Winter in the Berkshires: Skiing, snowshoeing, breweries and more

Canterbury Farm's winter activities include cross-country skiing, snowshoeing and ice skating on a frozen pond.
Canterbury Farm’s winter activities include cross-country skiing, snowshoeing and ice skating on a frozen pond. Photo Credit: The Andy Warhol Foundation for the Visual Arts, Inc.

The Berkshires in Western Massachusetts are a patchwork of quaint villages, gentle mountains and rural landscapes. The inspired scenery and peaceful rhythms have long been a magnet for artists, musicians and writers. The area is a favorite retreat for urbanites who crave nature but don’t want to skimp on culture. If you’re seeking a winter getaway with plenty of fresh-air recreational options, the Berkshires are a fine place to invigorate the body and refresh the soul.

Active options

For downhill skiers and snowboarders, Ski Butternut (380 State Rd., Great Barrington, 413-528-2000, skibutternut.com) offers terrain to suit all levels. If you get tired of the slopes, there’s a snow tubing center.

Canterbury Farm’s (1986 Fred Snow Rd., Becket, 413-623-0100, canterbury-farms.com) groomed trails meander alongside brooks and snowy meadows, painting a fairy-tale picture. Cross-country skiing, snowshoeing and ice skating on the frozen pond present a trifecta of frosty fun.  

Local culture

Artisan crafts are thriving in the Berkshires. Brookside Quiltworks (closed Mondays; 2 Sheffield Rd., Egremont, 413-528-0445, brooksidequiltworks.com) sells handmade quilts and offers instructional workshops.

The area’s rich agricultural heritage is on display at Cricket Creek Farm (1255 Oblong Rd., Williamstown, 413-458-5888, cricketcreekfarm.com). This sustainable dairy farm welcomes visitors year-round. Stop by the store, which operates on the honor system, for its award-winning farmstead cheeses.

If you’re a fiend for caffeine, you’ll want to dabble in the robust local coffee culture. Learn the secrets of the roasting process during a 90-minute cupping class at Barrington Coffee Roasting Company ($75; 165 Quarry Hill Rd., Lee, 413-243-3008, barringtoncoffee.com).  

Eat and drink

For Italian food, Trattoria Rustica (dinner only, closed Tuesdays; 27 McKay St., Pittsfield, 413-499-1192, trattoria-rustica.com) is perfetto, from the pastas to the veal alla Siciliana. Chef-owner Davide Manzo bakes his own bread daily in the brick oven.  

The restaurant at the venerable Red Lion Inn (30 Main St., Stockbridge, 413-298-5545, redlioninn.com) serves traditional Yankee classics, such as roast turkey with all the trimmings. Don’t miss the warm brown sugar cake, drizzled with caramel sauce and topped with a dollop of ice cream, for dessert.

Big Elm Brewing (open Thursdays-Sundays; 65 Silver St., Sheffield, 413-229-2348, bigelmbeer.com) offers a thirst-quenching lineup of ales and lagers in the taproom, including the popular Fat Boy.


Getting there: The Berkshires are under a three-hour drive from midtown. Buses from Port Authority go to several towns, including Sheffield, Great Barrington and Lenox (peterpanbus.com).

Getting around: Public transportation within the region is limited so a car is a good bet.

Where to stay: Wheatleigh (11 Hawthorne Rd., Lenox, 413-637-0610, wheatleigh.com) is a 19-room hotel that was originally a private estate with rambling grounds designed by Frederick Law Olmsted. Antique furniture, exquisite stained glass windows and museum-quality artwork make it an aristocratic immersion. Gateways Inn (51 Walker St., Lenox, 413-637-2532, gatewaysinn.com) is a homey bed-and-breakfast. In a nod to the area’s literary legacy, each of the 11 guest rooms is named after a Shakespearean heroine.