Powder laps in the morning and performance art in the afternoon — such is the winter life in Western Massachusetts. The region’s ranging mountains and snow-covered forests create a spectacular backdrop for outdoor recreation such as skiing and snowshoeing while its small towns have long provided respite for artists. In the 19th century, painters, artisans, and writers began retreating from nearby big cities to the Berkshires and surrounding areas to find solitude and the space to create. (Take, for example, Edith Wharton, who needed space so badly she had a 35-room mansion built in Lenox called The Mount.)
Photo: Heidi Besen/Shutterstock
In Western Mass, Après Means Art, Fine Cuisine, and New England Hospitality
In recent decades, an influx of world-class museums and design-centric hotels, bars, and restaurants has only bolstered the region’s artistic pedigree. Alongside this flood of creative energy, the outdoor adventure industry — anchored by the region’s ski areas — has been thriving since the 1930s. While Western Mass makes for a perfect getaway in any season, winter brings lower temps and often substantial snowfall totals, allowing visitors to ski and snowboard the varied on- and off-piste terrain of the Berkshires and Taconic Mountains, then take advantage of the region’s arts, culture, and dining for a well-rounded après experience.
Where to ski (and not ski) in Western Mass
Bousquet Mountain
Photo: Christopher B Adair
One of the oldest ski areas in North America — and past host to the likes of Jackie Kennedy and Gerald Ford — Bousquet Mountain is a deservedly beloved winter sports playground. A 15-minute drive from Pittsfield, Bousquet has 200 skiable acres, a terrain park, several tubing lanes, and night skiing (it was the first ski area in the US to illuminate its slopes for skiers). If you’re looking for lift tickets and nearby accommodation, Ski & Stay Packages make it easy to plan a getaway.
Bousquet Mountain: 101 Dan Fox Dr, Pittsfield, MA 01201
Berkshire East Mountain Resort
Photo: Christopher B Adair
Varied terrain, night skiing, and a laid-back atmosphere welcome skiers and riders willing to venture off the beaten path a bit. Berkshire East’s base area is rustic, festive, and amenity filled, recalling Taos or Steamboat Springs. Rest your legs at Crazy Horse, where burgers, poutine, and beer are served to guests still in their ski boots.
Berkshire East Mountain Resort: 66 Thunder Mountain Rd, Charlemont, MA 01339
Jiminy Peak Mountain Resort
Photo: Christopher B Adair
With a true village at its base — including condos, restaurants, shops, and a market — Jiminy Peak provides a ski-in/ski-out experience, a rarity in the region. At the bottom of Ace of Spades (if you’re willing to brave a black diamond) and John Hancock (if you aren’t), you’ll find John Harvard’s, a quintessential New England pub where you can warm up with a bowl of clam chowder and a fried haddock sandwich. If you want more time on the slopes, at night you can ski under the lights (which are, like the rest of the resort, powered by 100 percent renewable energy).
Jiminy Peak Mountain Resort: 37 Corey Rd, Hancock, MA 01237
MASS MoCA
Photo: Heidi Besen/Shutterstock
No place better embodies Western Mass’ unique blend of industrial roots and artistic spirit than MASS MoCA. A sprawling complex of former factory buildings in North Adams, the museum is home to expansive works of widely varying mediums. At the moment, these include a multi-story exhibit of wall drawings, a 40-foot-tall light installation by James Turrell, and an entire working roller coaster. The campus is also home to several shops and restaurants, such as Casita, a recently renovated Mexican eatery locals raved about.
MASS MoCA: 1040 Mass MoCA Way, North Adams, MA 01247
Where to eat and drink in Western Mass
White Lion Brewing Company
Photo: Christopher B Adair
The first craft brewery in Springfield, White Lion’s community-driven ethos is reflected in its location in the heart of downtown Springfield. While founder Raymond Berry discussed the brewpub’s history, I sampled a selection of its fantastic beers and small bites before being led through the brewing process by head brewer Mike Yates. You’d be remiss not to order the blueberry sour, sticky ribs, and catfish nuggets.
White Lion Brewing Company: 1500 Main St, Springfield, MA 01103
Methuselah Bar and Lounge
Photo: Christopher B Adair
Methuselah’s eclectic food menu and bar program rely heavily on locally sourced produce and Massachusetts-based brewers and distillers. Highlights were the generously appointed charcuterie board and bafflingly delicious Cuban sandwich. From the bar, avail yourself of the Paper Plane (rye whiskey, Aperol, amaro, lemon juice) and solid array of local draft beers.
Methuselah Bar and Lounge: 391 North St, Pittsfield, MA 01201
Dottie’s Coffee Lounge
Photo: Christopher B Adair
At Dottie’s, fresh pastries, hearty brunch favorites, and handcrafted espresso drinks are served in a series of intimate and welcoming gallery-like rooms. Take in the cafe’s abundance of local art with a Berkshire breakfast sandwich and fresh coffee in hand.
Dottie’s Coffee Lounge: 444 North St, Pittsfield, MA 01201
The Barn Kitchen & Bar
Photo: Christopher B Adair
With a name that belies its refined setting and cuisine, The Barn offers farm-to-table fare, exceptional service, and a well-curated wine list. Executive chef Ron Reda and his team are crafting inventive New American dishes marked by fresh, local ingredients. Standouts were the flat iron steak with rosemary frites, The Smoking Gun (bourbon, mezcal, and orgeat syrup), and an ornate scallop amuse-bouche that was itself a work of art.
The Barn Kitchen & Bar: 103 Spring St, Williamstown, MA 01267
Where to stay in Western Mass
We hope you love these hotels! Just so you know, Matador may collect a small commission from the links on this page if you decide to book a stay. Listed prices are accurate as of the time of publication.
Hotel on North
Photo: Christopher B Adair
Drawing on Western Mass’ deep well of creativity, Hotel on North comprises 45 thoughtfully designed, exceedingly spacious rooms. My suite featured a small library, two TVs, and a clawfoot tub (others have fireplaces and kitchenettes). Occupying adjoining historic 19th-century buildings in downtown Pittsfield, the hotel has a gorgeous atrium on the second and third floors, a ground-level boutique, and an exhibit space in the lobby.
Hotel on North: 297 North St, Pittsfield, MA 01201
The Williams Inn
The classic New England inn was given a sophisticated update in 2019 when Williams College reopened its namesake hotel in an elegant new farmhouse-style building across from campus in Williamstown. Rooms at The Williams Inn are outfitted with plush queen- and king-sized beds, high-speed WiFi, and décor that utilizes local materials. You’ll need only traverse an art-filled corridor to get from the hotel’s lobby to its restaurant, The Barn (mentioned above), which should be a welcome break after a day of skiing.
The Williams Inn: 101 Spring St, Williamstown, MA 01267
How to get to and around Western Mass
Photo: The Global Guy/Shutterstock
I used Peter Pan Bus Lines to get from New York City to Springfield, Massachusetts. The buses were roomy and comfortable, and the service was extremely punctual — something that was remarked on by multiple people in our group. Visitors coming from outside of the Northeast can fly into Albany, New York, then take a train to Pittsfield. Depending on your itinerary, you may need to rent a car, as rideshare options can be limited in certain areas. 