I have been hiking the Sheltowee Trace Trail in Kentucky over the past 8 years. The 300 mile trail from Morehead, KY to Rugby, TN goes through the heart of beautiful rolling woods- hugging Cave Run Lake, meandering through the epoch Red River Gorge, and then tightly winding around the perimeter of Laurel Lake. After hiking across the dam at Laurel Lake, the Sheltowee follows the Laurel River 2 miles where the trickle of a tributary empties into the majestic Cumberland River. From there, the trail heads south to Cumberland Falls, the premiere tourist destination of southeastern Kentucky. The trail goes west to the South Fork of the Cumberland River and then south until it reaches its final destination in northeastern Tennessee. 

Three hundred miles is a long way and so I hike it in increments. I have led 8 unique trips with 17 friends and family members since starting the hike in November 2016. I am most proud of going with my son, Isaac, on three of those journeys. He has joined me for 57 of the 191 miles that I have completed thus far.

It was in the Big South Fork National River and Recreation Area of the trail where I found myself in May 2024 with my friends Slater, Jason, and Clyde. We were prepared for the most ambitious hike that I have ever planned – 43 miles over 4 days. As we neared our drop off point, we saw a black bear scrambling into the forest as our van rambled along the gravel road that terminated at our trailhead, Peter’s Mountain. None of us had seen a bear before in the wild. It was relatively small, but I am sure bigger than my 200 lbs frame. We were thankful that it was about five miles from our starting point AND we would be walking in the opposite direction. Clyde dropped us off and we confirmed our plan to meet up at Yamacraw Bridge – 42 hours and 29 miles later.

Three miles into the Sheltowee, we encountered another black bear, about the same size as the first, that ran uphill and behind a large boulder as we unsheathed a hatchet and prepared for the worst. We neither saw nor heard any more of the bear after we passed the bend where it emerged. Quickly, we descended to Desperation Creek and on towards the Cumberland River. 

The wildness represented in an animal like a bear is distinctly different from the wildness of a unique ecosystem, far from civilization. A beautiful, remote landscape elicits the joy of being the audience of a rare spectacle, while an animal strikes the fear of being part of the spectacle, where actions have real consequences in a unique and unpredictable situation. Wilderness is the setting where our historic relationship to nature can be experienced. In a controlled environment, a zoo for example, the wildness of a bear is obscured by the domestic surroundings. With the trappings of safety, it is impossible to truly feel the nature of the animal. Hiking brings you into the liminal space of wildness and unforeseen scenarios.

We all stepped to that threshold before the bear – and the feeling it elicited – passed and was not seen again.

At sunset, we found a beautiful beach camp location along the Cumberland. We woke to rain. And it rained, with a few hours of reprieve, for the next 24 hours. We were prepared for the weather, but it was nonetheless painstaking. When attempting to hike 18 miles in a day, there are many decisions to be made around conserving energy, pushing through pain, finding ideal rest sites, and understanding the needs of fellow travelers. Even very practical decisions like following a map are not always straightforward. 

The rain abated early on day three, but within 2 miles, we had to cross a creek carrying the previous day’s rain – waist deep. Despite the challenge, we made it to our rendezvous point at Yamacraw Bridge on time with Slater departing and Clyde joining us for the remaining 14 miles of the trip. We had hopes of potentially, with good weather, finishing the trail a day early and heading back home to appreciate the luxury of dry clothes.

Good fortune eluded us as we hiked into the Yamacraw Trail Race, a 40 mile out-and-back trail run competition. On a muddy trail. What you might call a quagmire. In hopes that we would not be following the racers, I made a wrong turn that led us almost a mile off trail. When we returned to the Sheltowee, the three of us, each with heavy packs on, were intermittently being yelled at “Runner behind” or – spotting a runner in front – we would shuffle into the mud at the edge of the trail. I had never experienced anything like this traffic. The trail conditions, physical tiredness, and general chaos of sharing the trail confounded us.

Mud slicks and loose rocks
Rambunctious runners on trail
We’re slow and steady  

We lost sight of the river and walked into the hills, again mistakenly off trail, but luckily hiking more or less parallel to the Sheltowee and without the disturbance of runners. However, as we veered back towards the main trail 4 miles later, we discovered on the map a spaghetti section of overlapping trails in the area of Yahoo Arch and Yahoo Falls. We were close to the largest campground in the area and there were many trails between us and the Cumberland River. We merged into this poorly marked trail system at Yahoo Arch. 

