Thanks to plenty of art galleries and theater troupes, plus what may be the nation's highest number of prep schools per capita, the Berkshires aren't often accused of being wild. But these old highlands have secrets, and they're best found in winter. Base yourself in Charlemont, at the Warfield House Inn (doubles from $112; warfieldhouseinn.com), a farmhouse set on 530 acres and overlooking Mohawk Trail State Forest. Rent snowshoes or cross-country skis in nearby Adams, at Berkshire Outfitters (from $25 per day; berkshireoutfitters.com), and get trail info from the Appalachian Mountain Club (amcberkshire.org). Then explore Mount Greylock State Reservation's 70 miles of trails, including the Appalachian. For a workout with a payoff, skin 90 minutes up Greylock on the Thunderbolt Trail, a ski-racing route built in the thirties, then come down in a hurry. (Bring your own alpine-touring setup or rent downhill skis at Ski Fanatics, in Lanesborough, 413-443-3023, and snowshoe up.) Day two: Head 20 minutes to North Adams for some sculpture browsing at the excellent Massachusetts Museum of Contemporary Art ($15; massmoca.org). Hey, it's the Berkshires! NEAREST AIRPORT: Albany, 90 minutes, or Boston, three hours.