New England Deep Cuts: Pittsfield

The mountain city of Massachusetts

Every once in awhile, MIND THE MOSS bucks the format of highlighting one unusual New England hike—swapping out the standard lens for a telephoto and highlighting a region where you can not only go for a great hike but combine a hike with savory grub, historic curiosities, emerging art, and more. This sub-series, “New England Deep Cuts” has included spotlights on locales like Vermont’s Northeast Kingdom or the Great North Woods of New Hampshire (beyond the White Mountains!) But this year, we’re going even deeper and burrowing into cities that offer primo access to the elements of a decadent hiker’s weekend. And to kick off things off, this year’s inaugural New England Deep Cut is about Pittsfield, Massachusetts. A little city in the mountains.

Downtown Pittsfield MA (@downtownpittsfield) • Instagram photo

What makes a mountain city different from a mountain town? First, size matters. With over 43,000 residents (at the time of the most recent census) Pittsfield is the largest town in the Berkshires and the governmental center of Berkshire County. By contrast, North Adams’ population clocks in below 12,000. Then there’s the walkability and the layout of Pittsfield. The main artery of the city center—North Street—is a classic urban boulevard with department store buildings, theaters, parklets, and restaurants whose doors are often exuding seductive aromas. The grid-shaped side streets are rustling with cosmopolitan temptations, you can catch an Amtrak train to the city, and buses operated by the Berkshire Regional Transit Authority make it possible to not only hop around downtown but to explore Pittsfield’s more wooded and suburban haunches.

I know this because my first brief visit to Pittsfield was in 2019, when I was writing a story for Boston Magazine about what it was like to go from the Berkshires to Cape Cod using only public transportation. (The short answer: a beautiful pain in the ass.) I had a three hour layover in Pittsfield and it began with taking shelter from a monsoon in Dottie’s Coffee Lounge, an irresistible little cafe where the menu features intrepid offerings like a literal cinnamon toast crunch latte and the “Barbershop Sandwich,” an inexplicably delicious Ménage à Trois of bacon, eggs, and peanut butter. From there, I trekked over to Rose & Cole’s Transportation Co-op, which helps residents without cars close the “last miles” of trips that not covered by public transit routes. I hadn’t even been in Pittsfield for an hour and yet, my first impression reminded me of the feeling I got when reporting airline magazine stories from overlooked cities like St. Louis, Cleveland, and Jacksonville. This is a place where you can build cool things.

Like many smaller American cities, Pittsfield’s earlier growth and development is the ripple effect of manufacturing. Until the early 2000s, General Electric was one of the city’s biggest employers. The downsizing and closure of these facilities across the U.S. landscape can have both a devastating and galvanizing effect on cities. The economic consequences are stark and sometimes cities don’t come back from them. But in the shadows of shuttered plants, civic pride can endure and creativity can take root and yield wonders. And in Pittsfield, you can witness this creativity manifesting in pretty much all of the arenas that constitute a great New England hiking weekend.

Let’s start with the hikes themselves. You’re never far from the forest in Pittsfield. You can literally see the mountains beckoning nearby as you walk down North Street. (For a killer urban view of Mount Greylock, zip into the Holiday Inn and take the elevator to the 12th floor.) On the northwest side of the city, the Pittsfield State Forest is an 11,000-acre treasure trove of hikes like the 2.9-mile Lulu Brook Trail, which visits a high altitude spring, or the tougher 5.4-mile Shaker Trail. This one takes you through the ruins of the old Hancock Shaker Village religious site, while also reaching the summit of Shaker Mountain (elevation: 1,845 feet.) Even closer to the city center, The Boulders is one of many rustic conservation lands managed by the Berkshire Natural Resources Council (BNRC). The trails begin next to a Taco Bell. Within minutes, you’re spirited away into a realm of ferns, mosses, glacial erratics, and gusty city overlooks.

But the creative side of Pittsfield really starts to show when you consider the city’s options for long cross-country hikes. This is a rare corner of America where you can experience the European-style “walking holiday”—in which one hikes from one town to the next, refueling in restaurants and resting at local inns. Mindy Miraglia, a Pittsfield resident, offers guided hiking tours of the Berkshires and its towns. These adventures can range from day hikes to multi-night journeys, and the routes can be customized. Miraglia’s business, Berkshire Camino, was inspired by multiple treks along Spain’s iconic “long walk.” Funnily enough, the Camino de Santiago was also the inspiration behind a massive, emerging project from the BNRC. The council has been hard at work building and blazing The High Road, an epic trail that will run south to north along the spine of the Berkshires, passing through Pittsfield and the neighboring towns. The first segment of The High Road, which opened in 2021, ambles from Pittsfield’s Bousquet Mountain ski area to the Kripalu campus in Lenox along the Yokun Ridge, traversing Mass Audubon’s Pleasant Valley Wildlife Sanctuary along the way. It’s a glorious and refreshingly gentle sun-splashed trail that involves prolonged immersion in deciduous forests. I’ve hiked it twice: once for a Lonely Planet story and again with my dad during peak foliage season. For a 10-mile hike, it’s an ecstatic trip.

