Finding a Sense of Home
on Vermont’s Gravel Roads

NELSON BROWN 〡 Sept 3rd, 2025

I grew up in Woodbury, Vermont, a small town stitched together by dirt roads, ponds, and community. After years away in the White Mountains of NH and Seward, Alaska, I came back to Vermont in 2020, first settling in Waterbury, then Montpelier, where the floods hit hard, and now in Waitsfield. Without planning it, this three-day bikepacking trip carried me through every one of those towns I’ve called home.

Labor Day weekend often means crowded highways and long drives. This year, I wanted none of that. My goal was simple: build a bikepacking loop starting and ending at my doorstep in Waitsfield, no cars, no shuttles, just pedaling. The result: 124 miles, more than 12,000 feet of climbing, and roughly 80% gravel over three days. A route stitched together by memory, maps, and a few lucky turns. But more than anything, it became an unexpected ride through the chapters of my own life here in Vermont.

Day 1: Waitsfield to Woodbury (42.6 miles, 4,967 ft)

Three miles in, we learned the hard way that bike lanes can hide surprises. A razor blade sliced through Suzanne’s tire, leaving us stranded before the trip had even begun. Luckily, Riders Outpost had their doors open. Luke set us up with a new tire and tube, got us rolling again, and just like that we were reminded how quickly this state shows up for you.

The first major challenge was Moretown Mountain—a grind that gave way to a rugged class IV road, part climb, part hike-a-bike, all adventure. From there we dropped into Montpelier for lunch before tackling an 8.5-mile climb with 1,500 feet of elevation gain through Adamant, Calais, and North Calais. Cool temperatures, perfect dirt, and even a barn that arched over the road like a tunnel made the miles feel familiar, like rediscovering trails from an old dream.

By the time we rolled into Woodbury, rain began falling, just in time to join the “WWW” (the Wild Women of Woodbury) for a birthday gathering. The WWW are more than just family friends; they’re the parents’ friends I grew up around, people I’ve known my entire life. They are the tightest group of friends I’ve ever met—bound by decades of memories, annual parties in Woodbury, and a deep sense of joy in welcoming others in. Walking into that gathering felt like stepping back into my childhood. Stories flowed as easily as the laughter, and even though years had passed, they instantly made me feel at home. The ride wasn’t just about distance; it was about coming home, and the bike was the perfect vector in getting us there.

Walking the bike down a classic VT Class IV road

Day 2: Woodbury to Zach Woods Pond (33 Miles, 3,100 ft)

The day began with an ambitious plan to climb Woodbury Mountain Road, a climb I’d always wanted to do. Over breakfast, the friends we stayed with filled us in on how beat up the road had gotten. They told us it was washed out and barely rideable, so we decided to steer clear. Instead of forcing a rough climb, we pivoted toward Hardwick.

There, we stumbled onto the Hardwick Rail Trail—a 3.8-mile stretch not even listed on Ride with GPS. It paralleled Route 14 but sat higher, a ribbon of quiet dirt that spilled into town with an effortless 473-foot descent. Coffee in Hardwick, lunch in Craftsbury, and dirt roads framed by open farms, cows, and fields—it all felt like the Vermont I knew growing up.

The real highlight of the day, though, was Bridgman Hill Road. Getting up high above the valley with epic views of the Green Mountains, all while weaving through open farmland, was unforgettable. That blend of mountain vistas and working landscapes is what makes Vermont’s gravel feel so alive.The general stores were part of that fabric too: places where you fuel up on sandwiches, pick up something sweet, and catch a glimpse of community life.

By golden hour we reached Zach Woods Pond. We swam, cracked open Hill Farmstead beers, and let the light settle across the water. That moment felt like pure Vermont: a peaceful pond at dusk, and a deep, grounding sense of place. We capped the night with a game of cribbage by headlamp before crawling into the tent early, ready for the long day ahead.

Day 3: Zach Woods Pond to Waitsfield ( 52 Miles, 4,000+ ft)

We woke before the sun rose. A thick layer of fog danced across Zach Woods Pond, the world still and hushed. I grabbed my camera and started running around the peninsula, chasing the light as it shifted and broke through the trees. Moments like this remind me why I document trips—the way fog bends the light, the stillness of morning, the magic that seems to exist only for a few minutes. Our little setup looked like something out of a dream: bikes geared up, our tent pitched by the water, mist rising in the background. A full bikepacking scene in one frame. I couldn’t have made it with AI if I tried, nature will always tell the better story.

After the photos, we packed up and took a quick swim at Green River Reservoir. That place became a lifeline for me during COVID, when the park wasn’t taking reservations and everything was first come, first serve. It allowed last-minute escapes, spontaneous overnight trips that fueled my connection to the place. Returning now by bike felt different. Harder earned. More connected.

The route carried us onto the Lamoille Valley Rail Trail, then into Morrisville for breakfast and coffee. The stretch to Stowe included the longest paved section, but it brought us to Brownsville Road, a gem of a climb that turned to rugged class IV and ended in a cow field. Vermont has a way of surprising you like that: steep effort, rough edges, and then beauty that stops you in your tracks. An espresso in Stowe, lunch at Pro Pig in Waterbury, and then one last surprise: a gravel road I hadn’t even known existed until a week earlier. It runs between Route 100 and 100B (Cobb Hill Rd), hidden and perfect, with a hike-a-bike section before reconnecting near Stevens Brook.

When I coasted back into Waitsfield, 124 miles later, I felt what I had been chasing all along. This wasn’t just a loop. It was a ride stitched together by memories, by people, by the places that made we understand why I love living in Vermont. A sense of home, rediscovered one climb at a time.

My Bikepacking Gear List:

Nelson's Biking Kit: