How to get there
The most picturesque route for the three-hour-or-so drive up to Western Massachusetts is via the Taconic Parkway, which slices through the eastern edge of New York before you turn and head just across state lines into the Berkshires. The prettiest pitstop en route is Milan, the anchor of horse country here; have lunch at Cider Bros. Roadhouse, owned by an alum of the CIA in Hyde Park nearby, known for upscale comfort food. Or, book a riding lesson; Hidden Hollow Farm is a non-profit here that offers them to people with and without disabilities.
What to do
Though the area might be fairly famous for its superb leaf-peeping each fall, it’s arguably even better once the snow starts and the hills morph into some of the best ski slopes in Massachusetts. Take the huge range of terrain at Catamount, ideal for families of varying abilities; there’s also a two-hour zipline tour that includes the adrenalin-pumping CataMonster line, an unbroken, 1,000-foot drop. Butternut Basin is another family-friendly, must-ski hub that offers private family lessons for kids ages four and up, while there are 45 different runs at Jiminy Peak in the Taconic Mountains. Otherwise, there are 13 miles of cross-country ski trails at Canterbury Farm, as well as the chance to skate safely, outdoors, on Farm Pond.
Where to stay
The newest of the ultra-luxe wellness retreats, Miraval (from $1,198 per night) just opened its third property near Lenox: the sprawling campus is anchored by an enormous spa, of course, but the food is another lure: the all-inclusive rates allow you to graze its mindful eating menu on a whim, whether made-to-order smoothies at breakfast, or roasted heirloom carrots and pie made from local apples at suppertime. A quirkier option nearby is 33 Main, an eight-room inn owned and operated by homeware designer Annie Selke, who grew up nearby. Cannily, she intended it to be as much showroom as hotel—most elements of each room are available for purchase to take home with you.