When we talk about travel in Massachusetts, all of the attention goes to Boston and Cape Cod. But you would be remiss if you didn’t consider a visit to the Berkshires, since it is easily the most beautiful part of the state. Personally, the fall is my favorite time to visit. The crisp mountain air is perfect for hiking and the foliage is beautiful.
There is so much to do in the Berkshires! Many activities that you wouldn’t think would be appropriate for kids are actually quite family-friendly. I was pretty terrified of my kids running through a gilded age mansion, but they were welcomed with open arms. We had such an amazing time that we kept extending our trip. In the end, we spent four action packed days completing the list below.
Here is our ultimate list of what to do in the Berkshires organized by town. This route starts at the southern part of the state and works it’s way north.
Driving route through the Berkshires
Hike to Bash Bish Waterfall
A short scenic hike will take you to the tallest waterfall in the state of Massachusetts. It is important to note that there are two entrances. Since the park is right on the state line, you can enter from Massachusetts (shorter, but steeper) or from the New York side (longer but more gradual). I would recommend the New York entrance. The dramatic 60 foot drop of the waterfalls is just beautiful.
The Berkshires is dotted with gilded age mansions that were owned by wealthy New Yorkers who traveled out to their country “cottages” in the summer. This 44 room house is now owned by the Trustees of the Reservation.
We walked through the house, but real treasure is the gardens. My kids loved exploring the manicured rows of trees and the magnificent mountain view speckled with cows in the distance.
We hadn’t originally planned on visiting here, but it is right across the street from Naumkeag. I was so glad we stopped because it was pretty amazing. There is a large children’s area with a play house, chicken coop and fairy garden. Special crafts and activities take place in the outdoor classroom. I had a hard time dragging them out of there.
Across the street, we walked the trail through various garden areas. It was different from other botanical gardens that don’t want you to step foot off the trail. My kids climbed trees, made forts and found shady secret areas. I loved that we were encouraged to really experience and enjoy the grounds.
By this time, we were ready for lunch. We picked up sandwiches from the deli in the center of town and had a picnic at Turn Park Art Space. The galleries are currently closed due to covid, but the sculpture park is open with a suggested donation. After lunch, we realized that there was a whole area of the park we almost missed. There was a stone amphitheater for outdoor performances, “the eyeball” which became a fort and even outdoor twister.
If you need a pick me up, head down the street to Depot 6 which is known for the best coffee in town.
Norman Rockwell lived in downtown Stockbridge because he thought that it represented the best of America. It was pretty insane to stand in front of an original Normal Rockwell worth $26 million dollars. Or to see the studio that he rode his bike to each day to create what would one day be masterpieces that told the American story. It is inspiring for children to see what hard work and imagination can do.
I worried that the museum would not appreciate having children there and when a docent quietly walked over to us, I thought for sure we would be getting scolded, but she just wanted to tell my kids a story. I thought that was pretty cool.
Hike up to Laura’s Tower
The Ice Glen Trail is up there with my favorite hikes in New England. Stone steps will lead you up and down a winding path leading out to what looks like Ferngully. Follow the trail up to Laura’s Tower for an amazing view over the Berkshires.
The trail is not very well marked, so use an app such as Alltrails to help lead your way. Note that there are two entrances for this hike. We drove down Ice Glen Road to a small parking area on the left and followed the signs from there. Be sure to bring the bug spray. Leashed dogs are welcome.
We stumbled upon this vista in West Stockbridge and the view is pretty spectacular, especially in the fall. It’s definitely worth a stop.
Have a historic stay at the Red Lion Inn
The Red Lion Inn is one of the original New England inns that has welcomed famous visitors such as Nathaniel Hawthorne and Henry Longfellow. Enjoy fine dining on the front porch and take a dip in the slate swimming pool. To read all about our stay at this grand old hotel, click here.
The River Walk follows the west bank of the Housatonic River between Cottage Street and Bridge Street. We only spent about 20 minutes here, but we enjoyed learning about Great Barrington native W.E.B. Du Bois, who was an early founder of the Civil Rights Movement. His love for the Housatonic inspired him to become a champion of rivers around the world.
Rescue the Housatonic and clean it as we have never in all the years thought before of cleaning it… restore its ancient beauty; making it the center of a town, of a valley, and perhaps-who knows? of a new measure of civilized life.
–W.E.B. Du Bois, 1930
Shopping on Main Street
The downtown area of Great Barrington is a great place to stroll and shop. There are several wonderful toy shops. Tom’s Toys was their favorite. I loved Matrushka Toys for their fabulous book collection. The Gifted Child was also a fun place to peruse (note: they have a second location in Lennox). Get your sugar fix at Robin’s Candy Store.
