The Berkshire Mountains in Western Massachusetts have long been a hub for arts and culture, with famous American writers such as Nathaniel Hawthorne, Herman Melville, and Edith Wharton calling this area home. This rich tradition continues today with world-class museums such as the MASS MoCA and the Norman Rockwell Museum; gilded age mansions and homes of famous authors such as Naumkeag and The Mount; and, of course, Tanglewood, the outdoor music center and summer home to the Boston Symphony Orchestra.
But if you are visiting the Berkshires with kids, don’t worry! The Berkshires also have plenty to offer families in terms of year-round outdoor adventure, from skiing in the winter, hiking, ziplining, white water rafting, and treetop adventure parks. It was Tanglewood that first drew us to the Berkshires, but we quickly discovered that there was so much more to do, which is why we love returning to this region to discover something new each time.
Things to do in the Berkshires with Kids
The Berkshires are a year-round destination, with skiing and snow sports in the winter, maple sugar season in the spring, gorgeous foliage in the fall, and world-class museums all year long. I just happen to find the Berkshire extra fun in the summer when visiting with kids.
Listen to Music at Tanglewood
Tanglewood is an outdoor music venue in Stockbridge that has been the summer home of the Boston Symphony Orchestra since 1937. Your kids may not be into seeing the Boston Pops, but I’d encourage you to give it a try as the venue is much more family-friendly! However, Tanglewood is NOT just for the symphony. It also hosts outdoor music festivals and concerts.
My daughter’s first concert was going to see the Indigo Girls (one of my all time favorites) started at the SummerSound Festival at Tanglewood. Before the show, we stopped off at Nejaimes Wine Shop in Lenox to stock up our picnic basket with a selection of cheeses, crackers, prepared foods, and, of course, wine. One of the nicest things about watching the orchestra or another show at Tanglewood is picnicking on the lawn. Everyone sets up blankets, low beach tables, and a spread of food and drink to just relax and enjoy the music and outdoors.
Climb the Trees at Ramblewild
Ramblewild is an aerial adventure park near Jiminy Peak in Lanesborough. Unlike some of the ropes courses that you find at ski resorts, this attraction is recognized as one of the largest, most challenging, and beautiful parks in the country. Built on over 1500 acres of undeveloped forest land, Ramblewild includes an aerial adventure park, a children’s aerial trail, hiking trails, and base lodge with picnic area. Plus, it is located in the trees, keeping it shady and cooler, even on hot summer days.
Ramblewild has eight aerial trails from beginner to expert and they are marked like a ski resort, with color coded levels of difficulty. Everyone needs to start at the beginner trail but after that, it is up to you! Your ticket includes up to four hours of climbing.
I will say that not only was this course the most fun of any that I have tried, it was also the most challenging (at least for me!) While I’m not scared of heights, there were parts that made me nervous and it was definitely a work out. Watch the video for the full scoop. You can see that some members of our family were more excited about this than others.
Slide and Climb at Jiminy Peak
In the winter, Jiminy Peak is southern New England’s largest ski resort, with skiing, snowboarding, multiple lodges, and more. But Jiminy Peak is just as fun to visit in the summer. This four-season resort offers a Mountain Adventure Park with a mountain coaster, alpine slide (my favorite!), Soaring Eagle zip line, and other fun attractions.
And, if you want even more thrills, the Aerial Adventure Park has 74 ropes course challenges for all ability levels. You can even visit during the 13 Nights seasonal haunt for some spooky scares.
Berkshire Museum
Great for kids about 14 and under, the Berkshire Museum offers a little bit of everything for families. Downstairs there is a small aquarium, while the main floor covers local wildlife in its small natural history exhibit. For young kids, the museum offers a hands-on Spark! Lab, but we enjoyed learning about local inventors and entrepreneurs in the Feigenbaum Hall of Innovation.
Revisit Americana at the Norman Rockwell Museum
Kids today probably haven’t encountered the work of Norman Rockwell, but through the Norman Rockwell Museum, which houses a significant collection of his work, along with that of his contemporaries, they will soon learn to appreciate his style of American illustration. I believe Rockwell’s style is quite kid-friendly as it isn’t too abstract to be unrelatable.
The museum houses nearly 1,000 pieces of his work, along with original art materials, his library, furnishings, and an archive of 100,000 items including photos, letters, fan mail, and personal items. Rockwell’s Stockbridge studio, which was moved to the Museum site, is open to the public from May through October. You can reserve tickets online to save money and time.
