Word in these parts has it that Herman Melville was the one who named October Mountain, the centerpiece of Massachusetts’ largest state forest and the geographic heart of Berkshire County. Leave it to a literary man to get it right. In its eponymous month, the mountain’s line of folded foothills tumbles down from a pinched peak in a mosaic of reds, oranges, and yellows. Nearer at hand, a lazy river goosenecks through an undulating valley speckled with flaming sugar maples and a fringe of crimson sumac. And on this sunny October afternoon, I’ve got all this practically to myself; only a few kayakers sliding their boats into the water share the scene. I head up a dirt road into the highlands, as yellow leaves float down through a tunnel of beeches. Climbing the flanks of the mountain itself, only the occasional cry of a bluejay and the crunch of leaves beneath my feet break the silence.
For many visitors, “the Berkshires” means summer—and a straight run down U.S. Route 7, that familiar string connecting the cultural pearls of the Williamstown Theatre Festival, Shakespeare & Company, and Tanglewood. Come fall, though, a quieter region emerges, full of its own beauty and creativity—and nowhere is the season more spectacular than along Route 8, the twisting state road that parallels its tamer and more popular counterpart on the other side of Melville’s beloved hills. Now a new generation of artists and artisans are populating these pockets, far from the foliage tour buses.
And that’s exactly where I began my journey early this morning, after a delightful stay at the Topia Inn in Adams. At this self-described “eco B&B,” founded by a dancer and a musician, you’ll find, among other themes, a Zen room with certified sustainable-wood flooring, and organic rice-paper calligraphy over the bed; an Iroquois room, with a deep-shag organic-wool throw carpet and Native American log-drum side tables; and a French room, featuring a decadent silk-upholstered headboard and antique chair.
Everything here is natural, from the bath products to the forced steam used to clean without chemicals. “We wanted to be luxurious and show that you didn’t have to sacrifice to go green,” says co-owner Caryn Heilman, a dancer who performed for a decade at Jacob’s Pillow before settling here. Heilman traveled with her dance company all over the world, but fell in love with the beauty of the Berkshires.
“Most of the time we were in large cities, hermetically sealed in concrete, inside and out,” she says. “Here, it’s connected to the rest of the world artistically, but it’s also naturally remote. You can experience culture in a deeper, more relaxed way and add to your work in ways you wouldn’t have otherwise.”
In the morning, I set out south down Route 8, a winding road that hugs the base of the mountains through tight valleys lined with sugar maples and beech trees. I stop at a farm stand to pick up a half-peck of McIntoshes and admire the scenery with the tangy taste of fall in my mouth.
The mountains here are the oldest in New England—ancient compared with the wilder adolescents of Vermont and New Hampshire—their peaks mostly tamed and worn down over millions of years. But what they lack in grandeur they make up for in a kind of protective intimacy. Theirs is a manageable wildness; often, the hills are more felt than seen, a steady presence that provides more of a portrait than a landscape view of their surroundings. But it’s a landscape no less beautiful in the valleys, full of picturesque red barns and rusting farm equipment, framed by the comforting bulk of the mountains.
About 15 miles past Adams, Route 8 joins Route 9 and heads east toward Dalton. But first, with Melville in mind, I’ll take a short detour west toward Pittsfield, the “Brooklyn of the Berkshires,” the county’s bustling commercial hub that today is reinventing itself as a center of western New England art and culture.
For years here in pockets of the Berkshires, industry went hand in hand with nature, and the area flourished, with mills and factories taking advantage of ample lumber and fast-flowing rivers. Nowhere is this more apparent than in Pittsfield, a city whose history has traced the rise and fall of the Industrial Revolution in New England.
The architecture is as impressive as that of any small city in America, all granite and flourishes, even if the community struggled after its main employer, General Electric, all but left in the 1980s. Pittsfield has pinned its renaissance on attracting a creative class of artists and knowledge workers to the region, who come for the culture and stay for the natural beauty. If the new sushi restaurants, wine bars, and art galleries that have opened up downtown are any indication, that strategy is working.
