Winter Fun for Families in the Berkshires

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The Berkshires are a beautiful and historic Massachusetts region known for its stunning scenery and outdoor activities. If you’re looking for family-friendly things to do in Massachusetts, there are many amazing family-friendly things to do in the winter in the Berkshires!

From sledding and skiing to exploring world-class museums, there’s something for everyone.

What Do with Kids in the Berkshires in the Winter

I probably don’t have to tell you that winter in New England can be challenging. Bad weather or freezing temperatures make it hard to get excited about going outside to do something, but in the Berkshires, it’s easier than in many places.

With outdoor activities like skiing, tubing, sledding, and ice fishing, there are a lot of outdoorsy people to do in the winter in the Berkshires with kids.

If you’re not a family who enjoys being outside in the cold, there are also plenty of indoor activities. The Berkshires is home to several great museums and other indoor activities.

Here are just some of the fun things to do with kids in the Berkshires this winter.

1) Spend the Day at Jiminy Peak Mountain Resort

Get up early and enjoy the day or a weekend at Jiminy Peak. There is no shortage of winter fun at this popular Berkshire mountain resort in Hancock.

The whole family can take ski lessons, zip down the mountain on the alpine coaster, play games and make s’mores at the Fire & FunZone, take a scenic chairlift ride, and so much more.

2) Go Snow Tubing Down a Mountain

What is more fun in the winter than riding down a great hill in a sled? Take it even further by tubing down the mountain. Several mountain resorts in the Berkshires offer tubing in addition to skiing and other winter activities.

Tubing is the perfect option if you’re looking for a fun way to spend a winter day. There’s no need to worry about being an expert skier or rider – the hills are perfect for riders of all ages.

One of the Berkshires’ several ski areas is the perfect destination for adventurous families who love the outdoors.

3) Visit The Clark Art Institute

Unlike some art museums, The Clark Art Institute has families in mind. First of all, admission for kids and young adults to the age of 21 are admitted free.

The museum makes discovering art fun for kids with their Looking Carefully cards that encourage children to think about what they see in the art and see it from a new perspective. Sketch pads are also available upon admission so children (and adults) can try to draw like the masters featured on the museum’s walls.

On nice days go for a hike or do some geocaching on their trails. There is a lot of fun to be had for families and kids of all ages.

Norman Rockwell Museum studio, Stockbridge, MA
Photo Credit: Todd Van Hoosear via

4) Explore The Norman Rockwell Museum

The Norman Rockwell Museum, located in beautiful Stockbridge, is home to his paintings, sculptures, and photographs. The museum is a fun and educational experience for families to discover.

Kids can enjoy the different exhibits with an audio tour geared just for them. In addition to the artwork, kids can explore the 36 acres of grounds outside. They can follow the paths and explore the fields and gardens. The museum store even sells sidewalk chalk, balls, jump ropes, and more that can be used outside.

Whether you’re looking for a fun day trip or a weekend getaway, the Norman Rockwell Museum is a great place to take your family.

5) Enjoy Outdoor Winter Sports

Being the most mountainous part of Massachusetts, the Berkshires are known for their winter sports. You can go skiing, ice skating, sledding, tubing, ice fishing, and snowshoeing all over the region.

Some of our favorites are:


The Berkshires are home to several mountains for skiing. Whether you’re an advanced skier or a beginner, there is a hill for every skill level. Lessons are also available at many ski resorts in the area.

Ice Skating

In addition to some ponds that are safe for skating, the Berkshires has several ice skating rinks that don’t require a membership.


Snowshoeing is another popular winter activity in the Berkshires. With many trails to follow, you will never get bored or run out of places to explore.

6) Ride Down the Best Sledding Hills

While there are plenty of mountains in the Berkshires, you might just want to grab a sled and go to a sledding hill. We have you covered there, too. These hills are favorites of the locals and are worth the trip.

7) Check Out the Animals at the Berkshire Museum

The Berkshire Museum in Pittsfield is home to a variety of exhibits and collections. There is something for everyone at the Berkshire Museum, from live animals, dioramas, history, science, and art.

Some especially kid-friendly highlights include The Berkshire Museum Aquarium, Animals of the World in Miniature, Berkshire Backyard, and The Rocks and Minerals Gallery.

The museum also hosts special events and programs for kids throughout the year, so be sure to check their events calendar before planning your visit.

Photo Credit: Massachusetts Office of Travel & Tourism via

8) Tour a Gilded Age Mansion

Ventfort Hall in Lenox is a fun place to explore and imagine what life was like for the rich and famous in the late 19th Century. This restored Gilded Age mansion turned museum was built in 1893 for Sarah Morgan, who was the sister of J. P. Morgan.

Ventfort Hall is one of 75 “cottages” built in Lenox, which was a popular area for socialites and high society to build homes. It attracted the rich as well as authors and artists such Nathaniel Hawthorne, Herman Melville, Henry Wadsworth Longfellow, and others because of its gorgeous lake and mountain views.

9) Tour The Mount Estate

Another breathtaking turn-of-the-century estate to tour is The Mount, which was home to author Edith Wharton. The 16,850 square foot mansion currently sits on 49.5 acres of preserved woodlands and is something to experience. They don’t build houses like this anymore!

The mansion has gorgeous gardens that are a must-see in the warm months, but the house is also an awe-inspiring place to visit when you want to get out of the cold while visiting the Berkshires in the winter.

Final Thoughts

The Berkshires offer a variety of activities and attractions for families to enjoy all year, even during the winter months.

Whether you’re looking for outdoor adventure or indoor exploration, you’ll find it all here. So head to the Berkshires for winter fun that your family will never forget!

Featured Photo Credit: Massachusetts Office of Travel & Tourism

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