Riding the Vermont Overland 2024 edition was everything I’d hoped for and more—a real test of resilience, technical skills, and grit. But for me, this wasn’t just an event; it was a turning point, a culmination of eight months of training that started with me struggling to find my place back on the bike. Training for the Overland wasn’t just about fitness—it was about rediscovering a part of myself I thought I might have lost for good.
From the moment I signed up, I knew this event would be different. It wasn’t just about ticking a box or chasing a result. It was my way of marking a return, proving to myself that I still had the drive, the grit, and the resilience to take on something as daunting as this. And with 55 miles of relentless Class IV roads, over 7,000 feet of climbing, and more than a few moments of self-doubt, the Overland made sure I earned it.
The morning of the event started mercifully late with a 10:00 AM start, giving me time to take a deep breath and reflect. As I lined up a few rows back, I couldn’t help but feel the weight of the moment. It wasn’t just nerves—it was pride. Standing there felt like an achievement in itself after years of being away from big events like this.
The first miles were deceptive—smooth gravel climbs that almost lulled me into thinking this might not be as brutal as I’d feared. But the first Class IV section snapped me out of that dream quickly. Within moments, I was off the bike, scrambling over impossibly rocky terrain with riders jammed in front of me and behind me. I’d scoped out this section the day before and thought I could ride it solo—but in a pack, it was chaos. As I wrestled with my bike, I had to laugh to myself: You wanted a challenge, didn’t you?
From there, the event was a rollercoaster of highs and lows. The climbs were where I felt most like myself—where I could push, dig deep, and tap into the work I’d done throughout the year. But the descents? They were a humbling experience. As a roadie from New York City, my technical skills had never been tested like this. Riders I’d passed on the way up flew by me on the treacherous descents, and I found myself picking my way down, questioning if I’d ever find the confidence to let go and just trust the bike.
Rich Trail was a special moment, for me and for everyone else too I think. Halfway through the event, this infamous climb brought almost everyone to a crawl. I wasn’t ashamed to join the walking crowd—it was impossible not to—but when I reached the top, I paused for a moment, looking back at the trail below, and felt a wave of gratitude. Then someone looked at me and said ’This is not Central Park, is it?’ Central Park or not, I was here, pushing through, and no matter how hard it got, I was having the time of my life.
As the miles passed, I found myself reflecting on the parallels between the Overland and my journey this year. Both were about trusting the process, and proving to myself that I could show up and face the challenge again. There were moments of pure exhaustion but also flashes of joy—catching a stunning view at the top of a climb, finding camaraderie with other riders, or simply feeling my body respond to the training I’d put in.
Crossing the finish line wasn’t just about completing the event. It was about reclaiming a part of me that I’d been working all year to find again. Vermont Overland reminded me why I fell in love with the bike in the first place so many years ago—not just to satisfy my competitive side or fitness, but for the connection to something bigger: the land, the community, and the unrelenting pull to see how far you can go.
In 2025, I’ll come back with more preparation, better technical skills, and even more respect for those demanding Class IV roads.
- Gil