It won’t be the first time that artistic types have found a home in the region. Attracted to the area for its natural beauty, Herman Melville bought a farm near here and reimagined the lines of the hills as the back of a sperm whale. This towering figure of American literature lived in Pittsfield for 13 years, gathering a literary community around him in his house on the city’s southern outskirts, where he finished Moby-Dick.
His home, Arrowhead, is now a history museum—but in some ways a more intimate view of the famous author may be found in the boxy downtown library, grandly called the Berkshire Athenaeum. There in the library’s small Melville Room, I discover the unlikely attraction that’s brought me here: a treasure trove of Melville memorabilia, including, among other items, paddles carried home from his South Seas expeditions; personal items, such as his pencils and his pipe and snuff box; and the desk from his New York home, where he wrote Billy Budd, his last prose work.
On the road again, it’s just a short backtrack to Dalton, where I make my way to Crane & Co., which produced the first paper for U.S. currency, more than 200 years ago. Today it still makes the cotton stock on which our dollars are printed, along with fine stationery. The Crane Museum of Papermaking, open weekdays from June through mid-October, is housed in the former rag room of the company’s Old Stone Mill, on the banks of the mighty Housatonic. Inside, stout oak beams arch overhead and tall windows illumine the floor; cases of 19th-century tools and other exhibits trace the long history of the craft in this valley.
Wending my way down Route 8 into Washington, I head west on back roads, past Ashley Lake and Sandwash Reservoir, deep into October Mountain State Forest and that glorious afternoon of hiking where our story began. After all that rugged exercise amid awe-inspiring natural beauty, it’s no wonder I’m feeling in need of some invigorating creature comforts.
If there’s a clubhouse for this quieter season, it’s the Dream Away Lodge, just down County Road in Becket. As I drive up the flank of Becket Mountain, at the southern end of the state forest, the restaurant seems conjured up as if by magic. One minute, I’m heading up a steep road that rises long enough to make me doubt my GPS; then, out of nowhere, the bright aura of a rickety farmhouse materializes by the roadside, with a splash of Christmas lights over the entrance and a parking lot packed with cars.
Rumor has it that the place was once a speakeasy or a brothel—and if it wasn’t, it should have been. A naked Marilyn hangs over the hostess stand, where a dark-haired woman insists that I sit in the bar area, since “it’ll be more fun.” Right after I settle in, a gray cat named Bob Dylan jumps up beside me, and together we watch a parade of jeans, flannel, and tattoos stream by.
The roadhouse’s claim to fame is that Dylan’s Rolling Thunder Review rolled through here back in 1975, with Arlo Guthrie, Joan Baez, and Allen Ginsberg in tow. The décor is so eclectic that it takes on a kind of symmetry: patterned tablecloths, random paintings and photos, tassled lamps, and Buddhas. The menu, created by chef Amy Loveless, is just as wide-ranging, from duck vindaloo to enchiladas—but the dishes are no mere larks. For an appetizer I’m served a pillowy chèvre from nearby Monterey, accompanied by a firm house-made guava paste, adding the perfect note of sweetness to the salty goat cheese. It’s followed by a well-marbled ribeye, expertly blackened, topped with chipotle sauce.
I rest contentedly as folk music drifts in from the wood-paneled lounge next door. Tonight’s act features Annie Guthrie—granddaughter of Woody and daughter of Arlo—and Bobby Sweet, a twangy singer/songwriter whose voice lives up to his name.
And so, with plaintive tunes lingering in my head, I find a home for the night just a few miles east at Canterbury Farm, a comfortable B&B set amid lush display gardens and 22 miles of hiking trails, on a historic property first settled in 1780.
In the morning, I’m back on Route 8 and heading down to its junction with Jacob’s Ladder Scenic Byway, a woolly stretch of U.S. Route 20 that one might imagine was named for the Biblical stairway to heaven, as romantic an environment as any 19th-century novelist ever created. It takes me west toward Lee (paralelling I-90), where I pick up Tyringham Road, south again. The hills here are smaller than those up north, but the landscape is covered with wildflowers; cows meander around brooks, as in a fairytale landscape.
