In today’s edition of RallyGrid’s Roads You Should Know, we bring you the Eye of the Dragon in Kentucky. Made famous by our friends at Man O’War Harley Davidson, this 27 mile loop is one of our absolute favorites east of the Mississippi. The incredible slate of eastern Kentucky roads you’ll drive along this route are just the start. As fun as these roads are to rip through, you might just want to take your time on this one considering all the amazing views offered up by the mountains, bridges, and landscapes along the way. Pro tip: Just search ‘Eye of the Dragon’ in the RallyGrid app to launch the pre-made Google Maps route.

This drive caresses Kentucky’s Red River Gorge Geological Area, which spans approximately 29,000 acres and is part of the Daniel Boone National Forest. By far, the coolest landmark you will see along this route is the Nada Tunnel. No, this isn’t a tunnel that hurts your feelings by delivering a ridiculously low valuation on your car. The Nada Tunnel (actually pronounced “Nay-duh” was constructed in the early 1900s by a local lumber company for that purpose alone. Coming in at 900 feet long, but only 12 feet wide and 13 feet high, it definitely isn’t a tunnel you’ll pass through at high speed.
While driving the Eye of the Dragon in Kentucky, you’ll also pass by the Natural Bridge State Park. You’ll need to stop and take a short hike, but the experience is definitely worth it. This natural sandstone bridge is 65 high and 78 feet long. The structure is super cool to see. And assuming you can get to it, you can even get up there and walk along it.
On the eastern edge of the loop, you’ll also have an opportunity to check out the famous Sky Bridge Trail. Head north up Sky Bridge Road off of Highway 715, continue past the Devil’s Canyon Lookout, and you’ll arive at the trailhead. The trail is a loop less than a mile in length and offers incredible views of the Sky Bridge itself. This area makes for a great rest stop during your drive.