Planning the Perfect Berkshires Winter Getaway

Winter in the Berkshires is beyond picturesque—during this time of year, this region of western Massachusetts becomes a snowy wonderland. Winter sports enthusiasts come from near and far to experience the playground of towering trees, snow-covered mountains, and boutique inns and cabins, providing a perfect blend of cultural experiences against a backdrop of winter's peaceful beauty. Here’s how you could spend your winter trip to the Berkshires this year. 

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Skiing and Snowboarding

When it comes to winter activities in the Berkshires, skiing and snowboarding reign supreme. Grab your boots and skis (or board!) and head to Jiminy Peak Mountain Resort for a great Berkshires skiing and snowboarding experience. With over 45 trails across 167 acres, you’re bound to spend the whole day on the slopes. Also a plus: the resort sources 100% of its electrical energy from renewable resources. Whether you’re a first chair warrior or only there for the aprés ski, you’ll soon see why skiing in the Berkshires is a must on our list of winter activities in the area.

Hiking 

It’s no secret that winter hiking offers its own unique opportunities and challenges. Glistening trees tower beside you, the trail beneath your feet is snowy and wet, and the view from the peak is peaceful, quiet, and painted in white. This is winter beauty at its finest—what’s not to love? If we’re speaking your language, opt for Cascade Trail in North Adams. Classified as “easy,” this 2.2-mile round trip crosses the brook on a bridge, involves climbing up rocks, features waterfalls, and is known to be a lovely winter wonderland walk through the woods.

Bay State Winter Games 

Feeling competitive? This annual competition consists of an array of winter sports, including figure skating, ice hockey, futsal, ice skating, and curling. The athletes range in age from five years old to over 70 and represent numerous different communities across the states of Massachusetts, Maine, New Hampshire, Vermont, and Rhode Island. Since 1982, this non-profit organization has worked to promote personal development, education, teamwork, and more around New England. 

Visit The Red Lion Inn This Winter

There are so many things to do in the winter near Stockbridge! After an exciting day of exploring, stay at The Red Lion Inn. Cozy and comfortable, we’re just a short walk or drive away from all the best winter adventures. Ready to get away? Book your room now

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