One of our most technical trails, it boasts 94.1 miles (2.3 hours) of curves, switchbacks and crosses 2 state lines (KY and TN). Starting in Middlesboro, Kentucky, the only city in America built in a meteorite impact crater (3.6 miles in diameter), and the childhood home of actor Lee Majors- Astronaut Steve Austin, aka The Six Million Dollar Man, riders and drivers are immediately greeted by the Cumberland Gap Tunnel. Coming in at 4,600 feet long the tunnel is a symphonic dream-let’s hear those pipes! Passing under Kentucky, Tennessee and a sliver of Virginia, the trail sweeps out to Jellico, TN before heading back to Crater Town. Minutes away is Cumberland National Historic Park, home of The Pinnacle Overlook, Indian Mountain State Park and Pine Mountain State Park. For more info, see the What’s Around link on the App.