This part of Kentucky is known for its monumental rock formations. The epicenter, about two hours northeast of us, is named “Natural Bridge State Park” for the extraordinary sandstone arches emerging from the forest. Only the iconic Arches National Park in Utah contain a higher density of these geological marvels. 

Yahoo Arch, in my estimation, is the most impressive arch that I have seen in Kentucky. There are multiple levels, caves, and a spiral path that conjured the impression that we were in a sort of M.C. Escher.prehistoric rock sanctuary – impossible to capture on camera or video. It was our first pause for true enjoyment since falling asleep along the river two nights before. A kind of stare up towards the heavens and slowly rotate in place kind of pause. Being here was not part of the plan, but the gravitas of this place would ultimately help us find our way out. 

Reluctantly, we continued- not 100% sure how to link back to the Sheltowee. We saw our first  non-runner on the trail in over 24 hours. A guy from Charlestown, IN with a curious Caribbean accent. Being tired, I took a bit of a break to talk to him while Jason and Clyde walked on. The conversation sparked when he mentioned that he was dabbling in semi-professional photography. Before going our separate ways, I formally introduced myself and he gave me his name- Mike.

When I caught up to Clyde and Jason, it began raining again. The best we knew to do was to walk north and hopefully the spaghetti would straighten out. We headed down towards the creek that would eventually lead to the Cumberland. Crossing the water, Jason fell. Clyde unbuckled the pack from his waist and Jason staggered to the creek edge. He laid there. We were lost. Darkness was approaching. We were still 6 miles from our final destination.

While not spoken, I felt our motivation to complete 43 miles was broken.

We crossed another creek and then I scouted for a trail by climbing a steep hill to what was hopefully the Sheltowee. This was not the way.

Wet toes, muddy boots 
Gingerly placing trek poles
Feet throb, descending  

We hiked back to where Jason fell and then south in the direction of the campground. We heard noise nearby and hoped we were close. Once we turned a corner on the spaghetti trail, we realized that we were at Yahoo Falls. 

The waterfall was majestic. While not wide like Cumberland Falls, it more than makes up for it in height. And the previous day’s rain flowed from above. The noise we heard were boys playing at the base of the falls. Unfortunately, this also meant that we were still not imminently close to the campground. 

The rock shelter behind Yahoo Falls contained a wide arcing trail. Far on the other side, I saw a man taking photographs. It looked like it might be Mike. 

I yelled, “Mike, is that you?” 

“Yes,” he responded. 

“Good to see you again. May we talk?” 

“Of course,” he affirmed.

I quickly walked over, wincing at the pain in my feet. Jason was stationary and Clyde assessed other pathways.

I laughed with Mike for a moment, not sure how he had photographed Yahoo Arch and returned to this spot, ahead of us. Gazing upward, he told me it was the highest waterfall in Kentucky. He had planned to go straight back to his car, but felt inclined to photograph these falls one last time. 

I told Mike what had transpired over the last hour. In a moment of full transparency, I acknowledged the awkwardness of what I was about to say and then did my best to tactfully state that, ideally, we would like to get back to our car- ASAP. I asked  if he would be willing to drive the three of us and our backpacks the 15 minute drive from Yahoo Falls campground back to the church where our van was parked. Without hesitation, he said yes. I yelled across those beautiful falls for Clyde and Jason.

We followed Mike to his car, giving him time to take more photos as he guided us on the trail. Clyde asked him how to view his photography and he told us to check out Mike Heaven on Facebook. We had to clarify that his last name is Heaven. Indeed it is, he assured us. Jason may have made a remark about him being an angel. 

On the fifteen minute car ride, we learned more about Mike. He is from Brooklyn and the youngest of 9 brothers. He moved to Louisville to go to college. After graduating, he became an accountant and began doing travel photography. With humility, Mike mentioned how surprised he was to gain an online following of 25,000 people in less than a year. 

When we returned to our van at Flat Rock Missionary Baptist Church, Mike reluctantly took the money that I offered him for his nearly miraculous assistance. Before getting back into his car, he walked over to a long, intact snake skeleton in the church parking lot to take one final photo before being on his way. 

Across the wide arc
I call to photographer
Yahoo Falls angel