Top Winter Activities in Lenox, Stockbridge and the Berkshires Region
Winter is a beautiful time to visit the Berkshires, whether you’re here for outdoor adventure or a relaxing getaway, winter in the Berkshires offers the perfect mix of snowy scenery, cozy moments, and cultural experiences. The surrounding area is filled with charming local shops and restaurants perfect for warming up after a day in the snow.
Hit the Slopes at Bousquet Mountain or Jiminy Peak Mountain Resort
Skiing and snowboarding are a big part of winter in the Berkshires, and several great mountains are just a short drive from Lenox or Stockbridge. Bousquet Mountain is nearby and perfect for families and beginners, while Jiminy Peak Mountain Resort offers a larger ski experience with night skiing, rentals, and lessons. For more experienced skiers, Catamount Mountain Resort is a great option with longer runs and beautiful views. After a day on the slopes, it’s always nice to come back to Berkshires Untold to warm up, and unwind.
Explore the Outdoors with Snowshoeing and Winter Walks
If you prefer a quieter way to enjoy the season, winter in the Berkshires is perfect for slowing down and spending time outdoors. Snowshoeing or cross-country skiing at Mount Greylock State Reservation offers peaceful trails and stunning winter views. You can also enjoy scenic walks through nearby conservation areas or try winter hiking on well-marked trails. These experiences are a great way to take in the natural beauty of the Berkshires at a relaxed pace.
Warm Up with Arts and Culture Close to Lenox
When the temperatures drop, the Berkshires’ arts and culture scene offers plenty of ways to stay warm. The Clark Art Institute is a favorite for its impressive collection and calm winter atmosphere, while Mass MoCA makes for an easy day trip filled with contemporary art and indoor exploration. Local theaters and music venues also host seasonal performances, adding something special to winter nights in the region. The Norman Rockwell museum is another local favorite as the painter and illustrator of mid-century Americana called the Berkshires home. Ticket packages are available from Berkshires Untold
Cozy Dining and Breweries Near the Berkshire Untold
After a day out in the cold, there’s nothing better than a good meal and a warm drink. Guests at Berkshires Untold are close to a variety of locally owned restaurants serving comforting New England favorites, as well as craft breweries and cideries that are perfect for après-ski drinks. Nearby cafés and bakeries offer cozy spots to grab coffee, hot chocolate, or a sweet treat. The Club Room at Berkshires Untold is recognized as the Berkshires best kept secret cocktail lounge.
Relax and Recharge During Your Winter Stay
Winter is the perfect excuse to slow down and relax. Berkshires Untold offers a comfortable home base where you can unwind after a full day of exploring. Spend a quiet evening reading, planning the next day’s activities, or take advantage of nearby spas and wellness options for a little extra relaxation during your stay.
Winter Events and Seasonal Charm in the Berkshires
The Berkshires stay lively throughout the winter with seasonal events and celebrations. Holiday lights, winter festivals, concerts, and theater performances bring extra charm to the colder months, along with New Year’s events and community gatherings in nearby towns. These moments make winter visits feel festive and memorable.
Make Berkshires Untold Your Winter Home Base
With its convenient location on Pittsfield Road just 2 miles from the village of Lenox, Berkshires Untold is an ideal place to stay while exploring everything winter in the Berkshires has to offer. Whether you’re visiting for skiing, arts and culture, great food, or a quiet weekend away, winter is a peaceful and rewarding time to experience the region.
