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The Berkshires | Return to October Mountain

The Berkshires | Return to October Mountain
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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.

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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