How to Enjoy a Skiing Escape to Western Massachusetts

The Berkshires of Western Massachusetts are a superb skiing destination, with slopes available for all experience levels—especially beginner and intermediate—and within reasonable driving distance of Boston, New York and Hartford. A host of excellent lodgings and several top-notch restaurants add to the region’s wintertime allure.

Instructions

Difficulty: Easy

Things You’ll Need:

• Warm clothing

1. Consider making your lodgings in Lenox or Stockbridge, two of the area’s more charming towns. If your budget allows, consider staying at Blantyre or Canyon Ranch, both in the Lenox area; Blantyre is an incredible Tudor mansion showcasing elegant accommodations and dining, and Canyon Ranch is no less impressive—and home to one of New England’s finest spas.
2. For something a bit more affordable, and decidedly offbeat, give the all-inclusive Eastover Resort a try, also in Lenox. This one-time ‘singles’ escape now caters to family and corporate getaways as well, offers plenty of activities (including low-key skiing) and has a casual nightlife element as well at its Tally Ho club (although you should be forewarned that Eastover is a BYOB establishment).
3. About a 30-minute drive northwest from Lenox you’ll find the Jiminy Peak Mountain Resort, a skiers paradise that also extends lots of lodging, decent dining, a country store, and lively tavern.
4. Other skiing options in the area include Butternut Basin in Great Barrington, a nice family choice; Bousquet Ski Area, in Pittsfield; and the large Berkshire East in Charlemont, with 45 trails and even a ‘tubing park’ that both kids and adults will like.
5. For an evening of innovative entertainment, take in an arty film or creative live performance at the ’62 Center for Theatre and Dance in Williamstown. Three venues offer plenty of choices, and after a day of skiing it can be nice to take a break from it all by getting off your feet.
6. One of the best dining options in the region is undoubtedly Great Barrington’s Castle Street Café, with delicious delicacies that range from appetizers like Maryland Crab Cakes and Fried Shrimp Dumplings to main courses such as Filet of Salmon Saffron Sauce and Grilled Cornish Game Hen. The Church Street Café in Lenox is also a solid choice, but unfortunately closes for several months beginning in late December.
7. For a night out of libations and socializing, drop by the Zinc Bar at Bistro Zinc (another reputable dining spot as well) in Lenox. A hip and comfortable atmosphere, good wine selection and creative cocktail list make it a prime spot to hang out on a cold winter night.

Tips & Warnings

• Make reservations well in advance for popular lodgings such as Blantyre and Canyon Ranch.
• Check road and weather conditions before driving to Western Mass in the winter.