By Jamie James

My roommate Jonathan promises that tonight 
we will see history being made: The Who is performing Tommy, our favorite band’s genre-bending rock opera, at Tanglewood, just off Route 7 in the woodlands of Western Massachusetts. It’s a hot day, this July 7, 1970.

Jonathan and I have been here since midmorning to stake out a spot on the lawn, the cool place to be, just behind the covered shed at this Berkshires landmark where the Boston Symphony Orchestra makes its summer home. Frisbees are flying in the breeze, and so is the shoulder-length hair of the mostly male fans.

As the golden haze of midsummer deepens to a violet twilight, the Who finally takes the stage. The crowd jumps to its feet and cheers. Pete Townshend leaps around like a mad cricket, Roger Daltrey tosses his microphone high into the air, and when the overture to Tommy begins, I can feel Jonathan’s prediction coming true.

Forty-some years later, that night endures—if only in HD and hyperbole by aging fans like me.

Route 7 runs through the main street in Great Barrington, and is a popular gathering spot for events such as the antique auto show. (Photograph by Jodi Hilton)

Route 7 runs through the main street in Great Barrington, and is a popular gathering spot for events such as the antique auto show. (Photograph by Jodi Hilton)

I’m driving north through Berkshire County, returning as a guest lecturer to Williams College, my alma mater, just shy of the Vermont state line. It’s New Year’s Day, two days after a deep snowfall, and the broad-shouldered, smoothly curving highway is nearly empty of traffic. But the rearview mirror of my mind is all swirling stage lights and marijuana smoke, twinkling fireflies and thundering bass lines.

I follow Route 7 along the Housatonic River, as the road wraps around hills cloaked in evergreen forest. The river is frozen in wide, white sheets, punctuated by intense rapids where the rocks poke through. On my right, steep cliffs of dark purple granite hover overhead, dripping icicles thick as a man’s leg. The morning light picks out tiny rainbows in the ice and intense golden gleams from veins of quartzite. Even in the austerity of winter, retracing this trail of youth brings fading memories into vivid focus.

Following my meditative ramble through wilderness, it’s almost a shock to find civilization when I roll into the town of Great Barrington. In my college days, the only place to stop here was Alice’s restaurant, made famous by Arlo Guthrie’s folksy musical monologue of the same name.

Alice has moved on and her restaurant is long gone, so I pull over at the Home Sweet Home Doughnut Shoppe. The name is ye olde hokey, but at least it fits the place, which occupies the ground floor of a two-story frame house, white with red shutters. The coffee is fragrant and strong; the classic glazed doughnut about perfect.

I pay my bill and chat with the pop of this mom-and-pop business. A Connecticut native, John Scalia moved here in 2009 with his wife, Debbie, after their children flew the nest. “Business is booming around Northampton, but it feels too urban,” he explains. “We liked the vibe in Great Barrington, so we opened shop here.”

Three kinds of apple cider donuts at Home Sweet Home Doughnut Shoppe (Photograph by Jodi Hilton)

Three kinds of apple cider donuts at Home Sweet Home Doughnut Shoppe (Photograph by Jodi Hilton)

The Scalias’ doughnut spot may be new, but it’s typical of the Berkshires that I remember. You see few national chains and franchises; here most businesses have names like Tom’s Toys, Steve’s Auto Repair, the Mountain View Motel.

I’m on the road again, recharged by sugar and the primeval chords of “My Generation” on the Who mix I downloaded for the drive. I’m making some progress in my attempt to feel like a kid. I slide around a curve in the road and come abreast of a regional middle school. I know just where I am, and pull off the road to admire the Devil’s Pulpit.

My mind slips back to the day after college graduation: barreling down Route 7 to meet some friends from Simon’s Rock, the “early college” where first-year students enroll as early as 16. Nathan, Mimi, and I planned to picnic on nearby Devil’s Pulpit, a rock pillar that looms over the Monument Mountain nature preserve on the northern outskirts of Great Barrington. When we got to the park entrance, gray clouds lowered ominously. I pointed to the sky, saying, “Looks like rain.”

“No problem,” Nathan replied, shrugging. Nothing was ever a problem for Nathan. “We can always find a cave or crag to sit under.”

We chose the steeper path, where the trail follows a cut in the rock, thickly wooded with evergreens and a few stands of oak and maple that were then in full leaf, a brighter green. The forest shaded a tapestry of wildflowers, accented by flashy pink lady’s slippers. Where the trails converge, Inscription Rock, a flat boulder with an elegantly carved epigraph, claims the mountain for “the people of Berkshire as a place of free enjoyment for all time,” dated October 19, 1899.

The rough-hewn granite steps of the trail wind just below Squaw Peak, the highest point, to the Devil’s Pulpit, a dizzying column with a view almost to Vermont, nearly 40 miles away. The prospect takes in a few church steeples and smokestacks along the curling ribbon of Route 7, but mostly it’s an undulating sea of forest. Just as Mimi had opened the picnic basket, a light rain began to fall. No problem: As Nathan foresaw, an overhang nearby proved just wide enough for a cozy picnic.

