Where the Road
Meets the Trail

Words by Lou Serafini
Photography by Ansel Dickey, Joe Viger and Tom Dils

What’s not a road race, not a cross country race, not a trail race? The Vermont Overland TRAIL is a unique event that marries three different formats: trail, cross country, and road. Developed from the Vermont Overland bike race, one of the biggest and oldest gravel cycling events in North America, this might be the only running race of its kind. It begs the question: if the best road and trail runners met on course, who would come out on top?

Vermont is home to some of the most unique and rugged terrain in the US, boasting over 8,000 miles of unpaved road. Vermonters love their dirt roads and scenic highways and to a runner, it’s basically paradise. Endless soft surfaces, carless stretches, and unlimited places to explore. These elements add up to make it the perfect place to experiment with different racing formats.

This is not the first race featuring Vermont’s dirt roads. The Covered Bridges Half Marathon in Pomfret, VT, sells out in minutes each year. They open registration in December, six months prior to the race, and once it’s sold out, that’s it, you’re not getting in. There’s no waitlist. In addition to the CBHF, Vermont features dozens of popular trail races like The Vermont 50 and The Catamount Ultra. Given the popularity of these other races and the dramatic growth within the gravel cycling world in the past decade, it’s easy to see the potential in this new unique racing format.

The inaugural Overland TRAIL took place on Memorial Day at Ascutney Resort in West Windsor, VT. Only two hours from Boston and 90 minutes from Burlington it’s easy to access and features one of the most robust trail networks in all the Northeast.

Many runners wore hydration packs for the 15.5 mile course which covered over 2200ft of climbing but I opted for a hand-held bottle with some Skratch. I wanted to have the option to refill at the aid stations while maintaining that light, racey sensation. Even though it was a balmy 75 degrees and humid at the start, much of the course was naturally shaded within the beautiful Vermont forest.

At the starting line, they announced some of the top competitors. They ranged from a National Champion Ultra Marathoner to a four-minute miler. I’ve never been in a field with that range of athletes and I had no idea what to expect. As an inexperienced trail runner and strong road runner, I knew my best bet would be to push on the roads.

The gun went off and within the first mile we ran on a dirt road, a singletrack trail, and a grassy hill that resembled an XC course. The first 5 miles were truly a learning experience for me as they were 95 percent trail. 

Here’s what I learned:

• The miles don’t really fly by on the trails. I’m used to miles just sort of melting away but on singletrack, everything takes longer. There are twists and turns, roots and rocks, and other elements that slow you down. I was challenged to get out of that racing mindset at times and just focus on staying upright and not rolling an ankle.
• Running downhill on trails is a skill. I made up a lot of ground on the uphills and eventually got comfortable enough to push on the flat sections but what I found was that no matter how much of a lead I had, I would be quickly caught and passed on downhills in the trails. It was crazy watching these experienced trail runners bound through rocks and roots while I gingerly shuffled down the descents.
• Trail etiquette is pretty great. If you want to pass someone on a narrow trails, you simply ask (people were asking me a lot on the downhills). It’s just a concept you’re not really expecting in a race format but as one of my competitors described after the race, if you’re going faster than someone and they refuse to move over, it’s obnoxious.

When we finally exited the woods around 10k, I was sitting in fourth place with places fifth to seventh on my heels. The top three were nowhere in sight but getting out on the roads was like taking the training wheels off a bike. I could finally open my stride and run comfortably. All alone for the next 5k, I enjoyed rolling dirt roads and gorgeous views, while focusing on maintaining a controlled rhythm.

I was met at the second aid station with pickles and untapped maple water. Not a combination you would think works, but in the moment, it did. Finally, I could see third place 150m up the road, but we were about to enter the trails again and my fun on the roads was about to be over.

After pulling even with third place, we excited the woods and were met with a cross country type of terrain. A grassy path that looked out on a sweeping mountain view. Running on uneven grass after ten hard miles wasn’t ideal but the views more than made up for it.

Onto the final dirt road push. I knew this was my last chance to make a move on the leaders so I pushed hard. Past landowners doing weekend yard work, under covered bridges and up and over long climbs that were always rewarded with a great view. Second place was still nowhere in sight. Just as I was getting content with settling for a podium finish, I saw Eric LiPuma headed into the woods for the final trail section and the race was on.

We were passing runners finishing the seven-mile race. Even though I was moving faster than him, we were back in the trails so I couldn’t shake him. I focused my energy on surging the uphills where I knew I had the advantage and trying to maintain contact on the downhills. This section transported me right back to high school cross country. The final stages of a race, both of us giving all we had, not knowing when we’d pop out of the woods and see the finish. We wound past waterfalls, hurdled fallen trees and passed over wooden bridges.

Finally, I was able to get a gap up the final climb and just as I exited the woods for the final half mile stretch, I saw the leader, Dan, coming back to me. This was a surprise. I didn’t think I was close. We entered another sweeping grass field where the course switchbacked down to the finish. As Dan navigated the uneven surfaces he caught a snag and went down. He popped right back up and just as I passed him to take the lead for the first time of the day, 15.5 miles and 1hr, 49 minutes into the race, he surged right back past me and into the finish, crossing the line in first place where he was met with champagne showers.

Who’d have thought two hours earlier that such a long, demanding race, with such a cast of characters would come down to a sprint? It was as if we were finishing an all-out mile on the track. I grabbed an IPA, another thing Vermont has no shortage of, and cheered on all 200 competitors that followed us. 

The after-party confirmed my theory that this is indeed a friendly and wholesome community. I met all different types of runners from across New England who had come out to experience the one-of-a-kind course. Even the runners who had tough days in the heat had smiles painted on their faces. That was the beauty – none of us were racing the clock. Actually, I’m not sure I checked my pace once… We were all just out there racing hard and having fun. 

My friend and I completed the day with a soak in the river behind Butcher and Pantry, one of the local race sponsors. We told tall tales of our race experiences, excited to give it another go next year. Based on the success and drive of the race organizers, I’m confident this event will continue to grow for years to come. Hopefully more runners will begin to step outside their comfort zones to a world where the road meets the trail.

For more info on this race, check out their website here.