Cherohala Skyway: The $100 Million Road That Started as a Wagon-Train Dare
The Cherohala Skyway is a 43-mile National Scenic Byway that climbs from the valley floor to overlooks above 5,390 feet, connecting Tellico Plains, Tennessee to Robbinsville, North Carolina through the Cherokee and Nantahala National Forests. It’s one of the great mountain rides in the Southeast — long, sweeping, high, and gloriously empty — but here’s the part almost nobody tells you: this road exists because of a joke.
In 1958, at a Kiwanis Club meeting in Tellico Plains, a local named Sam Williams — inspired by the TV western Wagon Train — half-jokingly suggested they organize a real wagon train over the mountains into North Carolina. Six weeks later, 67 covered wagons and more than 300 riders on horseback gathered at the state line and made the crossing. It became an annual tradition, and the ruts those heavy wooden wheels carved into the ridgeline traced the preliminary route for the highway you’ll ride today. Federal funding followed in 1962, bulldozers broke ground in 1967, and after 34 years of planning and grueling high-elevation construction, the Skyway finally opened on October 12, 1996 — at a cost of $100 million, earning it the title of North Carolina’s most expensive scenic highway.
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🇺🇸 That Red-White-and-Blue “Rocket Thrust”? It’s a Flag Ride.
Streaming off the back of the bike you’ll see what looks like a stars-and-stripes rocket trail. That’s a full-size American flag flying behind me — the 360° fisheye perspective stretches it out into that comet-tail look. I ran the Cherohala Skyway as a flag ride for our country’s 250th birthday, marking the semiquincentennial of the Declaration of Independence (1776–2026). So when the road opens up and Old Glory goes streaking out behind the tail, now you know why.
Route Stats at a Glance
- Length: 43 miles total ~23 miles in Tennessee on TN-165, ~18–20 miles in North Carolina on NC-143
- Endpoints: Tellico Plains, TN ↔ Robbinsville, NC
- Elevation: Rises from roughly 900 ft to 5,390 ft at the highest overlooks (over 4,000 vertical feet gained)
- Forests crossed: Cherokee National Forest (TN) & Nantahala National Forest (NC)
- Fuel & food: NONE for the entire 43 miles — no gas, no stores, no restrooms. Fill up first.
- Best surface: Long-radius sweepers built for momentum — Cherohala Skyway is a legendary sports-car and motorcycle road by happy accident
Why the Curves Are So Good (It Wasn’t On Purpose)
The name Cherohala is a portmanteau of the two federally protected lands it bridges — Cherokee National Forest in Tennessee and Nantahala National Forest in North Carolina. Building it meant blasting through solid rock at extreme elevation and dragging heavy machinery up near-vertical slopes to lay a smooth two-lane roadbed that climbs over 4,000 vertical feet. Because the crews prioritized long, sweeping, long-radius curves to help vehicles hold momentum on the steep grades, the road accidentally became a rider’s dream. Nobody set out to build a motorcycle mecca — the engineering just happened to produce one.
👆 See Me Pointing Up? Here’s What You’re Looking At
On the high North Carolina ridges near Robbinsville, watch for me pointing skyward at what look like odd, bare 40-foot poles beside the road. Those are flying squirrel bridges. When the highway was cut through the forest, the gap between the trees became too wide for the endangered Carolina Northern flying squirrel — which travels only by gliding tree to tree — leaving populations stranded on either side of the asphalt. Biologists and engineers installed three pairs of 40-foot wooden poles with diving-board-style platforms on top, giving the squirrels a high launch-and-landing pad to glide safely over the road. They sit up in the cold spruce-fir peaks, a climate that mimics the Canadian boreal forest these squirrels need. Blink and you’ll miss them — so when you see me point, look up.
Know Before You Go
There is no fuel and no food for 43 miles on the Cherohala Skyway. There are no gas stations, no stores, and no services anywhere on the Skyway itself. Top off your tank in Tellico Plains or Robbinsville before you commit to the crossing.
The weather up top does its own thing. The high ridges get cold, windy, and fogged in even in summer, and can turn genuinely dangerous with snow and ice in winter. Pack a layer you don’t think you’ll need, and check conditions before you head up — the valley and the summit can be two different seasons on the same afternoon.
Key Stops & Detours Worth Making
- Bald River Falls — a thundering ~100-foot waterfall just off the route on the Tennessee side, and one of the easiest big payoffs on the whole ride.
- Huckleberry Knob — a short 1.7-mile hike to an open meadow summit with 360-degree mountain views. The highest point in the immediate area and worth the boots.
- Joyce Kilmer Memorial Forest — a nearby protected old-growth forest with massive, centuries-old trees and an easy 2-mile figure-eight loop trail.
- Santeetlah Overlook — one of the highest-elevation pull-offs on the route, with wide valley views that make an easy, no-hike photo stop.
Where to Stay: Mountain Retreat, Tellico Plains
Since Tellico Plains sits right at the western end of the Skyway, it’s the natural basecamp for the ride — and if you want somewhere with real character to point the bike at when you’re done, we’ve stayed at Mountain Retreat & The Saloon Venue and it earns the recommendation. It’s the passion project of owners Richard and Antonio, who bought a forgotten mountain property, poured a year and a half of hard work into it, and brought it back to life without losing its original charm.
What you get: cozy, spotless short-term cabins (including the famous “Garage”), a general store, boiled peanuts at the Nut House, and some of the best sunrise and stargazing skies in the area thanks to almost no light pollution. It’s pet-friendly, so your four-legged riding companion is welcome too. We wrote up the full story and two ways to get there in our Mountain Retreat guide — how to get there, two routes, one perfect destination.
The CowFactor Ratings
— About as high as it gets in the Southeast. Over 4,000 vertical feet of climb to 5,390-ft overlooks, with real mountain weather to match.
— Strong on the Tennessee side thanks to Bald River Falls and the creeks feeding it, lighter up on the dry high ridges.
— Mostly deep national forest with little livestock; a little farmland down near the Tellico Plains end.
— Wild animals possible: this is black bear country through both national forests, with deer and other critters common at dawn and dusk. Ride alert.
Perfect For
- Riders who want long, flowing sweepers over tight technical hairpins
- Anyone pairing it with the Tail of the Dragon for a big two-road weekend
- Photographers chasing high-elevation overlooks and fall foliage
- Cool-weather escapes when the valleys are baking in summer heat
Pro Tips
- Fuel up first — seriously. 43 miles, zero gas. Don’t be the story other riders tell.
- Ride it early. Morning light on the overlooks is best, and you’ll beat the weekend traffic and RVs.
- Pack a layer. The summit can be 15–20 degrees cooler and socked in with fog while the valley is clear.
- Watch for the squirrel poles near Robbinsville — and check your mirrors before you slow down to gawk.
📥 Download the Cherohala Skyway GPX route file
Filmed in 360° on the Insta360 X4 and X5. All footage and photography © SugarFree Productions LLC.
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