Why You Should Spend your Next Family Vacation in the Berkshires of Western Massachusetts

We had the most incredible family vacation in The Berkshires and Springfield of Western Massachusetts this summer! As someone who grew up along the eastern coastline, I know that when people think “Massachusetts Vacation,” the Cape and Islands are the first things that come to mind. This year we were looking for something a little different. The Berkshires region is known for its art, its gorgeous views, its museums, and its music, all things that we love. It is also surprisingly kid-friendly making it the perfect family destination.

Read on to find out more about why you should spend your next family vacation in the Berkshires.

Getting to the Berkshires

Whether you come from the Boston area or New York City, plan around 3 hours to get to The Berkshires. This will vary depending on where you decide to spend your trip since the Berkshires are made up of the entire westernmost part of the state. If you are arriving by air, the closest airport is actually in Albany, NY. It’s still about 60 miles away so plan your travel time accordingly. You can also grab the train. Amtrak’s Lake Shore Limited runs between Boston and Chicago, making a stop in Pittsfield.

While 3 hours can seem like a long time in the car with a 3-year-old, it was totally worth it. As soon as we crossed into the region (there is a charming wood green and gold sign that welcomes you to the Berkshires), we felt like we had been transported to another world. The air seemed a little cleaner, the trees looked greener and I felt just a little lighter. We were officially on vacation!

Where to Stay

Hotel on North

Pittsfield, MA

You know what they say, “location, location, location,” and Hotel on North has one of the best locations in The Berkshires of Western Massachusetts. Located on North Street (hence the name) in Pittsfield, this boutique hotel is right in the center of the region. If you’re doing a full tour of the Berkshires (about 90 minutes from top to bottom) that means you’ll only ever be about 30 to 40 minutes from the best shops, museums, music and theater venues, and restaurants that the area has to offer.

As soon as we pulled up in front of Hotel on North, I fell in love. Meticulously restored architectural features, mixed with exposed brick walls, tin ceilings, and decorative columns, all make for a stunning combination. Each room has a little library full of books that you can read during your stay. I picked up a book on the Salem Witch Trials and when I mentioned to JP, the hotel manager, that I hadn’t finished it, he told me to take it home!

Staying at Hotel on North felt like home. The beds were comfortable, the rooms spacious, and the staff welcoming. We slept soundly (not usually an easy feat when you have a toddler in the room) and in the morning we made delicious coffee while we got ready to start our day of exploring.

Hotel on North is very proud of its Berkshire roots and features work from local artisans and artists in the rooms, in the lobby and other public spaces, as well as in its gift shop, Dory & Ginger. It also has a playroom. While that didn’t seem like a big deal to me, when we asked Arielle what her favorite part of the vacation was without hesitation she said, “the playroom.”

What to Do

Hancock Shaker Village

Hancock, MA

Our first introduction to the Berkshires of Western Massachusetts was Hancock Shaker Village, a living history museum that brings the Shaker story to life. According to the National Historic Register, this 750-acre landmark in Hancock is the most comprehensively interpreted Shaker site in the world. It is also the oldest working farm in the Berkshires – meaning it is home to plenty of farm animals which had Arielle leaping for joy!

Here you’ll see 22 different buildings with woodworking and blacksmith presentations. Arielle enjoyed visiting the kids barn, full of interactive demonstrations of Shaker life such as learning how to milk cows and weave cloth. They also bring in artists to display their work, and you can watch live music and see demonstrations of Shaker dances. You can even take a yoga class with their resident goats!

Alex and I were amazed by the architecture of the museum’s Round Stone Barn, the only circular barn ever built by the Shakers that has drawn visitors like one of my favorite authors, Nathaniel Hawthorne.

The Norman Rockwell Museum

Stockbridge, MA

When you think of Norman Rockwell, I’ll bet his self-portrait on the cover of “The Saturday Evening Post” comes to mind. His contribution to the art world, though, as well as to American society, is what’s really on display at his namesake museum. Of course we loved seeing all 323 Post covers, in addition to a treasure trove of his other work. We also visited his studio which was transplanted from another part of Stockbridge to the museum site. On the walls next to his work, I enjoyed reading just how his illustrations captured both the human condition and political landscape of the early to mid-20th century.

One such instance was his painting, The Problem We All Live With, which addressed race in mid-century America. In the piece, Ruby Bridges, a six-year-old African American girl makes her way to an all white public school in 1960 as part of New Orleans school desegregation. She had to be escorted by four deputy U.S. marshals, also in the painting. While this history lesson can seem like it happened a long time ago, I was shocked to find out that Ruby Bridges is only 67 years old today.

If you don’t know the work, it’s extremely powerful, and I believe that may be part of the museum’s inspiration to include other exhibits focused on race that are on display now. As a mother, seeing Imprinted: Illustrating Race, allowed us to have an important conversation with Arielle through a medium she seems to enjoy and understand: art.

Berkshire Museum

Pittsfield, MA

This was the biggest surprise of the trip for me. The Berkshire Museum may look small on the outside, but on the inside it is full of fun activities and fascinating exhibits. I keep telling friends and family that it is like a children’s museum, science museum, art museum, history museum and mini aquarium all rolled into one. There were so many interactive pieces throughout, that Arielle never felt bored or restless – talk about a parent’s dream come true! I was interested in Living Ink: The Art of Tattoo where we got to see the beautiful work of tattoo artists around the world. Arielle loved designing her own butterfly tattoo! We also enjoyed Berkshire Based Artists and the Berkshire Innovators sections.

One common theme that was especially prevalent during our trip was the pride Berkshire residents have in their area, their fellow citizens, and all of their achievements. It was evident at the museums, at the hotel, and with everyone we met along the way, and the Berkshire Museum was no exception.

The Amazing World of Dr. Seuss

Springfield, MA

On the way back to Boston, we stopped at the Springfield Museums in Springfield, Massachusetts, about an hour from The Berkshires. They actually boast five museums in one and we could have spent the whole day exploring, but we had a mission: to find the Cat in the Hat. We found him at The Amazing World of Dr. Seuss, along with several other of his friends like Horton, The Grinch, and the Lorax.

We loved stepping in the door and feeling like we had been transported into another world, full of color and rhymes. The first floor is an interactive adventure that follows the life of Theodor Seuss Geisel (better known as Dr. Seuss) and the characters he created. The second floor is more adult-focused as we saw a recreation of Geisel’s office and living room. Another gallery is full of letters he wrote which included some of his famous creations. Alex and I grew up on Dr. Seuss books, and we’ve passed that on to Arielle, so this was a wonderful stop that the whole family enjoyed and the perfect way to end our family vacation.