The Berkshires, a picturesque region in western Massachusetts, transforms into a winter wonderland when snow blankets its rolling hills and charming towns. From outdoor adventures to cozy indoor experiences, the area offers many activities for visitors and locals alike. Explore 30 fun and festive winter activities that make the Berkshires a perfect cold-weather destination.

The Berkshires in winter offer an ideal blend of outdoor adventures and cultural experiences. Snow-covered landscapes provide a backdrop for skiing, snowshoeing, and sledding, while the region’s rich cultural heritage shines through its museums, theaters, and historic sites.

For outdoor enthusiasts, the options are plentiful. Ski resorts like Jiminy Peak and Butternut cater to downhill skiing and snowboarding fans, while cross-country skiers find paradise at Notchview.

Ski at Jiminy Peak. Carve up the slopes at the largest ski resort in southern New England. Jiminy Peak boasts 45 trails and nine lifts, catering to skiers and snowboarders of all skill levels.
Go snowshoeing at Pleasant Valley Wildlife Sanctuary. Strap on snowshoes and explore seven miles of trails winding through forests and meadows. The sanctuary’s pristine winter landscape offers a peaceful escape into nature.
Take a horse-drawn sleigh ride. Snuggle under warm blankets as you glide through snow-covered fields on a traditional horse-drawn sleigh. Several farms in the area offer this magical experience.
Visit the Norman Rockwell Museum. Immerse yourself in the iconic artist’s depictions of American life. The museum houses the world’s most extensive collection of Rockwell’s original artwork.
Enjoy a spa day at Canyon Ranch. Pamper yourself with luxurious treatments at this world-renowned wellness resort. The heated indoor pool provides a perfect retreat from the winter chill.

Cross-country ski at Notchview. Glide through 3,000 acres of forests and fields on 25 miles of groomed trails. Notchview offers some of the best Nordic skiing in Massachusetts.
Attend a concert at Tanglewood. While primarily known for its summer music festival, Tanglewood hosts winter concerts in its intimate Linde Center for Music and Learning.
Go ice fishing on Onota Lake, a scenic lake in Pittsfield. Local outfitters can provide equipment and guidance for beginners.
Visit MASS MoCA. Explore contemporary art in a sprawling complex of renovated 19th-century factory buildings. MASS MoCA is one of the largest centers for contemporary visual art in the United States.
Snowmobile through the October Mountain State Forest. Rev up your engine and cruise through 16,500 acres of winter wilderness. The forest offers designated trails for snowmobiling enthusiasts.

Take a cooking class at The Chef’s Shop in Great Barrington and learn new culinary skills in a cozy kitchen setting. The Chef’s Shop offers courses ranging from bread-making to international cuisines.
Go tubing at Butternut. Experience the thrill of sliding down snowy slopes without the need for skiing skills. Butternut’s tubing center provides family-friendly fun for all ages.
Attend the Pittsfield Winterfest. Join the community in celebrating winter with ice sculptures, hot chocolate contests, and live entertainment during this annual February event.
Visit Hancock Shaker Village. Step back in time at this living history museum. Winter programs offer insights into Shaker life and crafts during the colder months.
Enjoy a wine tasting at Furnace Brook Winery. Warm up with a selection of locally produced wines. The winery at Hilltop Orchards offers tastings and beautiful winter views.

Ice skating at the Boys & Girls Club of the Berkshires. Lace up your skates and glide across the ice at this indoor rink in Pittsfield. Public skating sessions are available throughout the winter.
Hike Monument Mountain. For the adventurous, a winter hike up Monument Mountain offers stunning views of the snow-covered Berkshire landscape. Remember to wear appropriate gear and check trail conditions.
Attend a performance at the Mahaiwe Performing Arts Center. Enjoy live theater, music, and dance performances in this beautifully restored theater in Great Barrington.
Visit Ventfort Hall Mansion and the Gilded Age Museum. Explore this Jacobean Revival-style mansion that is decorated for the holidays. Learn about life in the Gilded Age through exhibits and guided tours.
Go stargazing at Bartholomew’s Cobble. This National Natural Landmark offers excellent stargazing opportunities on clear winter nights away from city lights.

Take a pottery class at IS183 Art School. Get creative and warm up your hands by molding clay into unique pieces. IS183 offers various art classes throughout the winter.
Enjoy afternoon tea at The Mount. Indulge in a traditional afternoon tea service at Edith Wharton’s historic home. The elegant setting provides a perfect respite from winter’s chill.
Visit the Berkshire Museum. Discover a diverse collection of art, history, and natural science exhibits. The museum’s aquarium is a particular favorite among younger visitors.
Go dog sledding with Hilltown Sleddogs. Experience the thrill of mushing through snowy trails led by a team of energetic sled dogs. It’s an unforgettable winter adventure.
Attend a chocolate-making workshop at Chocolate Springs. Learn the art of chocolate-making from master chocolatier Joshua Needleman. Indulge your sweet tooth while gaining new skills.

Visit the Animagic Museum of Animation. Explore the world of special effects and animation at this unique museum in Lee. It’s a fun and educational experience for all ages.
Enjoy a winter hike at Mount Greylock, Massachusetts’ highest peak, which offers breathtaking views. The roads to the summit close in winter, but hiking trails remain open for experienced winter hikers.
Attend a glass-blowing demonstration at Schantz Galleries. Watch skilled artisans create stunning glass pieces. The gallery also showcases beautiful contemporary glass art.
Take a winter wildlife tracking workshop. Learn to identify animal tracks and signs in the snow. Several local nature centers offer these educational and fun outdoor programs.
Cozy up with a book at The Bookstore & Get Lit Wine Bar. Browse a wide selection of books, then settle in with your choice and a glass of wine at this charming bookstore and wine bar in Lenox.

Snowshoeing at Pleasant Valley Wildlife Sanctuary or hiking Monument Mountain offers a quieter way to enjoy the winter scenery. For a unique experience, try dog sledding or take a romantic horse-drawn sleigh ride through the snow. Indoor activities provide a cozy counterpoint to winter’s chill.

The region’s world-class museums, including the Norman Rockwell Museum and MASS MoCA, offer artistic inspiration and cultural enrichment. Music lovers can enjoy winter concerts at Tanglewood or performances at the Mahaiwe Performing Arts Center.

To taste history, visit Hancock Shaker Village or tour the Gilded Age splendor of Ventfort Hall. Culinary experiences abound in the Berkshires. Take a cooking class, enjoy a wine tasting, or indulge in a chocolate-making workshop. The region’s farm-to-table restaurants showcase local ingredients even in the depths of winter.

For families, activities like tubing at Butternut, ice skating, or visiting the Berkshire Museum provide fun for all ages. The Pittsfield Winterfest brings the community together to celebrate the season with ice sculptures and festivities.