In Western Mass, Après Means Art, Fine Cuisine, and New England Hospitality

26.02.2024 - 20:03 / matadornetwork.com / Jackie Kennedy / Art

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.)

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.

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

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

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