Summer Street leading to Lee, Massachusetts (Photographer: Gabriela Herman for Bloomberg Businessweek)
My wife, Sigrid, and I are ardent road trippers. But over the years, we’ve often talked about seeing the world more slowly, ditching highways for cross-country footpaths such as the Transcaucasian Trail in Georgia or England’s Coast to Coast Walk. We’re more realists than romantics, though, so we always punted the idea. Who could predict how our legs would fare? Or our marriage? The trips remained perpetually relegated to the “someday” file, along with piloting a hovercraft.
Then a pair of books about epic walks was published in the spring of 2023. Neil King Jr.’s American Ramble, an ecstatic recounting of a 330-mile perambulation from Washington, DC, to Manhattan, made me realize I could pursue an itinerary without venturing as far as the Caucasus. And Walking With Sam, Andrew McCarthy’s sentimental tale of his 500‑mile pilgrimage along Spain’s Camino de Santiago with his teenage son, made me think walking for days could be a bonding experience, rather than the opposite. So the idea took hold again.
I reached out to McCarthy and asked for his advice. “Just go,” he said. And then said again. In less than four minutes he said “just go” no fewer than 10 times, in sentences and exhortations. Was his zeal endearing and maybe a little nuts? Yes, but also very persuasive. We were going. Not internationally; we didn’t have the time for that. But somewhere.
We found that while the US has some incredible hiking routes, including the Appalachian and Pacific Crest trails, opportunities for walking—where days end in a hotel or inn rather than a tent—are few. In most of the country, towns just aren’t clustered closely enough. My search led me to Mindy Miraglia, who in 2020 started a company that could bring the profound experience of Camino-style walking to the US—specifically to the Berkshires of western Massachusetts, where she lives.
She calls it Berkshire Camino, and through it she offers single- and multiday group walks in summer and fall. They typically run for five or six days and include downtime at upscale hotels and ambitious restaurants rather than the typical hostels and budget meals you’d expect on the Spanish trail. One offseason route Miraglia suggested sounded especially doable, at four days and just more than 50 miles, from Stockbridge to North Adams.
So we went.
We’d barely made it outside New York City when, on the Taconic State Parkway, my ancient Audi balked and lurched and lurched again. I wasn’t going to let the trip end before it began. After nursing the car to a nearby Amtrak station, I texted a woeful update to Miraglia.
“Remember …” she replied gnostically, ellipsis and all, as if delivering a fortune, “on a journey like this, trail angels intervene.”
High Lawn Farm (Photographer: Gabriela Herman for Bloomberg Businessweek)
An hour and a half later, there she was, picking us up at the train station in Hudson, New York. She dropped us near the Massachusetts border in Hillsdale, at Little Cat Lodge, a Swiss-style building with Alpine-chic interiors. We had time for a hearty schnitzel dinner and a good night’s rest. The next morning, right on schedule, we set off.
On our first day, we walked 15 miles from picturesque Stockbridge to the artsy town of Lenox, which by car (and without leisurely detours) would’ve taken 10 minutes. Miraglia had ferried us to our starting point. She also came along for the day to guide us over the roundabout route she’d cobbled together from country lanes and forest trails—combinations one could never coax from the hiking app AllTrails or get Google Maps to conjure. (Trust me, I’d tried.)
The back deck at Little Cat Lodge (Photographer: Gabriela Herman for Bloomberg Businessweek)
We carried all our belongings with us, though Berkshire Camino can shuttle them from hotel to hotel for travelers. I used a midsize Mystery Ranch Scree 32 daypack, while Sigrid wore a Jade 28, a smaller backpack made by Gregory. We’d chosen them for their supportive hip belts and weight distribution, which we could adjust with tensioning straps. Next time, we told ourselves, no laptops.
As we arrived in front of a stone grotto at the 350-acre National Shrine of the Divine Mercy, Miraglia asked us to “set our intentions” for the day. Mine was basic but sincere. I wanted to experience the tranquility that comes from having just one goal at a time: in this case, making it to Lenox. Sigrid kept hers to herself.
The first 7 miles hummed along. When we walked into Joe’s Diner for a lunch break, it felt like striding right into a Norman Rockwell canvas. (If we had more time in Stockbridge, we could’ve checked out his museum there.)
The diner, at the heart of the setlike town of Lee, is mythically depicted in The Runaway, the artist’s famous painting of a youngster on the lam. And although there were no bindle-toting boys sitting at the counter, I imagined that my lemonade and hot dog—on a griddled split-top bun—was exactly what a school-age escapee would’ve ordered.
Cows at High Lawn Farm, a 100-year-old dairy and ice cream maker (Photographer: Gabriela Herman for Bloomberg Businessweek)
The view from Kripalu Center for Yoga & Health, a beloved retreat in Stockbridge (Photographer: Gabriela Herman for Bloomberg Businessweek)
From there, the town gave way to pastures as we wound step by step toward the elaborately turreted, 100-year-old High Lawn Farm dairy, famous for its “farm to cone” ice cream. Walking gives ample opportunity for anticipation, to smell the grass munched by the herd of Jersey cows. It satisfies a craving many of us have these days, to move through the world in an immersive, sustainable way.
