young person enjoying winter in the Berkshires

When the air turns cold and the snow begins to fall, choose the Berkshires of Massachusetts for your winter escape.

The Berkshires are known for being a cultural haven during the warm months of the year. Art and music enthusiasts flock to Western Massachusetts for the chance to experience some of the great performances held at world-renowned locations such as Tanglewood & Jacob’s Pillow. This can sometimes make it difficult for last minute reservations at area B&Bs, such as The Inn at Stockbridge, during the summer months. Fortunately, there are plenty of reasons to come and enjoy a Berkshires winter as well.

Top Reasons to Experience A Berkshires Winter

Cultural Activities

There are many museums to explore in the Berkshires, including the Norman Rockwell Museum, The Mount, Berkshire Botanical Gardens, and Massachusetts Museum of Contemporary Art. Not only are these museums open for walk-through tours, but they also offer an abundance of classes and workshops. Take a painting or drawing class at the Norman Rockwell Museum or participate in a variety of workshops at the Education Center of the Berkshire Botanical Gardens. If you are interested in health and wellness for the mind, body, and soul, consider joining a program at Kripula Center for Yoga & Health. The best part about all of these enriching cultural activities is that they are right in Stockbridge, so you’re never too far away when you stay at our Inn.

Skiing, Snowboarding, & Tubing

Snowboarding in the Berkshires
Snowboarding & skiing in the Berkshires are awesome.

There is perhaps nothing better in the winter than strapping your boots into some skis or a snowboard or hopping onto a tube and soaring down a mountain. When the snow starts flying, the Berkshires are a great place to enjoy these winter sports and with so many mountains to choose from, you’re sure to find the perfect one. Whether enjoyed at Bousquet Ski Area, Ski Butternut, Jiminy Peak Mountain Resort, or Berkshire East Mountain Resort, when you plan a winter vacation in the Berkshires, choosing The Inn at Stockbridge as your basecamp is a no-brainer. We’ll have hot coffee and cocoa waiting for you upon your return after a day of hitting the slopes.

Winter Events

Winter in the Berkshires begins with holiday celebrations in November and carries on through the entire winter season.

Visit the Berkshire Museum in the evening for the Festival of Trees After Dark, hosted every Saturday beginning in Mid-November to just before Christmas. Walk through the indoor forest of creatively decorated trees ablaze with light and listen to the musical motifs that accompany each tree. For a fun challenge, guess the song title that matches each tree’s décor.

Meet Santa Claus at Stockbridge Main Street at Christmas
Meet Santa Claus during the Stockbridge Main Street at Christmas event.

When you stay in Stockbridge, you become a part of its history. Made famous by a Norman Rockwell painting, Stockbridge Main Street at Christmas has become a beloved annual event held on the first weekend of December. Stockbridge transforms into a holiday wonderland, with caroling, holiday readings, tours of homes from the gilded age, and a visit from Santa Claus himself. This otherwise quiet village street becomes a busy winter festival ground where Rockwell’s painting is recreated, including vintage cars parked along the streets. This special winter event will quickly become your favorite holiday tradition.

Visit Pittsfield in February for 10 days celebrating the arts. Multiple venues throughout downtown Pittsfield offer fun workshops, showcases, short performances, and more during the 10×10 Upstreet Arts Festival. Experience a variety of arts from painters, actors, musicians, and chefs.

Shakespeare & Company

The Berkshires are rich in culture. That’s a fact. Even in the cold months of winter, communities of the Berkshires can still enjoy performances by great talents. Shakespeare & Company, a global sensation celebrating the work of William Shakespeare, performs a show in December, as well as hosts the Winter Studio Festival of Plays in January. This festival showcases many works of Shakespeare in short plays put on by the Company members. It is a great chance to learn more about the variety of Shakespearean plays, creating an opportunity for educators, directors, and cultural enthusiasts alike to come together during the performance off-season. If there is only one thing you do this winter in the Berkshires, make it this!

Snowshoeing & Cross-Country Skiing

Enjoy the warmth of the fire
Enjoy the warmth of the fire at Hilltop Orchards or right here at our inn!

Snow-covered fields. Perfectly groomed trails. Après ski wine tastings by a roaring fire. You won’t find these things just anywhere. Snowshoeing and cross-country skiing in the Berkshires are enjoyable winter activities for all. Each location that you choose to traverse the snow-covered land offers a little something different. If you’re looking for a leisurely glide in a favorite local spot, Kennedy Park in Lenox offers beautiful flat grounds for Nordic skiing and snowshoeing. The Hilltop Orchards offers up the orchard trails to snowshoers and skiers during the winter months. They also do wine sampling in their indoor lodge next to a blazing fireplace so you can warm up afterward! Some other great locations in the Berkshires to enjoy these winter activities are Notchview, Maple Corner Farm, and Laurel Hill Association.

No matter how you choose to spend your winter vacation, the Berkshire Mountains have something fun to offer visitors of all ages. Whether you are here for winter sports, educational guided tours and classes at the museums, or want to get involved in all the fun winter festivities happening, The Inn at Stockbridge is your ultimate winter lodging basecamp. Add our Warmth & Wellness package to your stay for an extra special winter escape. Retreat here for a Berkshires winter to remember, we’ll be waiting for you!