PITTSFIELD — For nearly all of the late aughts, I had spent every other winter weekend at Nonna’s house in Pittsfield. Nonna was my friend Eric’s maternal grandmother, but I knew her by no other name. If you’d asked me in 2008 how to spend a weekend in Pittsfield, I’d have suggested Friday-night lasagna at Nonna’s, or a warm bowl of Saturday morning tortellini soup before a ski session at Jiminy Peak, a few towns over.
Eric and I had tried some Pittsfield restaurants in the years that George W. Bush served out his second term. And we’d stood around an empty bar once or twice when Twitter had launched and was less controversial. There wasn’t much happening in town. At least Nonna had aged boxed wine next to the cleaning supplies under her kitchen sink, and one glass got her reminiscing about the Italian countryside and her early days in Pittsfield, when the town was a thriving commercial center.
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But when General Electric shut down its operations in the 1980s, thousands of residents went unemployed, and Pittsfield fell into the pits, leaving North Street a collection of vacant storefronts.
After Nonna died, I stopped visiting Pittsfield. But very recently, I’d heard that the city was experiencing a rebirth and drove in to see it for myself.
A few minutes south of downtown Pittsfield, but within city limits, I clipped into my bindings at Bousquet Mountain. While much smaller than Hancock’s Jiminy Peak, the green-level trails and accessible blue slopes were perfect for my kids, who were still pizza-wedging their way to the bottom. But beginners aside, Bousquet has produced five Olympic skiers.
In recent years, the ski resort had nearly shut down operations for good. But a local investment company, Mill Town Capital, had swooped in to purchase and save Bousquet — as well as a number of historic buildings in town — breathing new life into Pittsfield’s backyard ski mountain. The snow-making is excellent and the brand new base lodge is sleek, with a downstairs food hall teeming with local kids and families, and an upscale, upstairs area with a bright, spacious bar and restaurant. The second-story outdoor deck offers gorgeous views of the mountain. On tap are excellent local beers; on the walls hang enlarged black-and-white photographs documenting Bousquet’s history; and in the air circulates an ambiance that most ski resort eateries do not possess.
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But since downtown is less than a 10-minute drive, skiers can take a break at any number of delicious eateries in the city. Dottie’s Coffee Lounge offers delicious pastries, tasty breakfast sandwiches, and strong coffee. Its Domingo Brunch is a Sunday filled with food and live music from 10 a.m. to noon.
The District Kitchen & Bar on West Street pours hoppy local beers, fine wines, and seasonal cocktails. The cuisine is a cross between grub and gastronomy. Even though it classifies itself as modern American cuisine, Pittsfield’s Italian population probably keeps the pressure on the District to put out solid pasta, which they do. Mushroom and spinach linguine features a few fungi and a truffle cream sauce that does the District proud. For a more traditional Italian meal that Nonna would approve of, walk around the corner to McKay Street, where Trattoria Rustica’s Pompeiian chef does a wondrous eggplant melanzane and prepares seafood as if it came straight from the Tyrrhenian Sea. The décor delivers warmth and something old-world Italian.
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Newly opened is downtown’s first brewery in a decade: Hot Plate Brewing Co. It all started when two Brooklyn-based homebrewers tired of their New York City situation — inspectors had shut off their condominium’s gas in 2017, the gym where they took hot showers for three years shuttered during COVID, and getting wort to boil on electric hot plates had just become too much. So the brewers moved to Pittsfield to open Hot Plate Brewing Co., which crafts some delicious beers, like an Egyptian-chamomile blonde named after a Ben Folds’ song, jalapeno pale ales, and Wu-Tang inspired cream ales. While they’re brewing these days with updated technology, the famed hot plate that had won them homebrew awards in yesteryears is on display in the crisp-looking taproom.
Pittsfield has always been familiar to adjacent-culture. Nearby Berkshire towns have Tanglewood, Mass MoCA, and the Norman Rockwell Museum. But now this Western Massachusetts city has its own art scene. Bousquet hosts music events in warmer months, as does the Hancock Shaker Village, which features the Back Porch Music series that fills the historic property with the sounds of banjoes and bluegrass. Theatrical performances take place at the Barrington Stage Theater Company and the Colonial Theater, the latter of which also offers live music. In February, Pittsfield puts on the 10x10 Upstreet Arts Festival, where 10 is the magic number. Theaters host 10 10-minute plays, museums run 10 days of performances, and other establishments invite comedians and musicians onstage to perform 10-minute sets. Pittsfield’s First Fridays Artswalk — a free, public, often monthly event that will start back up in May — connects businesses and gallery spaces, where local artists showcase their work.
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One of the best gallery spaces in the city is inside the lobby at the Hotel on North. Each of the 45 guest rooms, many of which have lovely claw-foot tubs and unique furniture pieces that were refurbished by the hotel’s in-house engineer, also feature stunning local artwork. The building itself, which was once the Besse Clarke department store, is an architectural gem in the city. Many of its 19th-century elements are well preserved, like exposed brick walls, tin ceilings, and decorative columns. As an ode to the Besse Clarke sporting goods section once housed on the second floor, the hotel has old Louisville Slugger bats and antique tennis rackets as decorations, (as well as reading nooks and sofas). Each guest room has a different layout and varied features — some with kitchenettes, others with gas fireplaces. Most impressive is a corner suite on the third floor. A bed up against a brick wall faces two walls of floor-to-ceiling library shelves, where a rolling ladder can give access to books on every subject from hobbies to Herman Melville. Inspired by the view of nearby Mount Greylock, Melville wrote “Moby-Dick” in Pittsfield. Visitors can tour his Arrowhead home year-round, and in the middle of summer, partake in a multi-day “Moby-Dick” read-a-thon.
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If you walk down North Street and cruise around Pittsfield, you’ll notice that the city has not been scrubbed of all its grittiness. But street art brings balance between Pittsfield’s past and future. The city’s Artscape Paintbox program, which turns unappealing utility boxes into canvases for local artists, is just one way that Pittsfield is digging itself out, painting over the problems of the past, giving the Berkshires another town worth visiting.
Noah Lederman is the author of A World Erased: A Grandson’s Search for His Family’s Holocaust Secrets.