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Let’s Hit the Family Fun Trail!

Posted on April 27, 2022Written by 1Berkshire Marketing Team
Updated on June 12, 2026

A family poses in front of a colorful block wall at MASS MoCA.MASS MoCA. Credit Aden Seeley.

Ready for family fun and adventure in the sun?

The Berkshires have just what you need, be it activity in the beautiful outdoors or participating in hands-on learning! No matter if you are a visitor or lucky enough to live here, there are plentiful activities to enjoy with family members of all ages.

Whether your Berkshire getaway is for one day or several, Crab Apple Whitewater, at the northern end of the County, is the perfect place to channel some energy during the sun-soaked Berkshire spring and summer months. Spend the day on the scenic Deerfield River, whitewater rafting or river kayaking with qualified guides, or glide through the treetops on a zipline! For longer stays, enjoy onsite lodging in the renovated farmhouse or set up a tent on the expansive campground. You can also make your way to MASS MoCA in North Adams where Kidspace awaits. Tour the colorful exhibits and hands-on activities, including The New Sound of Music, geared to activate children’s imaginations and creativity.

A woman and young child pet a calf

High Lawn Farm

If you happen to be visiting the central Berkshire area, the Magic Wings Butterfly Conservatory and Gardens in South Deerfield are a must-see for everyone in the family! Open year-round, experience over 3,000 colorful butterflies as you stroll through an indoor tropical garden. Don’t be surprised to see one rest on your shoulder! You can stop for a snack and peruse the gift shop as well. Next, be sure to visit the farm animals—and their adorable babies!—at the unique and historic Hancock Shaker Village in Pittsfield. Learn about life as a Shaker on this 750-acre farm, with hands-on activities for the kids in the Schoolhouse and Discovery Barn, where you can milk a life-size replica of a Holstein. No Berkshire visit is complete without a bit of indulgence at Chocolate Springs in Lenox. Adults and kids alike will delight in chocolate creations of all sorts—including baked goods and a signature hot chocolate. Gelato and ice cream are sure to bring a smile.

Nature-loving families can check out all the outdoor recreation opportunities in the Berkshires through BerkshiresOutside.org. It’s a great resource for planning your next outdoor adventure. Search by activity or location to find exactly to family-friendly option for your crew to experience the Berkshires’ natural beauty together. Families visiting Lenox may also want to explore The Mount, where beautifully maintained grounds, seasonal family programming, and outdoor events create an enjoyable experience for visitors of all ages. Nearby, the trails and lakes of Pleasant Valley Wildlife Sanctuary offer opportunities for wildlife observation, easy hikes, and nature-based learning. Don’t forget to stop at High Lawn Farm for some delish ice cream and a visit with the adorable calves! 

Have you been to the Mahaiwe Theater in Great Barrington? Make sure your Family Fun Trail takes you there! The Mahaiwe offers educational and family programming, as well as dance, music, comedy, and drama on its historic stage and screens. Built in 1904, the Mahaiwe offers quality performances in a building that espouses the elegance and beauty of days gone by, a genuine treat for all. After the show, pop into Coco’s Candy for old fashioned sweets. 

Woman hands child an apple on the dock at Pleasant Valley with a fall backdrop

Mass Audubon’s Pleasant Valley Wildlife Sanctuary, credit Great Sky Media

With so much to see and do across the Berkshires, you will certainly find something to engage everyone in the family, no matter age, interest, or budget. Make a plan to explore your own Family Fun Trail and uncover some new and exciting adventures, and make unforgettable memories along the way! Find more ideas for family activities here.

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