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The Berkshires | Return to October Mountain

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.


Please Note: This information was accurate at the time of publication. When planning a trip, please confirm details by directly contacting any company or establishment you intend to visit.

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