Pittsfield, MA is known as the “Heart of the Berkshires” because its central location is geographically perfect for exploring that beloved mountainous region of Western Massachusetts. But beyond just using the town as a jumping-off point for other areas, there are actually many things to do in Pittsfield, MA, itself.
Why Visit Pittsfield?
Yes, that’s right — Pittsfield is rapidly growing, and now boasts a top-notch theatre to see plays, an art museum that also is an aquarium, unique shopping and food, cute hotels, plus loads of history. Does the name Herman Melville ring a bell? There’s so much to do for all ages, in all seasons. Let’s explore…
Things to Do in Pittsfield, MA
Here's an alluring list of ideas for things to do in Pittsfield, MA with adults or kids. This town in ther Berkshires of Western Massachusetts has much to offer.
Historic Buildings of Pittsfield
Because it was a bustling town way back in the 1800s, Pittsfiled, MA has stunning historic architecture -- much of which has been remodeled in creative ways that preserve its charm. Browse this article to see some highlights to watch for as you walk around town.
The Berkshire Museum
If you're looking for a truly eclectic museum for all ages, look no further than Pittsfield's Berkshire Museum. It has everything from an aquarium (including sparkly piranhas!), to fine art, to classical sculptures, to Asian artifacts, to taxidermy specimens, to an entire hands-on play and learning area for kids. Oh, and the color of green paint on the walls of the main gallery is spectacular.
Herman Melville's Arrowhead
Did you know that you can tour the very room in which Herman Melville wrote the classic novel, Moby Dick? Just a few minutes outside the center of Pittsfield sits Arrowhead: the home of the great American author. Take the guided tour to learn fascinating stories about the Melvilles and their friends.
Hotel on North
Wondering where to stay in Pittsfield? I highly recommend the Hotel on North, which is not only ideally siutated in the center of town, but also has absolutely delightful architectural details that draw from the building's history as a department store from the 1800s. The attached restaurant, Berkshire Palate, is yummy, too.
Shopping and Eating in Pittsfield
There is so much unique shopping to be done in Pittsfield! Being an English teacher, I particularly loved the store which sells giant framed posters of book spines, pictured here. This article also has tips on several places to eat and get beverages.
Barrington Stage Company
I was stunned at the quality of plays at the Barrington Stage Company. We saw a production of the musical, "Cabaret" which featured numerous Broadway and TV stars -- all for a fraction of what it would cost in New York City.
Attractions Less than an Hour from Pittsfield, MA
If you're willing to take a 30-40 minute drive north or south from Pittfield, you'll be rewarded with some of the top attractions in the state!
The Red Lion Inn: Stockbridge, MA
Talk about historic hotels -- the Red Lion Inn in picturesque Stockbridge, MA was founded in 1773 (!!!) and gives Norman Rockwell vibes, extraordinare. This spot is less than 30 minutes from Pittsfield, due south.
Mount Greylock
Looking for the highest point in Massachusetts? Mount Greylock is just half an hour north of Pittsfield, and you can even drive up to the top!
The Clark Museum: Williamstown, MA
A little over 30 minutes north of Pittsfield is Williamstown, MA: college town, and home of the classic Clark Museum. Top-notch paintings and art!
MASS MoCA: North Adams, MA
37 minutes north of Pittsfield in North Adams sits the sprawling playground of modern art that is MASS MoCA. You can spend a whole day there, for all ages.
Watch Planes at Great Barrington Airport
35 minutes south of Pittsfield sits the adorable small airport of Great Barrington, MA which has tiny planes whizzing in and out. If you bring kids, sometimes the pilots even let them sit in the cockpits!
Attractions an Hour from Pittsfield
There you have the list of Pittsfield attractions! Now, if you want to go further afield, it’s just one hour to drive south to Bash Bish Falls, the highest waterfall in Massachusetts. Just make sure you read that article to make a better choice than we did about which hiking route to take.
Heading one hour east, Northampton, MA has so much to see, as does nearby Amherst, MA. I particularly recommend the Eric Carle Museum of Picture Book Art in the latter town. If you’re driving back to Boston from Pittsfield, you can fold in those sights along the way.
Things to Do in Pittsfield, MA in Sum
For up-to-date listings on Pittsfield events and updates, make sure to check out the town’s official visitor site. So, which of these things to do in Pittsfield, MA (and its environs) are you most excited to do, or to have done? What’s missing from the list that I should add? Do share!
Want more? Check out my article on the similarly-named, yet quite different, town of Pittsburgh, PA!
The author, Lillie Marshall, is a 6-foot-tall National Board Certified Teacher of English, fitness fan, and mother of two who has been a public school educator since 2003. She launched Around the World “L” Travel and Life Blog in 2009, and over 4.2 million readers have now visited this site. Lillie also runs TeachingTraveling.com and DrawingsOf.com. Subscribe to her monthly newsletter, and follow @WorldLillie on social media!