Reflections on Challenge & Community After Running Another 100-mile Race

In November 2024, I ran my third 100-mile trail race. It was my slowest and hardest. It hurt a lot — and I still loved it.

It’s nearly a year past the race as I write this — so why now? 2025 was a great year – backpacking, trail running, and a personal best in a road marathon– but I also feel that I missed the unique challenge a 100-mile race provides: a controlled edge-of-destruction feeling as you push yourself to your limits.

By tackling distances like this, I am actively choosing to see just how tough I am. Choosing to do hard things is why I love coming to work at Darn Tough – a brand that always chooses toughness and a challenge, because it means a better product and a more rewarding experience for the employees, our customers, and our community. High risk, high reward.

100 miles is a long way — especially mentally. At some point in a race that long, you will likely doubt your ability to finish. You’ll doubt your grit and toughness. And that’s why I love it. By allowing yourself to reach these low places, you can choose to overcome them and prove that you are capable of more than you thought.

If you quit, you might be keeping yourself from doing something epic.

I had no interest in running the 100-mile distance 5 or 6 years ago. Yet here I am with three successful efforts under my belt. Like the races themselves, it’s been a journey.

My hobby has humble beginnings. I was intimidated to run my first half-marathon in 2019, which at 13.1 miles is about 86.9 miles short of 100. The process was the same though; train, trust you can do it, and go for it. The body follows the mind.

I picked up running not long before that half-marathon, following my Appalachian Trail thru-hike. After walking all day, every day, I was antsy for movement. Running was the easiest activity to pair with everyday life at the Darn Tough Mill; I could do it anywhere, and it kept me active and in tune with my body.

Soon after this half-marathon, I was out for a long run with my best friend Ben. We were planning to run 18-20 miles, longer than anything I’d ever run. As we chatted over those slow miles, Ben said something I’ll never forget, “It’s fun to just keep going when it feels right. If you stop, you might be keeping yourself from doing something epic.”

The run naturally turned into 26.2 miles, my first time running the marathon distance.

Pacing Ben in his first 100-miler and Long Trail FKT

Fast forward to May 2021. Ben was training for his successful Long Trail Fastest Known Time (FKT) attempt. As a final training effort 6-7 weeks before the fateful FKT, Ben ran the 100-miler option at the Infinitus Race series, an event that offering races from 9 miles to 888 km (551 miles - yes, people do it).

I showed up to pace Ben for miles 34-54 of his effort and was enamored with the event and the people. All races run on the same 27-mile figure-8 course; longer races just do more figure 8s (or infinity symbols, hence the Infinitus name). Staggered starts with the same cutoff meant Ben ran alongside not only other 100-milers, but 250-milers and 888km attempters who had started days before him.

I quickly saw that the event is about creating a safe, supportive environment where people can push themselves to new feats. I felt smitten with this spirit of community-supported competition.

Trusting the Process: Training slow for a fast first 50-miler

With the love I felt while pacing at the Infinitus, I returned in 2022 to run my own race - the 88 km (54 miles – the Infinitus series loves 8s if you couldn’t tell). I worked with a coach on a training plan. Coach Joe McConaughy (The famous Stringbean if you follow Ultra-Running and Trail Records) had some good advice – trust the plan and the process. Run mostly slow miles, but make your workouts and long runs count.

The longest effort in my training plan was 50 km (31 miles), nearly 6 weeks before my 50-miler. This made me nervous. If I only ran 31 miles during training, where would those last 20+ miles come from on race day? And why so long before the race?

While individual long runs are important, the overall increase in mileage week over week matters more. 31 miles in one go takes a big toll on the body, so you want to do that early enough to recover. Don’t push too hard or too far close to the race.

Despite my anxieties, it all came together. The 50 miles were hard, but surprisingly easier than my 31-mile day 6 weeks prior. My body held up, and I ran faster than my goal time despite some unfortunate Memorial Day humidity-induced chafing.

Running my first 100-mile race

A year later, I was back at Infinitus for my first 100-miler. In the past 12 months I’d run my first sub-3-hour marathons (twice). Fast road races are rewarding but less satisfying than trail ultras – where pacing and self-care are essential. I was back for a bigger serving.

The 50-miler had taught me restraint. I expected the 100 to take me 24-30 hours or more; my primary goal was to finish regardless of how long it took. Pacing and nutrition would be key. I wasn’t just filling the tank; I was building it for the rest of the race.

100 miles demands self-care. In shorter races, I was able to just power through small issues – hot spots, chafing, indigestion, wet feet, muscle cramps. In a hundred, small issues can become race-ending if ignored. Taking a few minutes early to address issues can save hours (or the whole race) later.

Pacing matters: walk or slow down when you need to. Save energy for the long haul.

Taking on the night – accepting and overcoming my biggest mental hurdle

With a race this long, I dreaded the inevitable night. Many 100-miler runners quit after dark: you are tired, your pace slows down as you navigate rocks and roots, and you will be at it by headlamp for a long time. Morale can fade with the light.

