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Ski The Berkshires

Posted on December 04, 2019Written by Lindsey Schmid
Updated on December 04, 2019

Jimmy Peak, Winter skiing

The Berkshires are known for year-round fun, and the winter season never disappoints. As the temperature drops and the snow flies, it’s the time of year we all get our skis, snowboards, and snowshoes out of closet, and get ready to head outside.

Looking for family skiing and outdoor fun? Bousquet Ski Area in Pittsfield has it all, including downhill skiing, boarding, and tubing. Look for special deals on Thursday evenings, or sign up for a lesson with the whole family! They also offer a Tiny Tots weekend program and both midweek and weekend programs for children six and older. Here you will find 24 trails along with three lifts, and if you are looking to warm up, come inside to the Tamarack Lounge for a delicious bite to eat, a cocktail, and maybe some live music! Bousquet also has great wedding options and event spaces often reserved for ski birthday parties.

Speaking of fun skiing getaways, Jiminy Peak Mountain Resort in Hancock is the largest ski/snowboard resort in southern New England. They boast 45 trails, nine lifts, and night skiing. Jiminy also has a nationally-recognized children’s ski program, lessons for the whole family and for those with adaptive needs, and winter break ski camps for kids. If you want to stay on site, the resort offers a variety of options, from a hotel and condominiums at the base of the mountain to standalone houses for rent (some of which are for sale!). When you’re ready to warm up, stop into either of their delicious restaurants for food and merriment. A year-round meeting, event, and wedding destination, Jiminy Peak also has four event spaces with full catering options.

In the Southern Berkshires, there are two great options: Ski Butternut and Catamount Mountain Resort. Catamount, located in South Egremont, enjoy 39 trails, three terrain parks, and eight lifts, including three Wonder Carpet surface lifts. They also offer lessons for the whole family, including those with adaptive needs. If you’re looking for a place to stay, check out available lodging deals with local inns, hotels, and motels. Day or season passes and rentals are also available. Ski Butternut, located in Great Barrington, offers skiing, riding, and snow tubing. This family-friendly mountain has 22 trails and two terrain parks. Lessons are available for the whole family, including multi-week programs and rental/lesson/lift packages. There are also multiple racing programs for kids! Why not make a weekend of it, and ski one on Saturday and the other on Sunday?

Not too far from the Berkshires, you will find Berkshire East Mountain Resort. This ski area is an old-school gem with modern facilities, a great snowmaking system, and first-class grooming, all operated by awesome people! Berkshire East is the only ski area in the world to produce 100% of its electricity from on-site renewable energy. The resort is also home to 38 trails and five lifts, along with a tubing park. A variety of lesson packages are available, as are daily and multi-day rentals.

If going downhill just isn’t your thing, the Berkshires also offers a host of beautifully-groomed cross-country skiing and snowshoeing trails, including Canterbury Farm in beautiful Becket, Hilltop Orchards & Furnace Brook Winery in Richmond (equipment rentals available), gorgeous Notchview in Windsor (cafe and equipment rentals available) and Maple Corner Farm in nearby Granville.

So bundle up, gather your family and friends, and head out for some bluebird days of skiing in the Berkshire snow!

Darcie Sosa is a Berkshire marketing/PR professional, who when isn’t working loves being outside hiking with her dogs, going to live music and theatre shows, networking, trying new restaurants and volunteering for local nonprofits. She is an alum of Berkshire Community College, Massachusetts College of Liberal Arts, and the University of Massachusetts, Amherst.

Photos courtesy (top to bottom):

-Jiminy Peak Mountain Resort
-Catamount Mountain Resort
-Darcie Sosa



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