Words and photos by Chris Case @chrisjustincase

Chris Case is a journalist, adventurer, and founder of Alter Exploration, guiding cyclists on transformative journeys in some of the world's most spectacular locations, including the Dolomites, Iceland, the Piedmont Alps, and Colorado. Formerly, he was the managing editor of VeloNews magazine and the editorial director for Fast Talk Labs. He is proud to be a Shimano ambassador.

Shimano Gravel riding

When the rough-hewn pavement ends and the dirt begins, the road becomes smoother, though a little softer. The loamy crunch of rubber on dirt is accompanied by the tweets of various songbirds lounging in the hardwood forest. We pass from sun-drenched to dark shadows in seconds, and the cool air brings sweet relief as it passes over beads of sweat.

Meadows of long, lush grass give way to thick maple trees, creating a canopy that arches over us like a living tunnel. Sunlight tumbles through the broad leaves of this deciduous forest. And then comes the moment we’ve been waiting for—the crunch of our tires on glassy dirt turns into thumps and thuds as we transition onto a ragged double-track. As the road ceases to be road-like, the question comes to everyone’s mind: “Um, can we go this way?”

If you roam in Vermont, prepare for this eventuality. If you’ve chosen a good route or decided to participate in a local race, it’ll come: That moment when you aren’t quite sure what you’re about to get into. You might question whether you’re about to start trespassing on someone’s private property or headed down a dead-end trail.

With a hesitancy in your pedal stroke but a flutter in your stomach, you’ll giddily ask, “Is this the way?!?” Yes, it’s the way. It will feel like sticking your hand in the proverbial cookie jar—of gravel roads. Keep riding. Take all the cookies and gobble them up.

Never Say Die

Roads don’t die in Vermont. They only get better with age—especially if you’re a gravel cyclist. To the outside world, Vermont might be best known for its maple syrup, fall foliage, and flannel. For those who love to ride gravel bikes, though, the state is famous for something much less refined: its raw dirt roads.

Vermont is home to 8,550 miles of dirt roads and boasts only 7,213 miles of paved roads, according to the Vermont Agency of Transportation. That's the highest ratio of dirt to pavement of any state.

Sixty percent of roads in the state’s remote Northeast Kingdom are unpaved; Caledonia and Essex counties, home to one of Vermont’s most famous gravel races, Rasputitsa, have nearly twice as many miles of dirt as pavement.

The abundance of primitive roads is due, in part, to the way they classify "roads" around here. In Vermont, any road that ever officially entered into a town's record books remained legally recognized indefinitely. It didn't matter if the road had been unused or abandoned for 200 years or if it was never completed in the first place. If it was surveyed and registered, it was a road, unless it was officially discontinued. Once a road, always a "road."

Many of these are the state's "ancient" roads. While recent changes to state law have altered some of these roads' designation, many remain in the rawest form.

Perhaps more famous are Vermont’s Class IV roads, which the state classifies as unmaintained public rights-of-way. Affectionately called Vermont pavé, these former logging roads, jeep trails, and other historic paths are often the most rugged, scenic, and, therefore, the most coveted by gravel aficionados. Unless explicitly prohibited by a landowner, they are ripe for riding.

These are Vermont’s finest.

Ode to stone

When exploring Vermont, you’ll eventually ride, or hike with your bike, through a lush, dense forest. Listen for the babbling brook. Be on the lookout for the small tubes that run from maple tree to maple tree—these collect sap that will later be turned into syrup to flavor your delicious maple creemee.

And be sure to scan the woods for those relics of early American determination and ingenuity: old stone walls. There’s a really good chance you’ll scratch your head, wondering why on earth there are so many of these dry-rock sculptures hidden deep in the woods.

It has to do with Portugal, Napoleon, and sheep.

In the early 1800s, Portuguese aristocracy tended prized merino sheep, and the Portuguese government kept a tight grip on the international market of this valuable product. Then, in 1809, Napoleon Bonaparte defeated the Portuguese, and the government was no longer able to enforce its embargo.

An American politician and former merchant, William Jarvis, saw a business opportunity and began importing thousands of sheep to his property in Weathersfield, Vermont. Being hearty foragers, merino sheep were ideal for grazing on New England’s rocky terrain. By 1840, it is thought that there were 1.7 million sheep in Vermont.

Farmers cleared vast swaths of forest to create pastures. Buried under thousands of years' worth of rich composted soil and old-growth forests, they found seemingly endless piles of rock. Naturally, the diligent farmer found a solution to solve two problems simultaneously. To rid the rocks from the fields, delineate property lines, and corral the animals, they made walls.