My first 54 miles mirrored the previous year’s 88 km. As light faded, my pacer Ben (returning the favor from 2 years earlier) helped me refill running vest with snacks, water, a warm layer, and extra AAA headlamp batteries to send me on my next lap.

I set off into uncharted territory. Every step was the longest I’d traveled in a single effort. I was alone, and it was dark. Traveling in the nocturnal woods is not my favorite; I get spooked easily by sounds and silhouettes. It took a while to mentally find a groove, yet I kept moving, funneling my fears into slow forward momentum.

Finally, around mile 60, I relaxed into this new chapter and found an inner peace. A silent assurance. A super awareness of myself in its rawest form. By taking this leap into the unknown, I had found a new place for myself. Despite my fatigue, a new alertness emerged.

When you’re beyond tired, your brain resurfaces anxieties. I had a long night to think about concerns, both past and present, and past chapters that still needed closure. Running alone in the dark allowed me to physically move through them, processing my thoughts with a new perspective. Finishing this race wouldn’t make these problems go away, but it would prove that I have what it takes to take them on.

A friend had once told me that you will know yourself better than you ever have 60-80 miles into 100-mile (or longer) race. As promised, with life stripped down to the essentials, the night held up a mirror to my life, and I looked inside.

This long, thoughtful night is now a blur in my memory. What I remember most was the rejuvenation I felt as morning approached. As the pre-dawn birds began to chirp, I no longer needed my headlamp. The new day brought bravery and energy. My last 10 miles to the finish line were faster than any others I had run during the race.

Finishing the Race: The journey is the destination

Those last 10 miles were amazing. Daylight and fresh runners lifted me; 25-hour aches faded and my pace quickened towards the finish.

Honestly, crossing the finish felt a little anticlimactic - friends congratulated me as the race director handed me a Belt Buckle (a 100-miler tradition).

Proud as I was, what I felt during the race was more fulfilling. I discovered something way better than the accomplishment itself in making it happen. As I ate a huge post-race meal later that night, I told my wife Anna that this wouldn’t be my last 100-miler.

Back for more in '24

The rest of 2023 brought a lot of excitement – my wife Anna and I thru-hiked the Continental Divide Trail southbound - an amazing experience for a different blog post. Walking all day, every day, for 5 months builds an amazing aerobic base, especially for slower, longer efforts like ultra-marathons.

Coming home in November was a struggle; as with my Appalachian Trail hike 6 years prior, I was antsy for movement. But unlike that previous post-hike energy-burning desire, we were headed into winter.

Build to Riverlands

Winter training is hard — think dark, ice, snow, rain, and whatever else Vermont wants to throw at you. It’s challenging to scrape up any motivation. I signed up for a spring race to help get me out the door on those nastier days. The race was the Riverlands 100 miler, Maine’s oldest (and only!) 100-mile race. It was exactly like what I wanted – rugged, remote, and run by a small, close-knit community.

Two close friends, Rob and Lance, agreed to come along to support and pace me. Both Lance and Rob have ten+ 100-mile race belt buckles, so I knew I’d be in good hands.

A bit about Lance and Rob (and about crewing)

These two fellas are the best. On the drive to Maine, we laughed, played obscene music, and joked around. Later at the campsite, I cried from laughing at a stupid dice game. The boys helped me stay calm before the race and remember that, in the end, it’s all about connecting with yourself and others.

It’s a LOT to ask friends to crew you for a big event like this – not only are they giving up a precious weekend for your goal, but it can be a lot of hurry-up and wait. But I could not have been in kinder, more experienced hands.

Before bed, we talked race tactics. The race was four laps of a 25-mile course – a mix of single track and ATV trails through the beautiful Androscoggin Riverlands State Park. The race allowed pacers any time after mile 50 - the last two laps. Lance would take the 3rd lap, then Rob would bring me home during the final 25.

Race Day – Riverlands 100

We woke early for the 6 AM start. Not surprisingly, I hadn’t slept well. We packed up and drove to the start line, headlamps bobbing in the frosty air.

At the start I spotted Brian, a runner we’d met the night before, and we fell into stride once the race began. Brian and I cruised the first lap, talking easily for 5 hours. Miles go faster with a friend. The weather was lovely, and spirits were high. I logged mental notes about terrain and the aid stations; important intel for the 3 laps to come.

Brian and I finished the first lap together, then split to our respective crews. Rob and Lance were eagerly awaiting me with a hot quesadilla and fresh shoes and socks. The best feeling. For longer trail efforts like this, I choose run or hike Lightweight with Cushion styles – the perfect mix of lightweight breathability and cushioned comfort.

