The High Road: An enchanting walking holiday in the Berkshires

In the Berkshires of Western Massachusetts, an alluring and less punishing alternative to traditional hiking is taking shape. The High Road, a new long-distance pathway, allows you to walk from village to village, passing through deciduous woodlands and traversing gusty ridgelines that offer breathtaking views of farms, ponds, and New York’s Taconic Range.

You can travel light, refuel at local restaurants, and spend the night at a cozy inn before continuing your adventure the next day. The High Road will eventually span the entire spine of the Berkshires. Its first section, running 10 miles from Pittsfield to Lenox, was unveiled in 2021. After two years of enjoying calming strolls against the backdrop of the pandemic, I decided it was time to treat myself to a more decadent “walking holiday” through these lush mountains where great American literature was born and where unique cultural experiences, like music festivals, take place.

A US-style Camino walking holiday

The concept of the walking holiday—a scenic journey where you eat and rest in towns along the way—is integral to the High Road. The Berkshire Natural Resources Council, the organization that created The High Road, found inspiration in Spain’s Camino de Santiago for their town-to-town path. The goal was to introduce people to a gentler, more accessible way of traveling across the countryside on foot. While The High Road passes over authentic mountains, the terrain never feels overly rocky or steep, and its immersive stretches through conservation woodlands are perfect for letting your thoughts roam freely.

Planning your High Road walk: no car needed

The High Road’s passage through Pittsfield and Lenox allows for easy trail access without a car. You can catch an intercity bus or train to Pittsfield from Boston or New York. Both towns are serviced by local buses, making the first section of The High Road accessible in a single day, with options to recharge at a nearby inn. If your feet are sore the next morning, you can take the bus back or continue exploring the area with alternative trails leading back to The High Road.

The journey begins in Pittsfield

I began my long walk at Dottie’s Coffee Lounge, a cozy spot in downtown Pittsfield known for its delicious baked goods. 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, but in the spirit of a walking holiday, I decided to walk three miles to the Bousquet trailhead. After stocking up on snacks, I set off on my trek, leaving the bustle of the city behind and embracing the serenity of nature.

Kicking off with a climb

The backbone of The High Road’s Pittsfield-to-Lenox section is Yokun Ridge, home to over 6,300 acres of preserved forests and wetlands. Blazed with orange trail markers, this section features a solid climb of roughly 700 feet elevation gain. Yet, with just a light pack and the promise of a hot meal waiting at the end of the day, it felt manageable. Approaching the ridge, I was rewarded with breathtaking views from Mahanna Cobble, where I enjoyed a panoramic vista of the undeveloped landscape.

Across the Yokun Ridge

After leaving the forest of Bousquet Mountain, The High Road levels out, winding through sunny patches atop Yokun Ridge. Cairns mark the path from Mahanna Cobble to one of the summits, Yokun Seat. Enjoying the beautiful scenery, I savored a moment of tranquility before continuing my ascent to Lenox Mountain, where the enchanting woods offered an escape into a magical atmosphere.

A meditative break in the journey

The descent towards Lenox felt more like a meditative stroll, following quiet roads through the woods. This serene environment allowed my thoughts to wander freely. After a rest beside Monks Pond, I encountered fellow travelers arriving for wellness classes at Kripalu, marking the end of The High Road’s first section. It was a perfect blending of nature and culture.

Sustenance begins with free champagne

While still en route, I enjoyed a final walk into the charming village of Lenox, arriving at a lovely boutique hotel. After checking in, I was welcomed with a complimentary glass of champagne enjoyed on the balcony, reflecting on my day. Later, dining on delicious pizza with local ingredients, I marveled at the communal atmosphere of the village as night fell.

From towns to trails

The High Road connects Berkshire towns while simultaneously linking residents with the natural beauty around them. This connection is exemplified by a detour I took back to Yokun Ridge the following day, allowing for exploration of local trails that lead to hidden gems within the forest.

Taking a detour

While the detour back to The High Road isn’t part of the official route, it allows for freedom and discovery. I ventured into a nearby plaza of shops and cafes, finding delightful local treats to enjoy. The High Road will eventually feature more trails leading to local eateries, enhancing the walking holiday experience.

The last steps

My shaded walk from Kennedy Park led me to Pleasant Valley Wildlife Sanctuary, where the final ascent to reconnect with The High Road was challenging yet rewarding. The views at the peak were moodier than the previous day, showcasing the beauty of nature on a walking holiday. This experience truly embodies the spirit of exploration and the unexpected journeys that come with each step.