As if reading my mind, the road suddenly brings me up short next to a bona-fide gingerbread house, appearing before me like Brigadoon. Piles of stones form parts of the walls of an undulating cottage, along with intricate stained-glass windows and thousands of shingles pouring down from the roof like so many stacked Keebler cookies. In the 1920s, English sculptor Sir Henry Hudson Kitson, most famous for his Minuteman statue on Lexington’s town green, transformed an old barn into his dream cottage studio, called Santarella. He spent every penny he could spare adding to his creation here over 25 years.
As I stop in, the owners, California transplants Dennis Brandmeyer and Denise Hoefer, who have been slowly restoring the house over the past nine years, are preparing for a wedding. They manage more than a dozen ceremonies a year here, most of them out back near a pond surrounded by pink burning-bush shrubs, whose teardrop leaves flutter to the ground as we tour.
The cottage itself had been neglected for years, used as a party house by neighborhood teens, and with a bat colony inhabiting the Rapunzel-like tower out back. Using materials as close to the original as possible, Brandmeyer transformed that tower into a weekend rental, complete with conical ceiling and white-canopied bed. (A second “silo” in another studio is also available, as is a four-bedroom Colonial house on the property.) “I’ve always been into fixing up old stuff,” he tells me. “On our bucket list once the kids were gone was a historic-preservation project. It’s cool to finish this thing this guy started 100 years ago.”
As we stand outside admiring the house, a truck slows down and stops—a regular occurrence among motorists not expecting to find this architectural jewel on the back roads of a quiet village. My next destination, about 10 miles away: Rawson Brook Farm, home of “Monterey Chèvre,” which I sampled at the Dream Away the previous evening and which has fast won acclaim as one of the best fresh goat cheeses in America. Like many regions, the Berkshires has embraced the local farm-to-table movement, and young folks are once again producing artisanal wares. Some farms, like Rawson Brook, have even begun to reverse the trend, earning renown far from their fields of production.
Turning west on Route 23, I pick up New Marlborough Road just outside downtown Monterey, and head south again. The farm is located up a steep mountainside in what might be generously called a clearing in the dense forest—but it’s enough to support some 45 goats. Though petting is allowed, this is a working farm; signs warn against feeding the animals, despite the attempts of a friendly black-and-white kid named Junonia to nibble on my watch and sweater sleeve.
While I’m there, owner Susan Sellew drives up, and I take the opportunity to ask her what makes her cheese so good. I’m not often a fan of goat cheese, which tends to be too “barnyardy” for my taste, I tell her, and I’m surprised to find that Sellew agrees with me. The trick, she says, is to cool the milk fast without jostling it too much, which can burst the fatty acids, releasing that musky flavor. (Jostling the finished cheese itself doesn’t affect the taste or quality.)
Enlightened—and pretty hungry—I continue west on Route 23 to the town of Great Barrington for dinner. Though you couldn’t really call this lively town off the beaten track, it’s better known to New Yorkers than New Englanders; they stop here on their way to Tanglewood to shop its boutiques and to pick up gourmet picnic supplies along Main Street. Its real draws, however, are its restaurants; to satisfy the summertime culture mavens, the town has fostered an unlikely yet bustling fine-dining scene amid mill buildings that, like Pittsfield’s, have been reclaimed for a new life. Chalk up yet another plus for fall in the Berkshires: the ability to saunter in just about anywhere without a reservation.
I head downtown to Café Adam, a French brasserie that’s earned a reputation as one of the best restaurants in the Berkshires. The small interior is modern, with gorgeous wood floors. The mussels I order as an appetizer are fresh and plump, in a heavenly garlic cream sauce, broken up with the crunch of piquant fennel—and washed down perfectly with a Lost Sailor IPA from local Berkshire Brewing Company. My chicken is, if anything, even more delectable—buttery and juicy under a crackle of skin and accented by a balanced bevy of toppings: sour red onions, golden raisins, and salty collard greens. Just to push the meal over the top, I order a side of decadent truffle fries, accented by a house-made ketchup spiced with a hint of barbecue.
All in all, it’s a meal memorable enough to inspire modern-day Melvilles and Kitsons—all the better for being nearly impossible to come by in summer. As I lean back, contented, thinking back on my weekend—the fiery brilliance of October Mountain, the transformations of the Topia Inn and Canterbury Farm, and two artistic meals in very different settings—I muse that beauty, as well as creativity, comes in many forms.