There’s no one way to do the Berkshires. For some people, a visit to the Berkshires means spending time immersed in history. From visiting mansions that housed some of America’s greatest thinkers to taking in the gardens growing among historic ruins, a Berkshires getaway can mean stepping back in time.

For others, a visit to this area in western Massachusetts means taking in all kinds of arts and culture. Throughout the region, you’ll find many music and dance festivals, as well as art museums of all genres. And for some visitors, it means adventure. From soaring down the slopes to taking on whitewater rapids, visiting the Berkshires can really get your heart pumping.

Planning a trip to the Berkshires and wondering what to do? We’ve compiled a list of the best things to do in the Berkshires, from an art museum that will make you see art in a new light to thrill-seeking adventures. Check out the many Berkshires attractions on this list, and you’re bound to have an amazing time visiting this cultural hub!

The 15 Best Things to do in the Berkshires, MA

1. Enjoy the Music at Tanglewood

Located in the towns of Lenox and Stockbridge, Tanglewood Music Center has been the summer home of the Boston Symphony Orchestra since 1937. Tanglewood is one of the most beloved music festivals in the world. If you’re visiting in the summer, taking in the music at Tanglewood is one of the coolest things to do in the Berkshires.

Although you might imagine that the summer home of an orchestra would play all classical music, you’ll find genres of all types in the air around this historic venue. You’ll also listen to a litany of performers beyond the orchestra itself. 

But you come for the experience as much as the music itself. Long before a concert begins, you’ll often find people picnicking on the music center’s grounds. Tanglewood tailgating is a true Berkshires pastime! 

Tanglewood also offers free tours between July 1 and August 27. During the tour, you’ll get an insider’s look at the historic music center and learn all about the background of this magnificent place.

2. Go Whitewater Rafting

Whether you want to take it slow and breathe in that beautiful mountain air or you’d rather have a high-speed adventure, there are tons of ways to enjoy the great outdoors in the Berkshires. And Zoar Outdoor can help you enjoy either type of experience. 

Zoar Outdoor offers some of the coolest Berkshires activities, from canoeing to ziplining. Paddle your way down the Deerfield River with their whitewater rafting, kayaking, and canoeing trips. No matter what your experience level, Zoar Outdoor will get you out on the water safely. If you’re a beginner, you can take a lesson to up your skill level to get ready for the rapids.

Don’t want to take to the water? How about taking to the sky? Zoar Outdoor also has its own canopy tour that will take you high above Deerfield River Valley. You’ll soar through 11 zip lines, enjoy the view from two sky bridges, and whisk down three rappels. You can also get one of their Adventure Packages to take part in both the water-based and sky-based activities.

3. Visit the Norman Rockwell Museum

Known as the official state artist of Massachusetts, Norman Rockwell has a long legacy in the Bay State. The legendary cartoonist spent many years in the Berkshires, calling Stockbridge home. Today, Stockbridge offers a wonderful way to get to know the artist and one of the best things to do in the Berkshires.

The Norman Rockwell Museum houses the world’s largest collection of Rockwell’s work, including 998 original paintings and drawings. When you visit here, you can see all 323 of his “Saturday Evening Post” covers and uncover his unique social commentary. 

Also on-site is Rockwell’s studio, which is open to the public from May to October. Here, you’ll find all of his original art materials, his library, and many personal items. The museum proudly holds a collection of more than 100,000 items from the Norman Rockwell Archives, from photographs to fan mail. 

However, the museum is more than a place to admire this great artist. It’s dedicated to celebrating illustration as an art form in general. Within the museum, you’ll also see rotating exhibitions featuring illustrators and other artists of both the past and present.

If you want to dive deeper into Rockwell’s work, you can schedule a Gallery Tour. They are available daily, but book in advance as they often sell out as tours are limited to 25 people. For even more Rockwell history, you can also book a Studio Tour, which is even more limited in size, making reservations all the more crucial.

4. See the Bard at Shakespeare & Company

There’s a lot going on at Shakespeare & Company, which offers one of the coolest things to do in the Berkshires. Located in Lenox, Shakespeare & Company dates back to 1978. It was first housed in writer Edith Wharton’s historic home, The Mount.

Since 2000, it’s found a new home that holds its administrative offices, housing, rehearsal spaces, and four theaters, including its new 500-seat outdoor amphitheater, which just opened in 2021. Across the theaters, you’ll find shows of all kinds. 

Although Shakespeare is at the heart of the organization, it also puts on performances from more contemporary writers, as well as other classic bards. Beyond plays, you’ll also find other events here, like concerts.

Shakespeare & Company is also home to an award-winning education program. Students take part in innovative performances and workshops that help them hone their craft. Today’s students go on to become tomorrow’s Broadway stars!

5. Hike in Mount Greylock State Reservation

Mount Greylock stands proudly at 3,491 feet, making it the highest point in all of Massachusetts. From its peak, you can see as far as 90 miles, which paints quite a beautiful panorama. Hiking to the top offers one of the best sights in Massachusetts. 

However, you don’t actually need to hike to the top, as it is a particularly strenuous journey. At the Mount Greylock State Reservation, you can drive to the peak from May through September. 

But we especially recommend coming to this reservation in the fall. The route to the top is exceptionally beautiful when the fall foliage starts. In fact, there are many routes to take around the 12,000 acres of the park that offer stunning looks at Massachusetts’ famous foliage. 

There are also numerous hiking trails to take. Even if you don’t feel up to hiking all the way to the top of the peak, more paths are available that are better suited for hikers looking for a less challenging trek. If you visit in the winter, you can also enjoy the trails through snowmobiling and cross-country skiing. 

