Slay The Dragon

Buffalo first forged the trail that later became a familiar route used by the Cherokees for centuries. It was so treacherous that it became an effective means of escaping the Trail of Tears. What is now US Hwy 129 boasts a rich history with as many twists and turns as the road itself. The scenic drive from the plateau, whether from Highlands or Cashiers, is well worth the two-hour journey, making it a perfect day excursion with some wild and crazy driving as the capper.

The infamous Tail of the Dragon is an 11-mile stretch of two-lane mountain road featuring 318 twists and curves, with nary a crossroad. It is the boundary between the Great Smoky Mountains National Park and the Cherokee National Forest, with its southern starting point at the intersection of Hwy 28 and US Hwy 129 near Robbinsville, NC. It is a mecca for bikes and sports cars, not only as a rite-of-passage but also for its mind-numbing beauty. Most would agree that the views alone, along this border between two spectacular and protected tracts of land, would be enough.

For Darryl Cannon, it was a life-changing place to start a business, taking him from a middle-Tennessee warehouse job to owning a lucrative and popular roadside attraction. He began coming up to The Dragon more than 20 years ago for a weekend getaway. Ron and Nancy Johnson were already there with their retail outlet, Tail of the Dragon, where riders could commune and grab snacks, souvenirs and necessities.

Darryl became a regular visitor, often snapping photos of riders from the side of the road. Many were his friends, and he freely shared their shots when asked. Eventually, an idea percolated, and the Johnsons fully supported it to enhance their customers’ experience. Killboy was a handle Darryl had used as a gamer. It became the name of his photography business, and when he wasn’t working in the warehouse, he was at The Dragon, taking pictures of every car or motorcycle that passed. The sign beside him advertised his website, Killboy.com, where anyone could search for an action shot of themselves and easily purchase it online. It was genius.

Before long, Darryl’s photography business became lucrative enough to take a leap of faith. He quit his day job and relocated near his entrepreneurial start-up full-time. A couple of decades later, he employs a team of photographers skilled at getting shots that sell like hotcakes to the thousands of riders and drivers who challenge their skills on the iconic stretch. There is an incredible inventory of t-shirts, custom signs, pins, patches and refrigerator magnets for sale at Tail of the Dragon, at the southern entrance. But, for many, a high-speed action photo of themselves is the ultimate take-away.

Like all successful entrepreneurs, Darryl has embraced ever-changing technologies for online photography and commerce. With his team, he continuously introduces improvements to the Killboy.com website for sorting and searching vast archives of photos so that customers can quickly find new images and access older photos. His success with Killboy.com and Tail of the Dragon has also freed him up to explore new ways to expand his footprint in the digital photography world. He has become a sought-after drone photographer, though he explained that it would never be appropriate for use on The Dragon for safety reasons. He is also well-versed about AI and how it can streamline his online commerce.

Southern Appalachia has a history of savvy locals capitalizing on the region’s natural resources. Roadside attractions, mom-and-pop motels and souvenir shops have long been reliable sources of income for generations of families. But Darryl Cannon is perhaps one of the most successful using a minimum of his resources. His attraction is well entrenched and famous, even internationally. Although his efforts in the digital space are remarkable and have promoted the area as effectively as any Madison Avenue agency, his smartest move was recognizing a built-in customer base at one of the country’s most beautiful road trips.

He also has an innate sense of gratitude for what he has been able to build and advocates for common courtesy, generosity and respect for the folks who live and work in the area or are traveling through, oblivious of the iconic drive they may have stumbled upon. “Sometimes, all it takes is one rude or aggressive driver. Someone gets harassed, and they may never forget or forgive.”

Darryl is also aware of his responsibility to everyone traveling The Dragon, not just his clients. U.S. Highway 129 is not the best route for large trucks, 18-wheelers and trailers longer than 30 feet are prohibited to prevent jack-knifes that can close the road down for hours. However, it was the only option following Hurricane Helene for a time due to closures on I-40. It became necessary to pause and work through the disruption, and he was quick to flag down trucks he knew could not navigate the sharp curves. He does not own the road, but he embraces his role as a helper to all and protector of the space. Everyone who runs the show, from the Motorcycle Resort to the photographers along the ride, is friendly and eager to make everyone feel welcome. The businesses collaborate seamlessly.

When you’re ready to slay The Dragon, taking time to learn before you go is recommended. Killboy.com shares daily highlights with their favorite photos, a selection of fantastic scenic photos, and even cabins for rent nearby. TailOftheDragon.com has a terrific write-up about the region's long history, maps, alternative touring routes, lodging, dining and events.