Planning a family trip can feel overwhelming. I’ve been there searching for a place that keeps kids happy and gives adults something to enjoy too.
The Berkshires in Western Massachusetts checks every box. In this guide, I’ll walk you through the best things to do in the Berkshires for families from outdoor activities and art museums to great food spots and cozy places to stay.
I’ve put this list together with real families in mind. You’ll also find tips on when to go and where to book.
Why Families Love Visiting the Berkshires?
The Berkshires is a small but packed region in Western Massachusetts. It’s easy to get around, and most spots are within a short drive of each other.
Families keep coming back for a few simple reasons. There’s a strong mix of outdoor fun and cultural spots. Kids can hike in the morning and visit a hands-on museum in the afternoon. The area works well for both summer vacations and fall foliage trips.
Summer brings festivals, swimming, and outdoor concerts. Fall brings some of the most colorful leaf-peeping in New England. Either way, you won’t run out of things to do.
19 Best Things to Do in the Berkshires
A complete guide to the best family-friendly activities, dining spots, and places to stay in the Berkshires, Western Massachusetts.
1. Ride the Alpine Slide at Jiminy Peak Mountain Resort
Jiminy Peak isn’t just a ski resort. In the warmer months, it becomes a full outdoor activity park for families. Kids can ride the mountain coaster, tackle the ropes course, or zip down zip lines.
The alpine slide is a crowd favorite. You control your own speed, which makes it fun for both nervous younger kids and thrill-seeking older ones. It’s a great way to spend a few hours outdoors without overthinking it.
2. Bike the Ashuwillticook Rail Trail
This 11-mile trail runs through the Hoosic River valley, and it’s completely flat. That makes it a solid choice for families with younger kids or casual riders.
The trail passes through Cheshire and Adams, with views of the river and wetlands along the way. You can rent bikes nearby if you don’t bring your own. Pack snacks, take your time, and enjoy the fresh air.
3. Visit the Norman Rockwell Museum
Norman Rockwell’s work tells simple, honest stories about everyday American life. His paintings feel familiar even if you’ve never studied art.
The museum in Stockbridge has a great interactive art room where kids can draw and create. Older family members will appreciate the full collection of original paintings and illustrations. It’s one of those rare spots where every age group leaves with something to talk about.
4. Wander the Gardens at Naumkeag
Naumkeag is a historic estate in Stockbridge with layered gardens, open lawns, and seasonal family programming. The terraced gardens are well-kept and fun to walk through, even with small children.
There’s enough open space for kids to run around. The seasonal events including a popular light show in late fall give families a reason to visit more than once.
5. Visit Massachusetts Museum of Contemporary Art (MASS MoCA)
MASS MoCA is one of the largest contemporary art museums in the country. It sits in a former factory complex in North Adams, and the scale of it alone is worth seeing.
The KidSpace exhibits are made specifically for younger visitors. Large-scale art installations fill multiple buildings. Even if your kids aren’t art lovers, the size and creativity of the space tends to win them over.
6. Tour Hancock Shaker Village
This living history museum gives families a real look at how the Shakers lived and worked. There are farm animals, hands-on craft demonstrations, and 20 original Shaker buildings to walk through.
Kids often love animals the most. Adults tend to appreciate the craftsmanship and the calm of the space. It’s the kind of place that sneaks up on you when you go in curious and leave genuinely impressed.
7. Hike at Mount Greylock State Reservation
Mount Greylock is the highest point in Massachusetts. There are trails for all skill levels, including shorter, easier paths that work well for families with young children.
At the top, you get wide-open views across several states on a clear day. There’s also a war memorial tower and a lodge. Bring layers, it can get cool even in summer.
8. Attend a Concert at Tanglewood
Tanglewood is the summer home of the Boston Symphony Orchestra. It’s set on a large, open property in Lenox, and lawn tickets are very affordable.
Families spread out blankets, set up picnics, and listen to live music under the sky. Kids don’t need to love classical music to have a good time here. The atmosphere is relaxed and welcoming.
9. Visit The Mount
The Mount was the home of novelist Edith Wharton. The house tours give a window into early 20th-century life and design, and the gardens are well worth walking through.
It’s a good stop for older kids and teens who are curious about history or literature. Younger children will enjoy the grounds. The setting is peaceful and the views of the surrounding landscape are lovely.
10. Paddle or Swim at Onota Lake
Onota Lake in Pittsfield is a go-to spot for families who want a slower day. You can rent kayaks or paddleboards, swim in the designated areas, or simply sit by the water.
It’s low-cost and low-key, which makes it a great option after a busy stretch of sightseeing. Pack a lunch, bring sunscreen, and plan to stay longer than you think you will.
11. Stroll Downtown Great Barrington
Great Barrington has a walkable downtown that feels genuinely lived-in. There are independent bookstores, local shops, cafés, and several good restaurants within a few blocks of each other.
It’s a good base for a relaxed afternoon. Kids can browse while adults grab coffee. The energy is calm and the people are friendly.