We had planned to eat at Baba Louis which is a local favorite pizza haunt, but it was closed during our visit. We meandered down a pretty alleyway decorated with colorful street art and stumbled upon the Barrington Courtyard. This multi-restaurant outdoor dining experience is such a great idea. You can order from several local restaurants in one place all while listening to live music. From Morrocan to Mexican, there is something for everyone.
Voted the best ice cream in Massachusetts, the Soco Creamery serves up all natural hand-crafted scoops that shouldn’t be missed. I had espresso cookie and it was heavenly. Located on Railroad Street, this section of the road is closed to most traffic so that the kids could safely run around and even listen to live music. I felt like I had found my happy place.
Here is our funny story about The Mount. We arrived and were instantly marveling at how nice the house was when a woman came over and kindly pointed out that we were at the horse stables. We still laugh about it.
To get to the house, you have to walk the winding driveway through the woods. And if you are impressed by the horse stables, just wait until you reach Edith Wharton’s actual home. Edith Wharton was a very famous author during a time that women were only expected to find a proper man to marry. We walked through the house and the kids were completely intrigued by the ghost stories.
Don’t miss having tea on the veranda before meandering through the the perfectly manicured gardens.
Set amidst more than 1,000 lush acres in the Berkshires, Pleasant Valley’s varied trails wind through forests, meadows, wetlands, and along the slopes of Lenox Mountain, making this site an excellent location for easy-to-strenuous hiking. Open every day, 9 am-4 pm
Prior to Covid, 350,000 people visited this sprawling property to lay on a blanket, sip wine and listen to good music. It’s currently closed due to state regulations, but keep it on your radar.
I have never tasted chocolate like this before! These European-style chocolates are almost too pretty to eat. I had a salted caramel truffle and quickly went back in for two more. My kids loved the chocolate dipped marshmallows.
This living history museum was another favorite stop. The Shakers were an intriguing religious group that got their name from the trembling, whirling, and shaking they engaged in during ecstatic worship services. Led by a woman, the shakers came from England seeking religious freedom.
Their original group of eight grew to 300 at the Hancock Shaker Village. Shakers believed that “work was worship” and spent their days living off the land and creating beautiful things, which is why they are most well known for their fine furniture. The kids loved visiting the animals in the round barn. Advanced tickets are not required here since it is such a sprawling property, crowding has never been an issue.
Arrowhead, also known as the Herman Melville House, is a historic house museum in Pittsfield, Massachusetts. Melville was inspired by the beauty of the Berkshires. Moby Dick was published in 1851 and was considered a failure at the time. It wasn’t until the 20th century that it was established as a great American novel.
You can take a guided tour of the home from 10-3. Tours are on the hour and last about an hour. The museum is open Thursday through Monday (closed Tuesday and Wednesday).
I’m going to admit, I am not a big art person. But even I was blown away by this contemporary art museum. The Mass Moca is what put North Adams on the map. It is a seemingly endless complex of rooms in a rehabbed industrial building.
There are always unique and interesting things to look at. Children will love Kidspace where they can use all that new inspiration to create something of their own. The singing bridge is also fun to run through.
Natural bridge state park
Natural Bridge State Park is home to the only natural white marble arch in North America. It is pretty amazing to see what a melting glacier can do to bedrock over 550 million years. You can walk down precarious looking pathways to get an up-close look at the rock formations.
There is also a birch lined meadow in an abandoned marble quarry which would make a perfect spot for a picnic.
Drive to the top of Mt. Greylock
From May through November, you can drive to the top of Mount Greylock, the highest point in Massachusetts. At 3,491 feet above sea level, you can see 90 miles on a clear day. On the day we were there, we had a perfect view of Mt. Wachusett AND Stratton Mountain in Vermont. Visit the Veterans War Memorial Tower at the summit or grab a bite to eat at the Bascom Lodge.
Susan B. Anthony Birthplace Museum
Susan B. Anthony was a women’s rights activist who played a pivotal role in the women’s suffrage movement. The museum highlights the familial and regional influences which shaped Ms. Anthony’s early life. Although it was closed during our visit, I still enjoyed seeing the house where such an amazing woman was born.
This is a unique place because it is one of the few institutions in the country that combines a public art museum with academic programs.
This is a fancy art museum, but still welcomed our kids with a really great activity pack. They were given a free art pad and pencil to draw as well as activity card to find certain pictures that we could do as a scavenger hunt.
The outdoor grounds were so beautiful, they are sure to inspire your inner artist. You could spend the better part of a day just exploring the trails and sculptures outside which are free and accessible 24-7.
When I think of the Berkshires, I think of creative art, amazing food and good music. Beautiful places seem to inspire the creativity inside. For more theater and dance, check out Jacob’s Pillow or Shakespeare & Company.
I hope you liked this list of what to do in the Berkshires. What are you favorite places or places that I have missed? Let me know in the comments below.