When an ice cream maker has the confidence to churn unadorned sweet cream, that’s the flavor you order. I sat down on a wooden bench, shed my pack and relished my choice. Nearby, a father was reading from one of Roald Dahl’s memoirs about his time as a World War II pilot to his two young sons.
We clocked seven hours of walking on our first day, but by the time we arrived at the Constance, one of a trio of recently refreshed Victorian inns run by the Lenox Collection, I was focused less on the ground we’d covered than the way each stop gradually came in and out of focus, giving small moments of time to sink in. There was the forest path lined with bloodroot flowers and scarlet elf cup mushrooms. The woman in pearls and a blazer taking out her garbage, who asked us if we’d happened to see a bear in the neighborhood. (No, thankfully.)
And the snaking line of people waiting to enter a tent with a sign reading “Confession Confession,” which served as a real foil to the magnificent formal gardens that led us to Edith Wharton’s mansion, the Mount.
To my great surprise, after our arrival in Lenox, I was still eager to explore. So, despite a surfeit of fine dining options within blocks of our hotel, I proposed dinner with a side of live music at the Apple Tree Inn on the outskirts of town. “What’s another 2 miles?” I asked my wife, when Uber turned up blank. She looked at me as if I’d lost my mind.
I have no regrets. The Arts and Crafts-influenced Ostrich Room lounge was beautiful; the food, rib-eye with chimichurri, delicious; and the band, Clare Maloney & the Great Adventure, captivating. When I finally found a car for the way back to the hotel, it was $50: comically expensive, but absolutely worth it.
High Lawn’s perfect pit stop—ice cream (Photographer: Gabriela Herman for Bloomberg Businessweek)
The summery weather and surprisingly easy walking came to a chilly, soggy halt on Day 3. When we woke up at the Hotel on North in Pittsfield, it was raining, the temperatures were stuck in the 50s, and—despite my wearing well-broken-in Danner Logger boots—I’d gotten a blister on my big toe.
It all conspired to make the smooth, flat ribbon of the Ashuwillticook Rail Trail, which runs 12.7 miles from Pittsfield to Adams, feel like a slog. Under my breath, I uttered a prayer for a trail angel to deliver us to our next overnight stop, the Colonial-era Harbour House Inn in Cheshire. It went unanswered, and I barely said a word over the 28,795 increasingly painful steps my Fitbit said it took to get there.
I’ve never been more happy than I was on arrival, sitting in a cushy wingback chair in the cozy Pinterest-Victorian parlor, proffered just-baked oatmeal cookies. By the time I signed my name in the guest book the next morning, blister lanced and bandaged, I was eager to take on the final leg of our journey: a proper hike to the industrial-town-turned-art-hub of North Adams, via the 3,491-foot-high summit of Mount Greylock.
Berkshire Camino’s summertime itineraries call this literal high point a time to celebrate and reflect. But on our trip, late-season flurries began about halfway up; at the summit, the temperature hovered around freezing, the majestic views hiding behind a curtain of clouds. “Things will happen,” I reminded myself as we snarfed down some power bars and headed toward North Adams.
The Apple Tree Inn, on the outskirts of Lenox, is worth dinner and a show... (Photographer: Gabriela Herman for Bloomberg Businessweek)
...or a stay overnight. (Photographer: Gabriela Herman for Bloomberg Businessweek)
Our quads ached. On a whim, I turned around and headed backward down the mountain to let other muscles do the work. Sigrid took my hands to help me avoid stumbling, then let go to spin around herself. It felt silly but sublime, the two of us walking backward down the mountain, snow falling gently around us. But somehow it was every bit as meaningful as any summit celebration. In that moment, I got my first glimpse into the subtly mystical and transformative thing that happens after a few days of walking.
By the time we reached the empty trailhead parking lot, 12 miles and a few thousand feet in elevation change from the morning’s departure, I was feverishly dreaming of putting my feet up at the eclectic new Hotel Downstreet in North Adams, an additional 2 ½ miles downhill. Maybe I’d also polish off a raft of the miniature frankfurters that nearby Jack’s Hot Dog Stand has been slinging since 1917. I’d walked enough.
Just then, a small SUV whipped into the parking lot and stopped. The driver rolled down her window. “Where are you going?” Downtown, we said. “I’ll take you.”
Maria, as she introduced herself, hopped out and opened the trunk for our bags. Sigrid and I looked at each other, both to confirm that this really was happening and for a gut check: Were we really going to get into a car with a stranger in the woods? Yes. “The Lord sent me,” Maria said, pointing to the sky as she closed the hatch.
As it turned out, Maria, who appeared to be in her mid-40s, had run up and down Mount Greylock every week for years while training as a track-and-field athlete. She knew what sore feet felt like.
Driving at 35 mph felt like warp speed. I was amazed how quickly my brain had adjusted to expecting the world to pass by at a walking pace. My wife and I had made a small dent in the map under our own steam—and still liked each other enough to consider doing it all again, somewhere else. And although we’d been skeptical about the mysticism and fervor that both Miraglia and McCarthy had described before our trip, now we bought into it.
When we arrived at the hotel, I tried to offer Maria money for the ride. She adamantly refused. And just before leaving, she justified it: “I’m your angel.”