12. Visit Lenox Village
Lenox is a small, walkable village with boutiques, galleries, and easy access to Tanglewood and The Mount. It’s a comfortable place to spend an afternoon between bigger activities.
The streets are quiet and the pace is slow, which families often appreciate. There are a few good ice cream shops nearby, always a bonus when traveling with kids.
13. Visit North Adams’ Arts Scene
North Adams has a creative, arts-forward energy that’s different from the rest of the Berkshires. Murals cover building walls throughout downtown. Small galleries and studios sit alongside local coffee shops and restaurants.
Walking through North Adams feels like an open-air gallery. Kids often respond well to the large-scale murals. It’s a great complement to a visit to MASS MoCA nearby.
14. Indulge at Chocolate Springs
Chocolate Springs in Lenox is a small artisan chocolate shop that kids absolutely love. The handmade truffles, toffees, and confections are made in-house.
It’s a quick stop, but a memorable one. Pick up a small box to share or let each family member choose their own treats. The prices are reasonable for the quality.
15. Dine at Great Barrington Brew Pub
This laid-back pub in Great Barrington serves solid burgers, sandwiches, and casual American fare. The setting is relaxed and the portions are generous.
It’s a good option for families who want a no-fuss dinner after a long day of activities. The staff is friendly, and the atmosphere is easy-going without being loud or chaotic.
16. Stop at Pedrin’s Dairy Bar
Pedrin’s is a classic drive-in in Westfield, just outside the Berkshires, but worth the mention for families passing through. They serve burgers, fried clams, onion rings, and thick milkshakes.
It’s the kind of old-school food stop that kids remember for years. The food is simple and good. Lines can get long on weekends, so plan accordingly.
17. Eat at PUBLIC eat + drink
PUBLIC eat + drink in North Adams is a casual spot with a rotating seasonal menu. Think soups, tacos, flatbreads, and sandwiches made with local ingredients.
The space is relaxed and welcoming. Families with picky eaters will appreciate the variety on the menu. It’s a solid choice for lunch or an early dinner after visiting MASS MoCA.
18. Stay at The Red Lion Inn
The Red Lion Inn in Stockbridge is a historic landmark that’s been welcoming guests since 1773. It has comfortable, well-appointed rooms and a warm, old-fashioned feel.
Families enjoy the central location in Stockbridge, which puts them close to the Norman Rockwell Museum and Naumkeag. The dining room and wraparound porch are popular spots to wind down in the evening.
19. Book a Suite at The Porches Inn
The Porches Inn in North Adams is a colorful boutique hotel made up of renovated Victorian row houses. Rooms are spacious and well-designed, with a fun, creative energy that fits the North Adams arts scene.
It’s directly across from MASS MoCA, which makes it a convenient base if you’re spending time in that part of the Berkshires. The pool and common spaces are a hit with kids.
Tips for Planning Your Family Trip
A little planning goes a long way when visiting the Berkshires with kids.
- The best time to visit is summer (June through August) and fall (September through October). Summer offers the most activities and events, while fall draws visitors for the leaf color, which typically peaks in mid-October.
- Staying somewhere in the middle of the region like Lenox or Pittsfield keeps driving distances short, no matter which direction you head.
- Fall foliage weekends fill up fast. If you’re visiting in October, reserve accommodations and restaurant tables at least a month in advance.
- Even in summer, Berkshire’s mornings can be cool, especially at higher elevations. Bring layers for hikes and evening concerts.
- A full week of museums can wear kids out just as much as a full week of hiking. Alternating between outdoor and indoor activities keeps everyone’s energy balanced.
Conclusion
The Berkshires surprised me the first time I visited. I expected a quiet weekend and ended up with a full week’s worth of things to do. It hit every note for our family.
From hiking at Mount Greylock to grabbing chocolates in Lenox, there was always something worth doing. I hope this list helps you plan a trip your family will actually enjoy.
If you found this helpful, share it with someone else planning a visit. And drop a comment below with your favorite Berkshires spot. I’d love to hear what worked for your family.
Frequently Asked Questions
What is the best time of year to visit the Berkshires with kids?
Summer and fall are the most popular times for families. Summer offers outdoor concerts, swimming, and full access to activity parks, while fall brings colorful foliage across the region.
How many days do you need in the Berkshires?
Most families enjoy a stay of three to five days. That gives you enough time to cover a mix of outdoor activities, museums, and local dining without feeling rushed.
Are the Berkshires good for young children?
Yes. Many attractions, including the Ashuwillticook Rail Trail, Onota Lake, and Hancock Shaker Village, are well-suited for younger kids. Indoor options like MASS MoCA and the Norman Rockwell Museum also have family-focused areas.
Is the Berkshires expensive for families?
It depends on your choices. Some activities like hiking and biking trails are free or low-cost. Lodging and dining can run higher in peak season, so booking early and choosing casual restaurants helps manage costs.
How far is the Berkshires from Boston and New York City?
The Berkshires is roughly 2.5 hours from Boston and about 2.5 to 3 hours from New York City, making it a practical weekend or short-week destination from either city.
