Kentucky

Eastern Kentucky is one of the most underrated riding regions in Appalachia. The sandstone canyon country of Red River Gorge packs narrow forest pavement, natural arches, and a one-lane 1910 railroad tunnel into a compact loop, while the surrounding hills hide some of the tightest paved roads in the state. The Red River Gorge Scenic Byway is the classic introduction, the Eye of the Dragon (KY-715) is its technical heart — roughly 25 miles of narrow cliff-line pavement with blind crests — the Hillbilly Triangle stitches the gorge into a roughly 260-mile sport-touring loop through bluegrass horse country, and the Country Music Highway (US-23) runs a faster, more open 144 miles down the state's Appalachian spine. There's a route here for every style of bike.

Kentucky's best riding concentrates where the bluegrass plateau breaks apart into Appalachian canyon country. Red River Gorge is the centerpiece — a sandstone canyon system in Daniel Boone National Forest littered with cliff lines, rock shelters, and natural arches — and the roads that thread it were never built for through-traffic, which is exactly why they ride the way they do. East of the gorge, US-23 follows the coalfield valleys down the state's Appalachian edge, a designated National Scenic Byway that honors the region's country music heritage from Loretta Lynn to Chris Stapleton.

Matching the Route to Your Bike

The four routes on this page cover distinct styles of riding:

• Pavement, technical focus: The Eye of the Dragon (KY-715) is Kentucky's most demanding paved road — roughly 25 miles of narrow, 1.5-lane pavement along the gorge's cliff lines, with blind crests and tight switchbacks. It rewards lighter, more flickable bikes and a patient pace.
• Pavement, scenic loop: The Red River Gorge Scenic Byway (KY-15, KY-77, KY-715) is the roughly 40-mile sampler — Nada Tunnel, Sky Bridge, and constant sandstone scenery. Any bike works if you respect the narrow lanes.
• Sport-touring distance: The Hillbilly Triangle is a roughly 260-mile loop from Mount Sterling combining KY-11, KY-77, KY-715, US-460, KY-36, and US-60 — gorge backroads on one leg, horse country on another. It's a multi-road loop with no single designation, so plan the legs before you set out.
• Open-road touring: The Country Music Highway (US-23) runs about 144 miles from Greenup to Whitesburg via Ashland and Pikeville — mostly fast, open highway through ridge country, well suited to baggers and anyone covering ground.

Hazards and Local Knowledge

The gorge roads are narrow enough that oncoming pickups and slow-moving sightseers are the main hazard, not the corners themselves. The Nada Tunnel is single-lane and unlit with a wet, gravel-strewn floor — treat every entry as blind. Cell coverage is unreliable through the gorge and across much of eastern Kentucky, so download offline maps. Deer are a constant dawn-and-dusk concern, and gravel washes onto the smaller connecting roads after heavy rain.

Planning Notes

Slade is the natural base for gorge riding — fuel, food, and lodging, with Miguel's Pizza as the traditional rider stop — and Stanton works as a backup; fuel up before heading into the gorge itself, since services inside are essentially nil. The Red River Scramble, a grassroots adventure rally based near Beattyville south of the gorge, draws a large dual-sport and ADV crowd each year (the 2026 edition runs in early October) — book lodging early that weekend or use the rally as an anchor for your own trip. Dual-sport riders should also look at the Kentucky Adventure Tour, a roughly 1,000-mile mixed-surface loop around Appalachian Kentucky whose northern sections are accessible from Slade.