Jenny’s Creek Bike Ride

I woke at the Harvest Host farm near Salyersville, Kentucky, to a thick blanket of fog draped over the fields. The temperature hovered in the low forties—the kind of morning that makes coffee taste better and everything outside look a little mysterious. I made a quick breakfast of blueberry pancakes and packed up for the day’s ride on the Dawkins Line Rail Trail. The plan was to start from the Jenny’s Creek Trailhead, about an hour’s drive from where I was staying.

As I neared Salyersville, I decided to look for coffee, but the town was still quiet. The only open options were back toward Paintsville, where most of the local businesses seemed to be clustered. I turned around and drove a few miles back. The Coffee House looked promising—a small, independent café tucked into a row of storefronts. I ordered a latte, settled at a corner table, and spent a few minutes processing photos from the day before while the fog slowly began to lift. Once the caffeine kicked in, I packed up and headed toward the trail.

AllTrails led me to what was supposedly the Jenny’s Creek Trailhead—but there was no parking. Google Maps wasn’t any better. I looped around a few narrow roads until I finally spotted a small wooden sign pointing toward the actual trailhead. The detour was worth it. The Dawkins Line Rail Trail runs for thirty-six miles through eastern Kentucky, following the old Dawkins Branch of the Chesapeake and Ohio Railway, which once hauled timber and coal through the hills of Johnson, Magoffin, and Breathitt Counties. After the line was abandoned, Kentucky State Parks turned it into a multi-use trail—the longest rail-trail in the state. It’s a smooth, scenic ride, with eleven trestles and the 662-foot Gun Creek Tunnel, winding through forests, pastures, and small Appalachian communities.

The parking area sits about a mile from the trail’s start and includes pit toilets, a corral for horses, and a set of concrete steps for mounting. I couldn’t quite figure out why the steps were there—maybe they’re used to help kids or beginners mount up—but it added to the charm of a trail that clearly serves everyone from cyclists to horseback riders.

The first few miles were flat and easy, winding past clusters of small homes—some new, some clearly more than a century old. A few were abandoned and leaning into the weeds, while others showed signs of care: fresh paint, laundry on the line, smoke rising from a stovepipe. There were a few tiny community centers, trail parks, and even a farm preparing for a pumpkin patch event. Beyond that, the trail began its steady ten-mile climb toward the tunnel.

This time of year, the trees were just starting to turn, the hills glowing with orange, red, and yellow leaves. The air stayed cool in the shade, but when the sun broke through, I warmed up quickly. Fallen leaves covered the trail in patches, hiding the occasional walnut or stick that could make for a surprise if I wasn’t paying attention. At one point, the path ran straight through a farm with barns on both sides, and a dog sat squarely in the middle of the trail. I checked AllTrails to make sure I hadn’t wandered off route—nope, this was still the right way. As I rode closer, I picked up speed, half-expecting him to charge. Instead, he stood, stretched, and quietly stepped aside before lying back down in the grass.

I continued another fourteen miles north, through the Gun Creek Tunnel and a few more quiet stretches of forest before deciding to turn back. I didn’t want to drop too far down the other side, knowing what the climb would be like on the return. The ride back was mostly downhill—smooth, fast, and just technical enough to keep me alert.

The damp leaves, scattered walnuts, and low afternoon light made for a few tricky moments, but it was all part of the fun. By the time I reached the trailhead again, the fog had lifted completely, the air crisp and still. It was one of those rides that stays with you—a perfect mix of challenge, history, and the quiet beauty of Kentucky’s backroads.

I noticed a plaque near the Jenny’s Creek trailhead parking area. The small plaque described a Civil War skirmish that took place on this quiet stretch of land. Later, I read more about it online. In January 1862, Union and Confederate forces met here in what became known as the Battle of Jenny’s Creek—a short but intense fight over control of the mountain passes and the coal routes that supplied nearby towns. The Union troops eventually forced the Confederates to retreat, but not before both sides suffered losses in the frozen hills. Standing there, it was hard to imagine gunfire echoing through this peaceful valley now lined with maples and farms. It’s an easy place to pass by without knowing the history beneath it, and I found myself wondering how many locals even realize a battle was fought right here.

When I got back, I took a break, made dinner, and did a quick cleanup inside the van. I was parked in a large, empty lot, and no one else ever pulled in. For a while, I thought about just staying there for the night—it was quiet, flat, and easy—but decided to move on. I headed toward Charleston, WV.

I drifted off later, thinking about the peaceful ride up the mountain. I’d had the entire trail to myself.