The second loop proved the hardest. I was alone and hit a wall at Mile 35. Doubt crept in: “If I feel like this already, will I survive 65 more miles?” I slowed down a hair and focused on nutrition. Eventually I worked through it. By mile 45, I had the halfway point in my sights and finished the second loop as dusk set in.

After the hard second loop, I took 15 minutes for self-care – new socks, shoes, and more real food. Then I was off into the night with Lance, my third-lap pacer. His supportive energy spurred me on – exactly what I needed. An ultramarathon veteran (and one of the few 888 km finishers at Infinitus), he knew exactly how to keep me steady. I don’t remember many details from that lap, but we had a good time, maintaining levity through jokes and conversation.

The same can be said for Lap 4, when Rob accompanied me for the final stretch. Strong, thoughtful, and good humored, he kept me moving and made sure I got what I needed at aid stations without cooling down or losing time. By miles 80-90, I was fading, but Rob was there to help. The final 5 miles of the event, like at Infinitus a year before, were my fastest.

At the award ceremony, the race directors noted that every time I finished a lap, I was smiling, as if I was actually enjoying myself. Accepting my belt buckle, I assured them I really had. It wasn’t easy, and I was proud of that.

Riverlands was a different beast than Infinitus a year prior. I had a stronger aerobic base from my CDT hike, more support from veteran ultrarunners, and company through the lonely darkness. It was still difficult, but the mental hurdle came earlier in the race.

Like after my first 100, I knew I’d be back for more. Another 100-miler was already calling.

Rough build to RUTFest

Following Riverlands, I set the goal to run another 100 miles later in 2024, in November at RUTFest - the Richmond Ultra Trail Festival. RUTFest is a 36-hour community running event by the Richmond Trail Running club at the Catamount Center in Williston, VT. It’s less of a race than a celebration of personal challenge and time outside with friends.

The figure-8 course includes two loops totaling 7 miles – a wooded 4-mile loop, and a mostly-open 3-mile loop. At the center of the figure 8 sits an aid station with hot food and fun. The race is communally-run: athletes cook, bring food, and volunteer. Entry fees are by suggested donation, and all raised funds go to the Catamount Center and other local non-profits. All community, all heart.

Runners can start anytime between 6 AM Saturday and 6 PM Sunday, going as far or as short as they want. Some folks run just a lap or two, while others go beyond 100 (Course record sits at 133 miles currently). RUTFest captures what running is all about: pushing yourself and supporting one another.

Training was going well, until I got sick in August… then again in early September… then (you won’t believe this!) sick a third time with Lyme Disease in late September. I logged some long runs, but recovery was slow and inconsistent. My 100-mile goal was in jeopardy. Still, the event’s low-pressure vibe was encouraging. If I didn’t hit 100 miles, I’d still have fun and see friends. I planned to toe the line, be optimistic, and relax into it. The body follows the mind.

Race weekend was cold but warmed with sun. Tasty, hot food at the aid station and warm community kept morale high. You could always find a friend to run the next loop with you.

The distance ticked by, but I felt the miles were more physically grating than my last two 100s. I was sore; sickness had taken away a lot of my fitness. Mentally though, I felt good.

As I hit 100-km / 62 miles, the nighttime temperatures plunged into the 20s (early Vermont November, remember) and I hit a wall. So I crashed for a 3-hour nap in my car. Still sore, but more mentally clear and morally invigorated, I got back out there to greet the sunrise over the frozen grass and take in the striking views of frosted Mount Mansfield and Camels Hump.

By mile 75, my ankles screamed, but nothing felt dangerous. I grabbed my trekking poles and decided to hike most of what remained. The last 25 miles were hard, but I never doubted that with the support of my friends and a little grit that I could do it.

I came in on my final lap and proudly accepted my belt buckle and hugs from my friends. This one meant a lot and was even more special than the prior two. It meant more to finish because it was harder and I had an entire community of like-minded people supporting me.

What's next?

Running the 100-mile distance has taught me that progress isn’t about going faster or harder. It’s about patience, trust in yourself, community, and challenge. From battling doubt during training and races, and finding joy and support from my community, every race has reminded me that endurance is as much mental as it is physical. True toughness is about showing up for yourself and others and trying your hardest – not just when things get hard, but because you know they will.

To run 100 miles is to know yourself better than you ever have. The belt buckles are nice, but what keeps me coming back are the insights into myself and moments of clarity along the way that doing something tough provides.

Whether it’s your first 5k or your fourth 100-miler, every step forward is a chance to grow, test your limits, and discover that you really are capable of more than you think. The body follows the mind.

About the Author

Owen (Sir Owen VanGrizzle on the trail) works in Product Design and Development at Darn Tough. He's a resident sock tester, having thru hiked the Appalachian Trail in 2017 and Vermont’s own Long Trail twice. Owen and his wife Anna completed the Continental Divide Trail in 2023. Off the trail, Owen serves on the Board of Directors for the Green Mountain Club, with the mission of making the outdoors of Vermont accessible to everyone.