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The Long Trail traverses the scenic, but challenging, Green Mountains of Vermont. (Jocelyn Smith Photo)

Lessons From The Long Trail

When a runner set an incredible FKT on Vermont’s Long Trail last summer, she did more than etch her name in the record books. She inspired those around her.

By Jocelyn Smith

It’s not every day you get to live alongside someone who attempts the unthinkable.

Morning after morning, I sat across from Chewy with coffee between us, listening to her talk through training goals that sounded like entire hikes in themselves; her “short days” were most people’s full efforts. She’d mention a twinge in her leg or mutter the doubt every ambitious person eventually faces: Who do I think I am?

Looking back now, those coffee sessions were the earliest rumblings of something bigger. We were two women, daring to believe we might stretch further than anyone expected, armed with caffeine, ridiculous optimism, and a lot of audacity.

The Long Trail, a 272-mile trail tracing the spine of Vermont, isn’t just the oldest wilderness footpath in America; it’s also among the most stubborn. It was built before trail design softened climbs with switchbacks, back when “up” simply meant straight up. People often wonder why the Long Trail feels brutal, and the answer is simple: it goes up the hard way and comes down harder; you can leave your knees at the terminus.

For those inclined to challenge that, here’s a comparison I never tire of repeating: the Long Trail’s roughly 66,000 feet of elevation gain is nearly equal to Oregon’s section of the Pacific Crest Trail, which is almost 200 miles longer. The passes out west may be dramatic, but in Vermont, elevation is earned through attrition, not aesthetics.

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Tori “Chewy” Constantine set the unsupported Fastest Known Time on Vermont’s Long Trail in August 2025. (Jocelyn Smith Photo)

Now take that terrain and compress it into five days, 19 hours, and 29 minutes. That is the current unsupported Fastest Known Time on the Long Trail, an average of over 50 miles a day with nearly 12,000 feet of climbing stacked into each one. Unsupported means unsupported: no town food, no accepting extra water or a battery pack, no pacers, no hugs. Just your body, your mind, your pack, and a dream most people would be afraid to admit out loud.

My friend Tori “Chewy” Constantine holds that record.

The evening before her attempt, on July 30, we arrived at the northern terminus. Her anxiety filled the car the way weather fronts move across ridgelines, but as we slung backpacks over our shoulders and made our way toward Journey’s End Camp, a smile finally surfaced. This was it. The point of no return.

We had the shelter to ourselves, which was perfect because we needed space for one last pack explosion, one more calorie check, and one final night with a real sleeping pad. Excitement kept us restless. Chewy had quietly put in an outrageous number of training hours while balancing her full-time job as a nurse. Meanwhile, I could barely convince myself to run that week. Her dedication was humbling.

We both woke before her alarm. Without speaking, we began packing. It was time.

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Tori “Chewy” Constantine earned her pizza with her record-breaking, multi-day effort. (Jocelyn Smith Photo)

We night-hiked to the border monument, adrenaline buzzing between us. Chewy looked electric, weather window perfect, body primed, spirit sharp. I don’t think anyone in her life doubted she could do this, but what struck me was that she believed it too. She glowed with the kind of energy only slightly unhinged people possess, and only somewhat unhinged people truly understand.

Then I watched her walk away, swallowed by darkness, and the weight of it hit me: she’s really doing this.

I stalked her Garmin dots like a hawk. I obsessed over her speed, where she stopped, how long she lingered. I waited for calls so I could hear how she sounded, reassure her, distract her. In unsupported FKTs, you can call people (at the cost of precious battery life), so her choice to call meant she wanted voices other than her own in her head. The tone of those calls shifted as the days went on: exhilaration gave way to exhaustion, and excitement turned into demands for maple creemees.

The last day was brutal. She called. Sixty miles to go. We reminded her that 60 was nothing compared to what she’d already done, but she wouldn’t hear it. Fatigue had hollowed her voice. She didn’t want to quit, but she desperately wanted to be done.

Friends hiked in from the southern terminus, and we waited in the rain with a handmade crown. Her phone had died, no more updates. Every branch crack made us spin around. Night fully arrived when a wild, mud-streaked Chewy finally emerged, hobbling but fierce. She collapsed, disoriented, before she processed what had happened. Then she smiled.

She had done it.

Five days, 19 hours, 29 minutes. The new unsupported Long Trail FKT.

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Tori “Chewy” Constantine at the southern terminus of the Long Trail after setting a new FKT in August 2025. (Jocelyn Smith Photo)

We hiked her out, drove home, and just like that, this wild thing she’d been chasing was over. And how do you return to normal after breaking something that big?

We slipped back into morning coffee sessions to debrief her effort. She was humble, almost bewildered. It seemed she hadn’t fully believed she did it, or perhaps she still hadn’t found the edge of her capacity. That’s who she is: a woman who keeps pushing, keeps searching, never afraid of hard things.

Watching her changed me.

I learned more from her attempt than she will ever realize. I was one of her point-people, fielding calls, cheering her through hallucinations, coaxing her through doubt. Now roles are shifting. As I prepare for Project Perseverance, a 10,000-mile year, she’ll be one of mine.

What gives us women the audacity?

It could be mornings like those, coffee in hand, fear on the table, ambition spoken aloud, because witnessing another person’s courage can ignite belief in our own. Chewy didn’t teach me that records are breakable; she showed me that limits are negotiable.

When I pass through Vermont on my own attempt, I know I’ll feel her shadow on those climbs. I’ll think of her hobbling toward the finish, blistered and delirious, still refusing to quit, reminding me that pushing boundaries requires courage and resilience. And when I’m tired, afraid, or questioning why I chose something this hard, I will summon the courage she proved was possible.

Sometimes, we don’t learn to start until we watch someone else finish.


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Jocelyn Smith is a Vermont-based long-distance hiker, writer, and digital creator known on the trail as Unhinged Hiker. She’s currently preparing for Project Perseverance, her 10,000-mile calendar-year trek across seven major U.S. trail systems in 2026. Her work focuses on storytelling, mental health advocacy, and expanding representation in the outdoor community. Follow her journey on Instagram at @unhingedhiker.