If you’re looking for a fun and unique getaway, look no further than the Berkshires in Massachusetts. Once a sleepy region, it has quickly turned into a fantastic tourist destination.
Located in western Massachusetts, the Berkshires are renowned for their vibrant greenery, rolling hills, culture, and wide array of activities. Step into the outdoors for hiking, biking, and skiing before heading back to the area’s quaint towns for art galleries, museums, and historic landmarks.
With a list this long, you won’t run out of things to do in the Berkshires, whether you come during winter or summer. Read on to find out just what is waiting for you in the Massachusetts highlands.
What to Do in the Berkshires
To help you get started, here are the things to do in the Berkshires, Massachusetts, that will leave you wanting more.
1. Naumkeag
The Naumkeag house, a stunning historic Stockbridge estate, is often lauded as the best of the Berkshires. The 48-acre building draped in Gilded Age architecture is a step back in time mixed with modern bells and whistles.
The array of attractions here is endless. There are some charming gardens, including a Chinese-themed garden complete with a shrine. Also on the cards are a number of stunning vistas, as well as the idyllic Blue Steps, which often steal the show.
The Naumkeag house is also home to a variety of events, including a colorful spring festival, a mesmerizing lights show during winter, and a fun pumpkin show in October.
2. Tanglewood
Come here and ask a local where they’re going, and you’re likely to find out that all roads lead to Tanglewood. This is an open-air music venue that plays host to different acts that often have crowds of jazz, pop, classical, and rock lovers dancing for hours.
While the Boston Symphony Orchestra is an all-year-round fixture, Tanglewood has had acts like Ringo Starr, Earth, Wind & Fire, and more take the stage.
For the best experience, come during the summer. You can spend the day in awe of the stunning scenery of the rolling hills and end the night watching the stars dance in the clear, dark skies.
Experiencing Tanglewood is easily one of the best things to do in the Berkshires’ Lenox area.
3. Jacob’s Pillow
Have you heard of Jacob’s Pillow? It’s not a cozy cushion for your living room but rather a renowned dance center that inspires oohs and aahs from all who visit.
This picturesque venue has been a must-visit destination for dance enthusiasts since 1933. What’s so special about Jacob’s Pillow, you might ask?
Well, for starters, it’s the longest-running dance festival in the United States, showcasing an eclectic mix of dance styles ranging from classic ballet to contemporary hip hop. Whether you’re a seasoned dancer or just someone who wants to appreciate the art form, there’s something for everyone at Jacob’s Pillow. With a beautiful outdoor stage surrounded by lush greenery, it’s no wonder this place offers a truly unforgettable experience.
4. Mount Greylock
In Adams, you’ll find the nearly 3,500 feet Mount Greylock, the highest point in Massachusetts. Hiking Mount Greylock. At the summit, you’ll be able to take in 360-degree views of the beauty of the Berkshires and four other states.
From May to November, you can drive to the peak via the scenic Rockwell Road, with plenty of stops to admire the scenery.
Alternatively, come any time of the year, and you’ll be able to hike your way to the top. There are several hiking trails of various difficulties, meaning everyone from the novice to the experienced can get to the peak. If there’s a trail you must do, it’s the famous and stunning Appalachian Trail.
5. Norman Rockwell Museum
If you’re a fan of Americana and the art that captures it, you’ll definitely want to visit the Norman Rockwell Museum in Stockbridge. With over 100,000 pieces of artwork, many belonging to Norman Rockwell, this museum is chock-full of the iconic illustrations. These pieces capture the spirit of America’s small towns and everyday moments.
You’ll get lost in the whimsical scenes of families gathered around the dinner table, children playing outside, and neighbors coming together to celebrate the Fourth of July.
Outside of Rockwell’s incredible works, there are rotating exhibitions highlighting art from artists like Leo Lionni and Tony Sarg.
6. Clark Art Institute
Add more art exploration to your Berkshires’ trip by visiting the Clark Art Institute.
It’s a fabulous museum located in Williamstown and somewhat a hidden gem in Massachusetts. The Clark Art Institute is known for its impressive collection of European and American art. The works on display range from impressionist paintings to ancient sculptures.
