Frisco Highline Trail – Springfield, Missouri
I parked at the northwest trailhead in Springfield, Missouri, ready for a morning ride on the Frisco Highline Trail—a route that carries both history and heart. The 35-mile trail stretches from Springfield to Bolivar, following the old Frisco Railroad line that once linked rural communities with larger markets. After the rail service ended in the late 1990s, local groups and the Ozark Greenways organization stepped in to preserve the corridor, transforming it into the second-longest rail-trail in Missouri (just behind the Katy Trail). Today, it connects neighborhoods, farmlands, and small towns, offering a peaceful slice of the Ozarks for cyclists, runners, and walkers alike.
The first eight miles out of Springfield were beautifully paved—smooth, fast, and quiet. Early morning light filtered through the trees, and the air had that early-fall crispness that makes you want to keep pedaling. After mile eight, the pavement gave way to a very firm crushed stone surface, still great riding but with just enough texture to keep you aware of the trail beneath your tires. The further I went, the more the surface changed—some sections were rutted and uneven, a reminder that this path has weathered many seasons.
The old railroad grade meant a gentle, almost imperceptible climb. I figured it would be a breeze coming back down. Around the 16-mile marker, I rolled into a larger trailhead parking area with a few cars and trucks. I had only planned on riding about twenty miles, so I was already past my turnaround point. I stopped for a fig bar, took a few gulps of water, and watched a young man climbing a tree while his girlfriend laughed and shook her head. As I passed, she smiled and said, “Good morning.” Simple, human moments like that stick with you on long rides.
Once I turned back toward Springfield, the truth of the ride hit me: the wind. A strong headwind made the return leg feel like an uphill grind, even on the downhill grade. It explained why my outbound pace had been faster than usual—I’d had the wind at my back without realizing it. Still, I didn’t mind. The wide-open landscape and soft autumn light were worth every extra push on the pedals.
The Frisco Highline Trail passes through a mix of forest, open farmland, and small creeks. Occasionally, the trees break open to reveal long, sweeping views of the Ozark countryside. In one stretch, locals had decorated the trail for Halloween—skeletons hanging from branches, ghosts twisting in the breeze, and a big hand-painted sign that read “Sleepy Hollow.” A few of the decorations had blown down, giving the scene an unintentional spookiness that made me smile.
Unlike some trails that pass directly through towns, this one mostly skirts the edges of rural communities. A few side roads branch off toward places like Walnut Grove and Willard, but most crossings were quiet. Only one had any real traffic; I waited for a pickup to pass and was about to cross when a motorcycle came from the right. We both stopped, nodded, and he waved me across. Small courtesies like that are part of what makes trail riding feel communal, even among strangers.
I saw plenty of other riders and walkers out enjoying the day—people soaking in the last warm weekends before winter. At one point, a skateboarder hopped onto the trail ahead of me. I was cruising along at about 12–14 miles per hour and couldn’t catch him. Eventually I realized his longboard was electric, humming quietly along the crushed stone. I finally passed him about a half mile before the end of the trail, both of us grinning.
Back at the Springfield trailhead, I spotted a couple working at the bike maintenance station. I asked if they needed tools, and the man said he’d just bought a used bike with a stubborn derailleur that wouldn’t shift right. We ended up chatting for nearly forty-five minutes. They were empty nesters whose youngest had just graduated from high school, now dreaming about life after kids—road trips, exploring, maybe even van life. I mentioned my setup, and offered to show them. I gave them a quick tour of the van. They were fascinated by how everything fit together: the bed, the power system, the compact kitchen.
It was a perfect ending to the day—two paths crossing at just the right moment. What started as a simple 20-mile ride turned into a mix of history, wind, laughter, and connection.
The Frisco Highline Trail may not have the fame of the Katy Trail, but it shares the same spirit: preserving the past while opening the way for new adventures. Each stretch of gravel carries echoes of old locomotives and the people who depended on them—and now, those tracks carry a different kind of traveler, one powered by legs, curiosity, and the open air of the Missouri countryside.