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Both the Berkshire Camino trips and the High Road utilize either pre-existing forest paths and dirt roads to create unique hiking experiences. It’s an example of how “trail-building” can involve taking overlooked or forgotten elements and clicking them into something dazzling. And when you’ve had your fill of hiking around Pittsfield, you’ll find that this model of place-making spills over to the city’s culinary and hospitality circuits. For a downtown base camp, consider the Hotel on North, a former men’s department store that’s been re-imagined as a boutique hotel with Grand Budapest-like touches such as library nooks and decorative harpoons and tennis rackets on the walls. (The “posters” for your four-poster bed could be preserved support beams.) If you’d prefer a woodsier ambiance, try the Yankee Inn on the south side of town. From the bustle of Rt. 7, this cozy budget hotel looks like any other, but the facade hides a lovely “backyard” where you can sit in Adirondack chairs beside a beaver pond and watch the sun set behind Yokun Ridge. Or you can just watch the beavers, like I did.

Of course, half the point of any hike is giving yourself a license to inhale something gooey and crumbly. And Pittsfield offers more menus than you could possibly hope to peruse over one weekend. You could immerse yourself in the twinkling lights at Methuselah Bar & Lounge and try cocktails with gingery portobella mushroom tacos. You can burrow into the soft-lit dive bar scenery of Thistle & Mirth and discover that the place also offers a seriously umami-rich bowl of ramen. If you’re like me, you could grab pizza with friends and not have to worry about disagreements over what kind of cheese or house-made toppings you choose, thanks to the dizzying menu of customize-able thin-crust pies at the appropriately named CRUST. (It’s a fine crust.)

Whatever you do, one place you really need to scope out—when it opens in the very near future—is Hot Plate Brewing. This downtown-situated brewery was born in the apartment of its two founders, who found themselves without heat or hot water due to a code violation by the building owner and till managed to brew their first beers using a single hot plate in lieu of a stove. Hot Plate appears to be subverting the Ron Swanson vibe that a lot of breweries lean into, declining to participate in the hops race and offering inviting gateway beers like a chamomile-infused golden ale. It’s also one of the very few Latina-owned breweries in the U.S. (less than 3% of all breweries!) and each beer has its own origin story and even an accompanying playlist. When meeting Sarah Real and Mike Dell’Aquila, the co-founders, we somehow went from talking about lactose sugars to comparing Weezer’s earliest albums to their more contemporary offerings. It reminded me of the early 2010s, when the craft beer scene felt weirder, shaggier, and when the beers themselves were the subject of theoretical monologues. I’ve tired of the scene lately, but Hot Plate is rekindling my curiosity.

History tends to rhyme, and if you also find yourself moved by the creative echoes of Pittsfield, from the trails to the core of the mountain city itself, I highly recommend concluding your visit with Arrowhead: the home of Herman Melville. Tucked in the hills on the city’s south side, Arrowhead is where Melville cranked out the manuscript for Moby Dick, which was initially panned upon its release before being re-discovered, re-evaluated, and embraced after Melville’s death. For this, we have to thank Melville’s granddaughter, Eleanor, who found Melville’s forgotten manuscript of Billy Budd in a bread tin and got it published, to thunderous acclaim. From the porch of Arrowhead and from the window by Melville’s writing desk, you can see the vast profile of Mount Greylock, which resembles the shape of a whale. Sort of. Given that Melville spent his youth toiling aboard a whaling ship—back-breaking, gruesome work—I’d imagine that he saw whales in many places. (In a generous serving of mashed potatoes, perhaps.)

But standing in his quarters at Arrowhead, guided around the sanctuary by author and writer-in-residence Jana Laiz—you can arrange a tour of Arrowhead a week or more in advance of your visit—I couldn’t help but be humbled the scale of the mountains and the immensity of the creative labor and heartbreak that characterized Melville’s life. In the end, his imagination and his immeasurable efforts changed lives and the face of American literature as we know it. Many of us won’t live to see the ripple effects of our own creative endeavors. But in Pittsfield, whether you’re disappearing into the mountains or gazing at those same mountains from North Street, you can witness, experience, and savor the outcomes of a more collective creativity. A civic impulse.

A mountain city of the highest order.

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