In the Berkshires of Western Massachusetts, an alluring and less punishing alternative to thru-hiking is taking shape. The High Road, a new long-distance pathway, allows you to walk from Berkshire village to village, passing through deciduous woodlands and traversing gusty ridgelines that offer views of farms, ponds, and New York’s Taconic Range.
You can travel light, refuel at restaurants and spend the night at a cozy inn before pushing onward the next day.
The High Road will open in pieces and one day span the entire spine of the Berkshires. Its first section, running 10 miles from Pittsfield to Lenox, was unveiled in 2021. And after two years of taking long, calming strolls against the backdrop of the pandemic, I knew it was time to treat myself to a more decadent “walking holiday” through the lush mountains where Herman Melville penned Moby Dick and where Wilco launched the Solid Sound music festival at Mass MoCA.
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The High Road in the Berkshires © Miles Howard
A US-style Camino walking holiday
The concept of the walking holiday—a scenic foot journey on which you eat and rest in towns along the way, carrying little but a change of clothes, water and snacks—is integral to the High Road. The Berkshire Natural Resources Council, the land stewardship organization that created The High Road, found inspiration in Spain’s Camino de Santiago when fleshing out plans for their own town-to-town path.
The idea was to introduce Americans to this gentler, more accessible mode of traveling across the countryside by foot. While The High Road passes over bonafide mountains, the terrain never feels too rocky or steep. And the path’s immersive stretches through conservation woodlands are the perfect place to let your thoughts run wild and free.
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The starting point for Berkshires’ The High Road © Miles Howard
Planning your High Road walk: no car is needed
The High Road’s passage through Pittsfield and Lenox makes it possible to access the trail without a car. You can catch an intercity bus or train to Pittsfield from Boston or New York. Both towns are also serviced by Berkshire Regional Transit Authority buses. From Pittsfield, you can complete the first section of The High Road in a single day, spending the night at a Lenox B&B.
If your soles are tender the next morning, you can catch the bus back to Pittsfield. But if you’re determined to walk on, there’s a more interesting alternative to backtracking the entire way. A selection of linked trails through nearby Kennedy Park and Mass Audubon’s Pleasant Valley Wildlife Sanctuary allows you to loop back to The High Road as it crosses the top of Lenox Mountain. This detour back to the official route is depicted on the BNRC’s High Road map.
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Markers on the trail of The High Road © Miles Howard
The journey begins in Pittsfield
I prepared for my long walk at Dottie’s Coffee Lounge, an aromatic joint in downtown Pittsfield with artwork on the walls and cheddar scallion scones the size of a baby’s head. The official trailhead for The High Road is at Bousquet Mountain ski resort on the south side of town. (Hiker parking is available at the resort.) The High Road will connect directly to downtown Pittsfield in the years ahead. But in the spirit of walking holidays, I decided to walk 3 miles from Dottie’s to the Bousquet trailhead.
After stocking up on beef jerky and seasoned nuts at the Berkshire General Store, I warmed up with a lively amble past the traffic on South Street. The storefronts and traffic lights receded and suddenly I was wandering past cottages and leafy estates, following South Mountain Road and Tamarack Road to the foot of Bousquet Mountain. Here a High Road trailhead kiosk beckoned beside the vacant ski lifts.
A chance to relax and look out over the Berkshires on The High Road © Miles Howard
Kicking off with a climb
The backbone of The High Road’s Pittsfield-to-Lenox section is Yokun Ridge, which boasts over 6300 acres of preserved forests and wetlands, as well as several defined summits. Blazed with orange trail markers, The High Road approaches the ridge by switchbacking up the wooded haunch of Bousquet. It’s a solid climb with roughly 700 feet of elevation gain. But with my light daypack and the promise of a shower and a hefty dinner at the end of the day, it somehow felt less cumbersome.
As I approached the ridge, I was rewarded with a breathtaking mountain overlook (and a stone bench) at Mahanna Cobble. While The High Road visits several vistas, the view from Mahanna Cobble consists entirely of undeveloped lands: a rolling, rustling sea of trees and nothing else.
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Cairns that help to mark the route on The High Road © Miles Howard
Across the Yokun Ridge
Leaving the forest of Bousquet Mountain behind, The High Road partially levels out and snakes through sunnier patches of yellowy tall grass atop Yokun Ridge. Piles of rocks (called “cairns”) mark the path from Mahanna Cobble to Yokun Seat, one of the Yokun summits. From here, I gazed west to the blue expanse of Richmond Pond, savoring the breeze and a fistful of nuts.
