One of the best things about the Smoky Mountain H.O.G. Rally was the guided ride lineup, and for this day we picked a route that combined history, mountain roads, and a little dark humor. The destination was Brushy Mountain State Penitentiary, and the road that followed was the Devils Triangle—a combination that made this one of the more memorable days of the trip.

Brushy Mountain State Penitentiary

The group ride out to the prison went smoothly, which is not always guaranteed on larger guided rides. Brushy Mountain State Penitentiary opened in 1896, closed in 2009, and was once known as the “End of the Line” for Tennessee inmates. It also happened to be one of the rally’s challenge coin stops, which made it an easy addition to the route. Unfortunately for me, it is no longer accepting inmates, so Debbie had to come home with us. Brush Mountain is not the first prison to reject her; I tried at Alcatraz and the West Virginia Penitentiary. I even tired the Tran-Allegheny Lunatic Asylum too.

***If you like prison-themed or haunted motorcycle stops, related posts on the West Virginia Penitentiary ride and the Trans-Allegheny Lunatic Asylum ride make good follow-up reads.***

Why the Devils Triangle gets your attention

From the prison we rolled straight into the Devils Triangle. At roughly 44 miles, it is not the longest ride in the region, but it can feel every bit as demanding as more famous roads. Steep drop-offs, rougher pavement, narrow lanes, rock walls, and battered guardrails give the route a rawer personality than the more polished reputation of better-known Tennessee motorcycle rides.

We made it through without incident, although the road did throw in a few bonus challenges for good measure. An excavator was working in the roadway (and not properly marked either), also, a bit further along, a downed tree partly blocked one lane just after a turn. That kind of unpredictability is part of what gives the Devils Triangle its reputation among riders looking for a more rugged Smoky Mountains motorcycle route. It may not have the same name recognition as US 129, but it absolutely earns respect.

If your favorite rides combine history with twisty pavement, this one is hard to beat. Brushy Mountain gave the day a destination with some real atmosphere, and the Devils Triangle supplied the road character to make the miles between stops just as memorable as the stop itself.