Now, as I gaze up at the Devil’s Pulpit from the roadside, a lecture from an English course I took at Williams struggles up to the surface: When Nathaniel Hawthorne was living in Lenox and Herman Melville in Pittsfield, the two men met for the first time on a climb up Monument Mountain with some friends.

A hiker looks out from the Devil's Pulpit on Monument Mountain, which overlooks the countryside of neighboring states Vermont and New York. (Photograph by Jodi Hilton)

A hiker looks out from the Devil’s Pulpit on Monument Mountain, which overlooks the countryside of neighboring states Vermont and New York. (Photograph by Jodi Hilton)

Caught in a thunderstorm, they sat together under a rock—perhaps the very place I picnicked with Mimi and Nathan. The two writers brainstormed for hours, the beginning of a close friendship. Some scholars say this encounter sparked Melville’s novel about a man’s demented quest of a great white whale: Moby Dick, the first and still a leading contender for the title of the Great American Novel. He dedicated the book to Hawthorne.

Four decades later, judging by what I’ve seen on the ground, the view from the Devil’s Pulpit must look much the same. There’s a good reason why Berkshire County has kept its wilderness: Fully one-third of the land is permanently protected from development.

Even if it’s your first visit, Main Street in Stockbridge may seem familiar. Norman Rockwell called the town his home for 25 years and described it as “the best of America, the best of New England.” In 1967 he completed a sweeping portrait of the south side of the street at Christmastime.

The eight-foot-long oil painting holds court at the Norman Rockwell Museum, just off Route 7, and showcases Stockbridge’s collection of intact architecture—the redbrick town offices under a Dutch stepped roof (now a candle shop), the neoclassical bank, and the baronial Red Lion Inn, fronted by a porch lined with tall rocking chairs.

I stop for lunch at the Red Lion. I’m not surprised to see that most of the menu hasn’t changed in decades, and the long dining room, embellished with lace curtains and shelves full of fanciful antique teapots, looks as if it hasn’t changed in a century. I order the famous native turkey dinner with all the trimmings. Served on Blue Willow china, the thick slices of turkey are moist, the dressing nutty—all smothered in a comforting blanket of gravy.

Tanglewood, just down the road, west of Lenox, is closed for the winter, but I make a quick detour to have a look. I park on the road and hike across the parking lot, deep in snow. The lawn slumbers under a flawless mantle of powder, gleaming bluish in the shade. Slanting afternoon sunbeams highlight a row of icicles running along the eaves of the entrance gate, like a blindingly bright pipe organ.

Next summer’s program is posted: Tanglewood long ago banished hard rock in favor of classical and jazz. As I return to Route 7, I defiantly test the limits of my car speakers with my Who mix.

The risk in taking a sentimental journey is that the places you want to revisit may have vanished, but when I get to Pittsfield I have the opposite experience. I think back to the crisp fall day I drove in search of Melville’s house, where he wrote Moby Dick. I had found 780 Holmes Road easily enough, an 18th-century white farmhouse with a bronze eagle over the door, like a thousand houses in the Berkshires. A sign in the driveway had warned: private.

Norman Rockwell's depiction of Stockbridge at Christmas time (Photograph by Jodi Hilton)

Norman Rockwell’s depiction of Stockbridge at Christmas time (Photograph by Jodi Hilton)

These days Arrowhead, Melville’s home, is open to the public as a museum, and I’ve been eager to make a return pilgrimage. I discover the house has been painted mustard yellow, the original color, and filled with sturdy wood furniture of the type that was here when Melville owned the place.

A mammoth chimney, velvety black with centuries of soot, dominates the ground floor. Melville wrote a story about this chimney. The volunteer tour guide, an enthusiastic local woman, explains that after Melville moved out, his brother Allan carved a few lines from the story in the chimney. Tracing the engraving in the blackened stone, she reads the first sentence aloud, “I and my chimney are settling together.” She grins. “Isn’t that neat?”

Upstairs, through the window of his study, I take in the postcard view of snow-frosted Mount Greylock, the highest point in Massachusetts. The guide says that this view inspired the tale of the great white whale. I consider mentioning the alternative creation story, that the novel’s genesis was Melville’s literary summit with Hawthorne at the Devil’s Pulpit, but decide against it. I don’t want to offend the guide.

By the time I hit Williams, I’m deep into the strangely beautiful fable of Tommy. As “Pinball Wizard” booms, the lawn of my alma mater extends before me. The federal-style wedding cake of the president’s house tops the hill in the mid-distance; beyond it rise the gray Gothic spires of the college chapel. I won’t say that I feel 18 again, exactly, but cruising in on Route 7 sure feels like a homecoming.

A few days later, wandering the galleries of the small, internationally renowned Clark Art Institute, I pause in front of one of my favorite pictures, Winslow Homer’s oil painting of two mountain guides. I can almost feel the wind on my face. Immersed in fall foliage, one man is grizzled, the other fresh-faced—a dichotomy not lost on me as I contemplate my own coming-of-age in this place, stuck in time in so many ways.

This feature, written by Jamie James, originally appeared in the February/March 2014 issue of National Geographic Traveler. Based in Bali for the past 15 years, James is also the author of several books, including The Snake Charmer.

Photographer Jodi Hilton splits her time between Boston and Istanbul. 

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