The gradual ascent to Lenox Mountain—the high point of The High Road’s first section—took me back into the woods. But the thin boreal trees and mosses that grow at higher altitudes give this section of The High Road an enchanted atmosphere. I half-expected to see elves pop out from behind a boulder as I made the final push to the Lenox Mountain lookout.
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Walking through the woods on The High Road © Miles Howard
A meditative break in the journey
If climbing the Yokun Ridge feels closer to a hike, the long and merciful descent toward Lenox is more of a meditative stroll. Following little-used dirt roads through corridors of oak and beech, The High Road widens and smoothens. Here I let my thoughts wander from the metaphysical (“what if all of mankind has one collective soul?”) to the elemental (“what kind of beer should I have tonight?”)
After finishing the last of my jerky beside the glassy waters of Monks Pond, I felt the mileage in my ankles. But the sound of other people—the first I’d heard since Bousquet!—quickened my pace. After crossing an active paved road and descending some wooden stairs into a more spacious pocket of forest, I found myself on the grassy campus of Kripalu, watching fellow travelers arrive for yoga classes. This marks the official end of The High Road’s first section.
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A bridge on The High Road © Miles Howard
Sustenance begins with free champagne
I wasn’t in Lenox village yet, but a final 1.5-mile walk along West Street took me from Kripalu’s gates past the Tanglewood Music Center and into a hilltop hub of red brick buildings and historic Victorian-style homes. Upon checking into The Constance, a lovely boutique hotel steps away from the village center, I was offered a complimentary glass of champagne and enjoyed it on the balcony, my walking shoes and legs still caked with dirt and mud from my High Road traverse.
Hours later, showered and coiffed, I sat in an Adirondack chair beneath twinkling lights outside Pizzeria Boema, digging into a wood-fired pie heaped with fresh arugula, pepperoni and a hot honey drizzle. With a piney pale ale by my side, I watched friends and families laugh and eat against the purple dusk and the surrounding dark woods from which I had emerged earlier.
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From towns to trails
The High Road is an alluring destination for visitors, but it’s also a way of connecting Berkshire towns and their residents to local wild spaces. This is exemplified by the alternate detour back to Yokun Ridge, which I committed to taking back to Pittsfield the next day, after assessing my energy and wolfing down a spinach and onion confit omelet on the flowery patio at Haven Cafe.
A simple 0.8-mile walk past a large cemetery on Main Street took me to Aspinwall Road and the south gateway of Kennedy Park, where a labyrinth of groomed paths and carriage roads takes you into hardwood forests. Just like that, I had gone from town to trails once again.
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Grabbing lunch just off The High Road © Miles Howard
Taking a detour
Since the detour from Lenox back to The High Road isn’t part of the official route, you have some freedom on where to wander. Not quite sated by my omelet, I decided to take a page out of Lord of the Rings (a narrative about an epic walking holiday) and enjoy a second breakfast. I followed the Woolsey path from Kennedy Park into a nearby plaza of shops and cafes, where I procured a beautifully-sculpted chocolate dog and some truffles from the Chocolate Springs Cafe.
The High Road will one day include more tributary trails that offer direct access to nearby outlets for grub and local goods. But it will also offer more opportunities for people to stumble across The High Road by accident. Watching shoppers at the Chocolate Springs Cafe, I wondered if any of them knew that you can walk here.
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Mass Audubon’s Pleasant Valley Wildlife Sanctuary in Lenox, Massachusetts © Miles Howard
The last steps
A shaded walk up a dirt road from Kennedy Park took me to Pleasant Valley Wildlife Sanctuary, where the final push back to the High Road route became more of an ascent. After passing a reedy pond, I wheezed my way up the flank of Lenox Mountain, admiring several laurel plants along the way, and re-emerged onto the familiar peak. But with more thunder clouds overhead this time, the view felt moodier and more austere than it had the prior afternoon.
That’s the beauty of a walking holiday. Whether it’s the color and character of the countryside or the offerings of settlements along the way, you’ll never know exactly what you’re walking into. I braced for thunder for the final leg of my walk, from Lenox Mountain back to Bousquet. Instead, I made a juicier discovery. The ski resort’s in-house restaurant, Lift Bistropub, had just opened. I was the first diner to arrive. With nearly 20 miles of walking under my belt, I sat out on the deck, and ordered the mushroom burger, contemplating the road I’d traveled…and the road to come.
You should try it sometime.