25 Things To Do in the Berkshires with Kids

Climb Monument Mountain for panoramic views of the Berkshires. Photo courtesy of Massachusetts Office of Travel & Tourism
Climb Monument Mountain for panoramic views of the Berkshires. Photo courtesy of Massachusetts Office of Travel & Tourism
9/26/20 - By Kelley Heyworth

The Berkshires may be associated with romantic escapes and girls' getaways, but make no mistake: This hilly, charming region of western Massachusetts is a great choice for a family getaway. With breathtaking nature trails, waterfalls, mountains, quirky museums, and welcoming farms dotting the region, the Berkshires offer something for all kids, especially ones who appreciate the outdoors and the arts. We've narrowed down our 25 favorite things to do in the Berkshires as a family.

Our New England Travel Guide has more ideas for exploring all the region has to offer, including our favorite nearby state parks and forests for outdoor adventures. 


Tanglewood's Ozawa Hall shines at dusk. Photo by Steve Rosenthal

1. Tanglewood

Every summer, the Boston Symphony Orchestra takes up residence in Lenox, Massachusetts, for Tanglewood performances, and one of the great traditions of the Berkshires is packing up a picnic and enjoying amazing music on the lawn in front of Ozawa Hall.

2. The Bookstore in Lenox

Get some vacation reading in at this beloved Lenox bookshop. With titles for all ages, this cute little shop has an especially great selection of children's classics. Bonus: There's a wine bar next door, which allows you to sip while the kids read.

3. Haven Breakfast

Order morning croissants and a warm drink at Haven, where breakfast is an all-day affair if you want it to be. We're partial to hot chocolate or a cinnamon vanilla latte with a flaky croissant, which they'll make into french toast if you have time to sit.

4. Riding at Aspinwall Adult Equestrian Center

Guides and gentle horses lead riders ages 10 and up on a short or long ride around Kennedy Park and other Lenox trails.

RELATED: The Dr. Seuss Museum and More Fun Things To Do in Springfield, Mass.

Kids will learn about animals and simpler ways of life at Hancock Shaker Village. Photo courtesy of Hancock Shaker Village

5. Hancock Shaker Village

Celebrating the simple design and agricultural advancements of the religious sect that populated the area in the 19th century, Hancock Shaker Village will teach kids about a simpler way of life. Check out the blacksmithing, house building, and dancing demonstrations held daily across the grounds, as well as interactive exhibits that allow visitors to spin wool or milk a cow. 

Meet the lambs at Ioka Valley Farm. Photo by the author

6. Ioka Valley Farm

The highlight of Ioka Valley Farm in Hancock is definitely the friendly barn animals that roam quite freely around the property. During the summer months, you can let kids meander among the sheep, goats, and alpacas, and then play in the farm-themed playground, hay tunnel, and 40-foot slide, or race pedal carts around a track.

Zoom down the Mountain Coaster at Jiminy Peak.  Photo courtesy of Jiminy Peak

7. Jiminy Peak

Spend an afternoon—or a day or even weekend—at Jiminy Peak. Though it's maybe best known as a ski resort, Jiminy Peak has a ton of warm-weather fun, including a mountain adventure park with a ropes course for kids 6 and up, rides (including a mountain coaster and alpine super slide), a bungy trampoline, and, of course, many super hiking trails.

8. Joe's Diner

Cool down with an ice cream float at Joe's Diner. Sipping a creamy, cool drink from a red stool at this old-fashioned diner in Lee is a perfect afternoon treat.

See iconic scenes of American life, courtesy of Norman Rockwell. Photo courtesy of Norman Rockwell Museum

9. Norman Rockwell Museum

Introduce the kids to America's most beloved illustrator at Stockbridge's Norman Rockwell Museum. Home to the artist's most important works, the museum will spark conversations about history and social conventions, but also features cartoons and many tongue-in-cheek drawings that kids will love.

10. Red Lion Inn

 Sit down to a traditional family meal at the Red Lion Inn in Stockbridge. The kid's menu goes beyond finger food to introduce kids to some New England classics, like clam chowder, Vermont cheddar cheese and crackers, and locally sourced prime rib.

