Winter Sports in The Berkshires

A person should have wings to carry them where their dreams go, but sometimes a pair of skis makes a good substitute. – Hans Gmoser

With a variety of downhill, cross-country, and backcountry skiing, along with snowshoeing and snow tubing options, plus a host of great lodging and dining choices, and a plethora of lessons and clinics, the Berkshires offers a winter wonderland of choices when it comes to hitting the slopes.

Feeling a little overwhelmed? We’ve got your back!

Berkshire East, a family-owned resort and ski area up north in Charlemont, has teamed up with the centrally-located Bousquet Mountain, and Catamount Mountain Resort in southern Massachusetts, to offer the Berkshire Summit Pass!  Explore the terrain in each Berkshire region, and enjoy the unique qualities of each resort. 

Berkshire East boasts a diverse community of dedicated snow bunnies and eager first-timers who enjoy skiing, mountain biking, and all kinds of winter adventure sports, and is the sister resort of Catamount Mountain Resort. Catamount (which straddles the border of Egremont, Massachusetts and Hillsdale, New York) has a beautiful new lodge, a new lift, and hundreds of new snow-making machines, making it one of the finest small ski areas in the region. With Catamount and Berkshire East, winter delights run in the family!

Bousquet Mountain in Pittsfield is the oldest existing ski area in the Berkshires with a rich history of celebrity patrons like the Kennedys and the Fords, as well as a cozy local vibe. Check out their eclectic programming for kids and adults, as well as their racing leagues and snow tubing lanes! 

While you’re in the central Berkshire area, head on over to Windsor and pay a visit to Notchview. Notchview is part of the Trustees of Reservations who are renowned for their commitment to land conservation, horticulture, and ecological and cultural advocacy. The Notchview ski area is also famous for its 25 miles of pristine shoe showing and cross-country ski trails. A separate trail system is even set up for skiing with your dog (otherwise known as “skijoiring”)! 

If cross country skiing is your jam (and you also enjoy eating jam), you will definitely want to visit Maple Corner Farm. A working family farm in Granville, Maple Corner has 20 kilometers of cross-country trails as well as separate trails for snowshoeing. You won’t want to leave without picking up a jar or two of their famous maple syrup, fruit butters, and yes, jam! A little later in the season their Maple Sugar House is open to visitors interested in watching sap being boiled into syrup (and interested in consuming said syrup on Maple Farm’s delicious pancakes and French toast breakfasts).

Have we piqued your interest in shoe showing and yumminess? You must plan a visit to Hilltop Orchards! Located in Richmond and home of Furnace Brook Winery, Hilltop is the ideal place to snowshoe and hike before enjoying a Covid-safe wine and cider tasting, experiencing a cidery tour, or relaxing with apple cider and donuts.

These days, we all value businesses that are good stewards of the land. With 100% renewable energy from wind turbines, cutting edge technologies, and a resort staff committed to green environmental practices, Jiminy Peak Mountain Resort is the pride of Hancock. Jiminy’s fabulous skiing and snowboarding opportunities, and variety of nearby lodging choices (everything from a country inn to vacation condos) also offer conscientious visitors a ton of fun!

The fun never stops at Ski Butternut, where there is something for everyone. Do you need a “First Timers Package?” Are you interested in “Women’s Wednesday” or the “Christmas Camp” racing program? Ski Butternut, in beautiful Great Barrington, has lots of niche programs to choose from as well as advanced programs for experienced skiers. 

Let the winter games begin! Looking for more winter fun inspiration? Check this out!

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Ski Conditions

Learn more about skiing in the Berkshires and find trail conditions and snow reports.