But what sets this museum apart is its stunning architecture, especially the new Tadao Ando-designed building that has been earning rave reviews. Additionally, the gallery hosts several educational workshops that teach artists or art lovers of every level of experience all they need to know.
7. Skiing
While the East Coast is blessed with skiing opportunities in nearly every state, there aren’t many that can compare to the Berkshires. During winter, a number of incredible runs await skiers of all levels, from beginner to advance.
Among the very best skiing destinations here is Ski Butternut in Great Barrington. Acres on acres of snow, as well as lifts offering views of the nearby landscape, are perfect for zooming down from the summit.
Another good option here is Jiminy Peak Mountain Resort, located in Hancock. It has a good variety of beginner, intermediate, and advanced runs, so the whole family can join in on the fun. It also has lodging options if you want to spend the weekend in the Berkshires.
8. Berkshire Scenic Railway Museum
All aboard the Berkshire Scenic Railway Museum. Whether you’re a train enthusiast or just looking for a fun way to explore the Berkshires, this museum is a must-visit destination.
First, explore the history of railway transportation in the Berkshires before viewing the impressive showcase of vintage locomotives. Afterward, hop aboard the train as you wander around the picturesque countryside.
If you’re traveling with kids, or are a kid at heart, you can enjoy the fun experience of ringing the bell on a real train.
9. Hancock Shaker Village
Have you ever wondered what it would be like to go back in time to a simpler way of life? Perfect, you can experience a dive into the past by visiting the archaic Hancock Shaker Village.
This historic site offers a glimpse into the world of the Hancock Shakers, a religious community that lived in the area in the 18th and 19th centuries. Step into their shoes and experience the peacefulness of a lifestyle where simplicity and hard work are the norm.
The village also doubles as a farm, with a variety of crops being grown and livestock like sheep, lamb, cows, chickens, and more.
10. Hilltop Orchards
Hilltop Orchards is like a slice of heaven for apple lovers. This farm, located in Richmond, is a treasure trove for apple picking, thanks to over 20 varieties of apples.
While apple picking is a fall pastime, Hilltop Orchards is open all year round. So, you don’t have to wait until autumn to come here.
One of the best things to do in the Berkshires in the summer is hiking the 200-acre grounds and stopping for a taste of delectable cider. Afterward, you can take in the picturesque views of the Berkshire mountains. But before you leave, you have to try the institution’s crème de la crème — the cider donuts.
11. Pleasant Valley Wildlife Sanctuary
Visiting Lenox’s Pleasant Valley Wildlife Sanctuary is one of the best Berkshires activities. A nature lover’s paradise, this place is filled to the brim with an abundance of wildlife and stunning natural scenery.
The sanctuary is dotted with trails, all passing along some scenic points of interest, including dense forestry and tranquil ponds. Not to mention, some lead to stunning views of the valley.
While wandering through the winding trails, keep your eyes peeled for the different wildlife you’ll come across. Look down, and you’re likely to see small creatures hidden behind the shrubs. Look up, and you’ll see a number of birds flying high in the sky.
12. Shakespeare and Company
When you’re visiting a cultural hub like the Berkshires, you can’t just stop at art, dance, and music. You have to add some classic theater to your itinerary, and Shakespeare and Company in Lenox is your best spot for getting a dose of the Bard’s stories.
From the lively outdoor stages to the cozy indoor theaters, every nook and cranny of Shakespeare and Company oozes charm and personality. The theater caters to Shakespeare enthusiasts of all ages, with modern and traditional takes on English’s most beloved storyteller.
Aside from the fantastic shows, you’ll also have the opportunity to do behind-the-scenes tours.
Final Thoughts on the Top Berkshires Things to Do
From exploring history and art to hiking trails underneath lush forestry, the Berkshires have something for everyone. The highlands region of Massachusetts is home to various towns, each boasting a charm of its own.
If you’ve found yourself falling in love with any of the entries listed here, book lodging in the Berkshires and give yourself plenty of time to explore this beautiful region. You’re likely to find even more fun things to do in the Berkshires when you arrive!