The Incredible Naumkeah Pumpkin Show is not to be missed! Photo courtesy of the trustess

11. Naumkeag

This Gilded Age mansion has magnificent gardens that kids will love to scamper through and family-friendly programs throughout the year. Consider a visit during October for the Incredible Naumkeag Pumpkin Show, or December, when the property is bedecked with thousands of holiday lights.

MASS MoCA is a vast massive multi-building museum in the Berkshires in a refurbished old factory site. Photo courtesy of the museum

12. Mass MoCA

People come from far and wide to visit Mass MoCA, a giant modern museum with many interactive exhibits, as well as Kidspace, where families can create their own works of art.

13. Hoosac Valley Train

Train lovers will want to take this scenic ride, which starts in North Adams and winds around the region for an hour before returning to the station. The air-conditioned ride is a great break during warm weather, and the vintage-Christmas-themed rides are special during holiday time.

14. Berkshire Outfitters

This well-known Berkshires gear shop has bicycles for all ages, and staffers can point you in the direction of the paved Ashwillticook Rail Trail, just 300 yards from the shop.

15. Mount Greylock

Reach the highest point in the state by ascending Mount Greylock in the northern Berkshires. To break up the long journey to the 3,491-foot peak, you can make a reservation at the campground or lodge, which are open during the summer, or drive close to the summit. Strong older children can make the full ascent in just a few hours.

RELATED: 100 Fun Things to Do in New England Before Kids Grow Up

A short hike leads to Balance Rock, a boulder balancing in a precarious way! Photo courtesy of Balance Rock State Park

16. Balance Rock

Littler ones' stamina (and attention span) might be better suited for a walk to Balance Rock. A short hike leads to the big draw: a 165-ton boulder balanced naturally, and unbelievably, on a small patch of bedrock.

17. Monument Mountain

If you are looking for a kid-friendly hike with the reward of great views on the end, hit Monument Mountain in Great Barrington. Follow the 1.5-mile Indian Monument trail for a leisurely ascent, or the 0.7-mile Squaw Peak trail for a steep, shorter climb that includes some exciting rock scrambling.

18. Baba Louie's

Great Barrington is full of excellent restaurants and shops. Everyone loves Baba Louie's for the wood-fired pizza and family-friendly vibe. 

19. Tom's Toys

This beloved Berkshires toy store has a selection of some 20,000 playthings, from books to classic games to hot new toys.

20. Berkshire Museum

Spark curiosity at Pittsfield's eclectic Berkshire Museum, which packs a lot of interest into one attraction. There are interactive science exhibits, an aquarium, a giant playroom, and more.

21. Berkshires Carousel

A beautiful reproduction of an antique carousel, this Pittsfield attraction features 39 horses, a donkey, some chariots, and even a spinning tub. 

Dropping 60 feet, Bash Bish Falls is worth the hike to see it. ​Photo by Pablo Sanchez/CC BY 2.0

22. Bash Bish Falls

While it may be too much to navigate the huge network of trails in Mount Washington State Forest, it's worth paying a visit to Bash Bish Falls if you can carve out the time. Truly one of the most stunning waterfalls in the eastern U.S., the falls drop 60 feet into a sparkling pool below.

23. Zip Line tour

Berkshire East and Zoar Outdoor are two popular spots for canopy rides and other outdoor adventures in the eastern Berkshires' town of Charlemont. 

Magic Wings Butterfly Conservatory Garden is a peaceful stop during a Berkshires trip. Photo by BenFrantzDale/CC BY 2.0

24. Magic Wings Butterfly Conservatory Garden

This 8,000-square-foot observatory is filled with beautiful butterflies of all colors, shapes, and sizes. The waterfall, peaceful music, and docile creatures flitting around will definitely add a note of peace and calm to your trip.

25. Appalachian Trail

If you have older kids with some geographical or historical interests, it will be fun to hop on a stretch of the Appalachian Trail. Ninety miles of the trail are in Massachusetts and run smack through the Berkshires. Check out the map here to see where a good trailhead might be, according to your whereabouts and schedule.

A version of this article first published in 2017.