Climb Monument Mountain
Monument Mountain in Great Barrington is one of the more popular family hikes in the area, so plan to go early. Monument Mountain is the site where Nathaniel Hawthorne and Herman Melville enjoyed a picnic and had a discussion that helped inspire Moby Dick. This mountain offers views all the way west to the Catskills in New York on a clear day. For the easiest hike, start off on the Indian Monument Trail to the left of the parking lot for a 1.51 mile hike toward the summit. The trail guide said we’d pass the remains of Native American trails but we clearly missed those.
To get any view, you need to take the steeper Squaw Peak Trail, but just use caution with kids as there are some steep drop offs. Hannah and I then took the steeper .83 mile Hickey Trail on the way down (better than on the way up!) to complete the loop, while Glenn went back the way we came. Just off the path of the Hickey Trail we found small waterfalls and narrow streams – much prettier than the less scenic hike through the forest on the way up.
We definitely just got a taste for all there is to do in the Berkshires with kids, but what I loved about the area is that it isn’t just outdoorsy or just artsy – you can have something for everyone with shopping, art, music, dining, and plenty of adventure.
Be Wowed at Mass MoCA
Massachusetts Museum of Contemporary Art (also known as Mass MoCA) isn’t your typical art museum. With miles of galleries featuring large scale contemporary art installations, it is sure to capture the interest of your kids.
Beyond the exhibits themselves, Kidspace at MASS MoCA centers on experiential learning and inspiring curiosity in the arts. Families are encouraged to foster self expression and nurture your own creativity in the Kidspace. In addition, there is a hands-on art bar studio and family story times.
Step Back in Time at Hancock Shaker Village
Hancock Shaker Village offers a glimpse into the life and legacy of the Shakers, a religious sect known for their simplicity and craftsmanship. This living history museum isn’t just for adults – families can enjoy a fun-filled day exploring the historic village. Kids can participate in interactive exhibits like learning traditional Shaker crafts, playing period games, and even helping with farm chores.
Families can also embark on a scavenger hunt through the village, uncovering hidden secrets and stories along the way. Don’t miss the working farm with adorable animals, or grab a bite at the on-site cafe. Whether exploring the historic buildings, engaging in hands-on activities, or simply enjoying the scenic grounds, Hancock Shaker Village provides a memorable and educational experience for the whole family. Just keep in mind that Hancock Shaker Village is only open from mid-April through October.
Hit the Rapids with Zoar
Experience the thrills of whitewater rafting with Zoar Outdoor on the Deerfield River. Famed for its consistent flow and exciting rapids, the Deerfield offers a range of rapids, from family-friendly Class II-III to adrenaline-pumping Class IV. Zoar Outdoor provides various tours, including half-day, full-day, and multi-day adventures.
Their most popular trip, the Zoar Gap is ideal for beginners ages seven and up, while the Dryway is more thrilling with class IV rapids for those 14 and older. Zoar also offers zip lining and guided kayaking trips.
Let Your Imagination Run Wild at Naumkeag
Naumkeag was originally the summer estate of prominent lawyer Joseph Choate, built in the late 1800s. Today, this 48-acre site offers a glimpse into the Gilded Age through tours of the grand, shingle-style mansion. But the real star of the show are the stunning gardens, designed by Mabel Choate in collaboration with landscape architect Fletcher Steele.
Families can wander through themed gardens, like the Blue and White Garden or the Chinese Garden, each offering a unique visual and sensory experience. Kids will especially enjoy the whimsical topiary garden, with its playful animal shapes, and the expansive lawns perfect for rolling around or a picnic. Don’t miss the seasonal events, like the winter light show “Naumkeag Winterlights,” which transforms the grounds into a magical wonderland of twinkling lights and festive displays. Naumkeag is open from spring through fall, except for seasonal events.
Visiting Massachusetts? You may also be interested in…
- Winter weekend in the Berkshires
- 9 Things to do in Springfield, MA for the whole family
- Things to do in New England with kids
- Christmas in Massachusetts
- 29 Best museums in New England with kids
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Tamara Gruber is the Founder and Publisher of We3Travel. A former marketing executive and travel advisor, Tamara is an award-winning travel writer and recognized expert in family travel. Tamara is a member of SATW and the Adventure Travel Trade Association, and serves on the Board of the Family Travel Association. She is also the publisher of YourTimetoFly.com and the co-host of the Vacation Mavens travel podcast.