Eventually, nature has returned much of Vermont to its pre-sheep heyday. Trees and all manner of plant life have buried these walls beneath their canopies. And now it’s up to you to find these ruins of early American civilization and marvel at the awesome human achievement they represent.

Don’t worry, seemingly every dirt road in Vermont, whether near open pasture or nestled beneath a century of duff, offers a glimpse of these relics.

The humid air helps specs of dirt cling to our shins. It has been hours since we last saw any sort of moving vehicle, though we’ve gawked at a few dead trucks sitting in yards beside red barns and old homesteads. We count six stop signs on today's 6-hour loop. Long ago, we lost track of the number of bird calls that echoed through the forest. We won't soon forget the black bear that ran across our path.

Now, all we can think about is our final reward—something to be found only in this part of the world. Rides in Vermont, particularly in the summer, end best with a maple creemee in hand. Soft, silky smooth, with the sweetness of maple syrup, they beckon us to eat fast before ice cream spills over the cone in milky rivulets.

We sit on live-edge oak benches and kick our feet up next to the village bulletin board, filled with flyers for wood-cutting and stump-grinding services. We take as long as we can but not nearly long enough—maple creemees melt fast. And then it’s back to pedaling, pausing briefly at stop sign #7, quickly turning from town onto an aptly named road—something like Frost Hollow Trail or Cloudland Road.

Back to one last push over Vermont’s finest.


Best Town to Call Homebase

Even though it’s a small state, Vermont has a ton of great riding terrain. The state's south, central, and northern portions each have their own feeling and appeal. In the south, staying near the ski resort of Mount Snow in a town like West Dover provides places to eat, sleep, and drink after your rides. In the center of the state, the Mad River Valley is as wild as it gets, with a side of history. Up north, a town like Burke in the Northeast Kingdom provides a homebase for all manner of off-road riding.

Getting There

Burlington International Airport is the most convenient airport for those traveling to the central and northern parts of the state. Consider landing at Bradley Airport near Hartford, Connecticut, if you plan to explore the south.


Vermont is famous for its bed-and-breakfast culture. Book well in advance if you plan to travel during peak foliage season. Otherwise, there are good AirBnB and hotel options, particularly near ski resorts.

Time of Year

June through October is the heart of the best riding season. Go before May, and you'll get to play in the mud; visit after October, and you might be able to play in the snow—or mud. Of course, from mid-September until late October, depending on the year and your location, there are plentiful world-class leaf-peeping opportunities.

Key Equipment

If your focus is to ride everything, including the most rugged Vermont pavé, bring a gravel bike fitted with a minimum of 42mm tires (ideally, the bigger the better). If you’re sticking to the plush dirt, which can be smoother than pavement, an all-road or gravel bike with a 30-35mm tire would be plenty. There’s also a ton of great road riding, including the state’s six “gaps” across the heart of the Green Mountain range that are challenging and rewarding in their own right.

Be equipped with a large range of gears (at least a 1:1 low gear, but preferably more); the climbs will be steep and plentiful. Bring a bar bag or hydration pack to carry food and water; small villages can be few and far between, and some general stores have limited hours. If you have the option, consider bringing a compact water filter or filter bottle and replenish on the go.

During the summer, various bug species can get a bit pesky. Consider insect repellant, or plan on never stopping! In the fall, bring all the clothing, including a waterproof, durable, dark-colored jacket that will hide the mud spray.

Recommended Food Stops

Vermont is home to an incredible food culture. Whether it's small-batch cheese farms you fancy, craft beer you crave, or homegrown maple creemees you seek, the choices—not to mention the incredible flavors—are abundant.

Be on the lookout for many of these small, family-owned businesses, as they're often tucked away in inconspicuous settings. Vermont's unique road signs are often helpful in finding off-the-beaten-track attractions.

Must-Ride Route

Vermont is home to some incredible gravel races: Rasputitsa, Vermont Overland, Rooted Vermont, and the Guilford Gravel Grinder are a few of the state’s best. Their courses offer a perfect sampling from each respective part of the state.

For some of the best riding in New England, consider the Deerfield Dirt-Road Randonnee (D2R2), which traverses northern Massachusetts and southern Vermont. The event is described by many as one of the hardest, most beautiful, most traffic-free, most fun rides that they’ve ever done because it takes advantage of what that part of the world has to offer: the narrowest, oldest, twistiest, quietest, and most scenic roads available.

See my Strava of the Vermont Overland course

See my Strava of the D2R2 short course