, and the trains that use it now carry coal.

Railroad tracks curving along a limestone cliff toward the dark mouth of Natural Tunnel, with a wooden fence and a Bruce Wingo Observation Area sign on the left
The tracks run along the cliff toward the tunnel, past the Bruce Wingo Observation Area.
The boardwalk and railroad tracks below a pale limestone cliff, with the tunnel entrance in the shadows beneath the rock and autumn trees on either side
The tunnel mouth under the cliff, with the boardwalk beside the tracks.
Dan in a dark cap and glasses and Heather in a pink top, smiling close together in a selfie in front of a railroad track that runs into a small tunnel under a rock cliff, with green trees and a No Trespassing sign at the right

Heather and me at Natural Tunnel.

The Legend of Lover's Leap

We wanted to walk the Lover's Leap Trail, but we were running out of time. It's still worth mentioning, because the legend is the one most closely tied to Natural Tunnel. As it's told, a Cherokee maiden and a Shawnee warrior who had been forbidden by their tribes to marry jumped to their deaths together from the highest pinnacle above the tunnel, and the cliff has carried the name ever since. The trail to the overlook is about 0.4 miles.

The story isn't unique to Virginia. Lover's Leap is one of the most common place names in the country, and the tale of lovers kept apart who choose to jump together is told at cliffs all over the continent. Mark Twain joked that there were fifty Lover's Leaps along the Mississippi alone, and another Virginia version is told in Patrick County. Whether or not it happened here, a cliff high above a tunnel carved by water is a fitting place for the legend.

Where
Lover's Leap Overlook, Natural Tunnel State Park
The trail
0.4 mi
The legend
A Cherokee maiden and a Shawnee warrior
The view
A bird's-eye look down at the tunnel
Lover's Leap Overlook, Natural Tunnel State Park Open the full map Get directions

The Wilderness Road Blockhouse

Afterwards, we did some more exploring around the blockhouse at Natural Tunnel State Park before returning to the campsite to prepare for dinner.

The Wilderness Road Blockhouse is a replica of the blockhouse John Anderson built in 1775 near Moccasin Gap, at the edge of the Holston settlements. For years it was a place where travelers gathered before setting out on the Wilderness Road to Kentucky, and it stood until a fire destroyed it in 1876. It's the same road that ran through Cumberland Gap, which we'd looked down on that morning, and the park hosts Revolutionary-era reenactors here each year.

A log blockhouse with a hip roof and stone chimney on a grassy hilltop, with a split-rail fence in the foreground and distant mountains behind it

The upper story overhangs the lower one, with small square firing ports in the logs.

The park's sign explains why blockhouses were built the way they were. The second story extended past the walls below, with firing ports cut into the floor so defenders could shoot down at anyone close to the walls. Fireplaces and chimneys were built inside so attackers couldn't remove the chimney and climb in through the fireplace. The logs were squared and fitted tightly, because bullets could pass through the chinked gaps in an ordinary log cabin, and small rectangular firing ports replaced windows so defenders could shoot in any direction without being exposed. According to the sign, no two blockhouses looked identical.

The Wilderness Road Blockhouse interpretive sign at Natural Tunnel State Park, with a pencil drawing of the log blockhouse beside text about how frontier blockhouses were built

The park's sign on the Wilderness Road Blockhouse.

The sign also quotes the journal of William Brown, who wrote that his party waited near two weeks at the blockhouse for company before setting out into the wilderness with 12 men and 10 guns.

A panoramic view across a mown grassy hilltop toward rolling green hills and distant blue mountains under a clear sky, with a long dark shadow stretching across the grass in the foreground

The view across the hills from beside the blockhouse.

Where
Wilderness Road Visitor Center, beside the picnic area in Natural Tunnel State Park
Original built
1775
Original burned
1876
Living history
Revolutionary-era reenactors visit each year
The Wilderness Road Blockhouse, Natural Tunnel State Park Open the full map Get directions

Barbecue and Bluegrass

Tonight's dinner was catered barbecue, which was actually very good and, after a full day, a very welcome meal. After dinner, we were treated to some live bluegrass music from the Lonesome Pine Bluegrass Band, a local band well known for its good music. After the show, it was time to settle in for the night and prepare for the next day's activities.

A bluegrass band playing in front of a white pickup truck at the campground while an audience sits in camp chairs on the gravel in front of them, with trees behind

The Lonesome Pine Bluegrass Band playing at camp after dinner.

Background from Virginia State Parks (its Natural Tunnel guide), Wikipedia's articles on Natural Tunnel State Park, Lovers' Leap and the Wilderness Road, the Crooked Road's blockhouse listing, the National Park Service and the blockhouse sign at the park. Water pressure guidance from RV Lifestyle and Winnebago.

Part 2 FAQ

What is Natural Tunnel State Park?
Natural Tunnel State Park is a Virginia state park in Scott County built around a natural tunnel about 838 feet long and up to 80 feet high, carved through a ridge by groundwater and Stock Creek over more than a million years. A railroad has run through it since 1894, and a chairlift and a boardwalk lead visitors down to the tunnel.

Can you see three states from Pinnacle Overlook at Cumberland Gap?
Yes. Pinnacle Overlook, at about 2,440 feet in Cumberland Gap National Historical Park, has views of Kentucky, Tennessee and Virginia. It's a short walk from the parking area on a paved path, and dogs are allowed there.

What is the Wilderness Road Blockhouse at Natural Tunnel State Park?
It's a replica of the log blockhouses the Holston Militia manned on the Virginia frontier, modeled on the John Anderson Blockhouse of about 1775. It sits on a hilltop in the park, which hosts Revolutionary-era reenactors there each year.

What is the legend of Lover's Leap at Natural Tunnel State Park?
As the legend is told, a Cherokee maiden and a Shawnee warrior who were forbidden by their tribes to marry jumped to their deaths from the highest pinnacle above the Natural Tunnel. The park's Lover's Leap Trail runs about 0.4 miles to an overlook above the tunnel.

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