Berkshires Whiteout


Making the most of winter in Western Massachusetts

The swath of the Appalachian Mountains that runs north to south in western Massachusetts has served as an idyllic playground for weekenders from Boston and New York City for more than a century. The Berkshire Hills, as they’re called here, roll lazily southward from Mount Greylock, at the northern end, down through the towns of Pittsfield, Lenox and Great Barrington. It’s no wonder the business tycoons of the Gilded Age chose this area, with its hilltop views, to build grand summer cottages. But while those houses and the region’s many other weekend residences are geared toward summer use, visitors have started to take advantage of all that the area has to offer in winter, from snowshoeing and cross-country skiing to skating on frozen ponds.

BY SKI OR SHOE

The region’s gentle slopes might not provide the face-numbing downhill thrills found in nearby Vermont or New Hampshire, but there’s a surprising number of places to lay tracks on fresh powder. The most notable downhill skiing is at Jiminy Peak, in Hancock, where 9 lifts and 45 trails (including a handful of glade and mogul runs) cover a rather large chunk of mountain. After a morning on the slopes, take a ride on the Mountain Coaster, a 3,600-foot-long raised track through the snowy woods. Strapped into a seated, single-person sled, you can control your own speed, topping out around 25 mph. Finish the day with twilight skiing or wind down with a beer and burger at John Harvard’s Restaurant & Brewery.

Families will find easier runs—and an expansive kid’s program and ski school—at Butternut Basin, just east of Great Barrington. Gradual inclines and plenty of cruising trails provide soft cushioning for beginners; sign the kids up for a half- or full-day group lesson before taking off on your own leisurely run.

KID-APPROVED ADVENTURE

Across the heart of this bumpy range, high-elevation forests flatten into long meandering stretches where you’ll find family-run outdoor activity centers, including Canterbury Farm, which offers an alternative to the nearby corporate resorts. Up a gravelly road in Becket, Canterbury sprawls across 176 acres, with 12 miles of cross-country ski and snowshoe trails. Owners Linda and Dave Bacon run the wooded trails (hiking is popular in warmer months) as well as a B&B in a 220-year-old farmhouse. Their trail fee is $15 per day; for an additional $15, you can take a moonlight snowshoe tour. A pond at the foot of a hill behind the house serves as an ice skating rink, where they also offer lessons.

Several miles west of Lenox, right on the New York border, Hilltop Orchards is open during the growing season for tours of its winery and cider orchard. In winter, visitors come to glide along the cross-country ski trails or take guided moonlight snowshoe tours, heading out just after dusk for an exhilarating two-hour trek. Snowshoers return to the warmth of the winery for cider and tunes played by a duo of acoustic guitarists by the fireplace. (The tours take place only when the moon is full, so call ahead for details.)

If the winds are howling, you can still connect with nature in the small, state-of-the-art Hopkins Observatory at Williams College, in Williamstown. The country’s oldest observatory, it presents nighttime shows all winter. Get there earlier in the afternoon to visit the neighboring Williams College Museum of Art, where you’ll find rotating exhibitions of contemporary art, before the Observatory’s evening show.

 

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