6. Spend a Day at Mass MoCA

Located in a restored 19th-century factory building in North Adams, there’s so much to do at Mass MoCA that it definitely deserves a spot on your Berkshires bucket list. It’s one of the largest centers for contemporary visual and performing arts in the US. When you visit here, you’ll find it’s different from any other art museum as it shows off art in unique ways.

While many art museums focus on just one form of art, you’ll find celebrations of music, sculpture, dance, film, photography, theater, and much more within MoCA’s walls. In addition to exhibits that make you question what you thought you understood about art, from roller coasters to walkways that create music, you’ll also be able to enjoy live performances of everything from silent films to cabaret. 

Oh, and did we mention all there is on its campus? Enjoy a meal from multiple restaurants with all different types of cuisines, treat yourself to a latte, or enjoy sampling your way through a microbrewery that spotlights locally malted grains and hops grown right in the Berkshires. It’s easy to spend a whole day at Mass MoCA.

7. Wander Around Pleasant Valley Wildlife Sanctuary

Located in Lenox, Pleasant Valley Wildlife Sanctuary is home to more than 1,000 acres consisting of forests, meadows, and wetlands. As you take the many trails here, you’ll explore unique ecosystems and walk along the slopes of Lenox Mountain to take in incredible views.

There are seven miles of trails to explore, each offering something different for every type of hiker. Take the path along Pike’s Pond for an easy stroll that just might introduce you to some beavers. 

Or check out the Lenox Mountain ridge on the Beaver Lodge Trails Loop. For those wanting something more challenging, check out the Overbrook Loop, where you can enjoy views of Mount Greylock, the Taconic Range, and the Catskills. 

In addition to hiking, there are also many programs and activities here that are fun for the whole family. Little ones will love the Nature Play Area, where they can build pretend fires, make gnome homes, or test their skills on the boulders, which hide some fun surprises. Other family-friendly events include nature walks and story times at Beaver Pond.

Meanwhile, those who want to experience the wildlife portion of this wildlife sanctuary can join its Birding Program, which is led by a skilled guide who knows just where to look. And if you’re visiting between spring and fall, you can take a guided canoe trip down the Housatonic River or the Berkshires lakes.

8. Sample the Goods at Hilltop Orchards

Now, we don’t necessarily want to say that Hilltop Orchards in Richmond has the best apple cider donuts in Massachusetts because we’re bound to get quite a few complaints. In the Berkshires alone, you also have the sweet treats at Barlett’s Orchard or Lakeview Orchards and so much more. 

After all, apple cider donuts are a true Massachusetts delicacy, and every person in the Bay State seems to have their favorite. (Personally, my favorite apple cider donuts in the state can be found at Peabody’s Brooksby Farm.)

However, it’s more than safe to say that Hilltop Orchards is home to among the best apple cider donuts in Massachusetts and perhaps all of the United States. But you’re going to want to go here for more than just the donuts. 

This 100-year-old, family-owned farm is one of the best Berkshires attractions, as you’ll find incredible views here. You can take one of the professionally built hiking trails or simply enjoy the vista from the patio. Or, if the weather is getting cold, you can warm up by the fireplace. 

In addition to apple cider donuts, you can also enjoy another apple-based treat: cider. Tour the cidery and then sample the goods. There’s regular apple cider for the kiddos, but adults can partake in some sips of the alcoholic variety. Wine tastings are also available on-site. 

9. Witness a Performance at Jacob’s Pillow

Perhaps one of the most famous things to do in the Berkshires behind visiting Tanglewood, Jacob’s Pillow in Becket is a dance center that puts on several dance-focused events throughout the year. Their most beloved event is likely their summer festival, which features nine weeks of performances, as well as pop-up performances, workshops, parties, exhibits, and much more. 

But don’t write off going to Jacob’s Pillow just because you’re visiting outside of the summer months. Jacob’s Pillow is one of the top things to do in the Berkshires year-round. Throughout the year, you can also see their Pillow Labs, where artists create breathtaking performances that will help you see all the storytelling capabilities of dance and view the medium in a brand-new way. 

With the goal of legitimizing dance as an honorable career for men, choreographer Ted Shawn founded Jacob’s Pillow in 1931. Since then, countless dancers have trained at this unique school. Outside of the festivals and events, you can also come tour the campus of Jacob’s Pillow, which is a National Historic Landmark.

10. Enjoy the Blooms at the Berkshire Botanical Garden

Located in the heart of the Berkshires in Stockbridge, the Berkshire Botanical Garden is one of the most unique things to do in the Berkshires. It was designed not to simply be a garden but to be a museum of living things. 

Across its 24 acres, you’ll find plant collections of all kinds, with a focus on those that are native to the Northeast. Enjoy the serenity of the Pond Garden, view the topiaries of Lucy’s Garden, step back in time at the historic 1937 Herb Garden, or take the iconic Daylily Walk. 

Little ones will adore spending time learning about the natural world in the Children’s Discovery Garden. The gardens are home to over 3,000 species and varieties of plants.

The botanical garden also offers workshops and classes for kids and adults alike that can help you grow your green thumb, learn to take care of yourself while caring for nature, and allow you to understand more about the native plants around you. In conjunction with the natural beauty of the gardens, the botanical gardens also feature rotating art exhibits.

11. Go Skiing at Jiminy Peak Mountain Resort

There’s never a bad time to go to Jiminy Peak Mountain Resort. But many people know it best for its winter activities. Jiminy Peak has skiing for all ages, whether you’re a beginner in need of a few lessons or someone who is looking to take on a Black Diamond. What’s even cooler is that, unlike other ski areas that typically shut down when the sun sets, this mountain resort gets lit up at night so that skiers and snowboarders can enjoy racing under the stars.

But whether you’re visiting when the weather heats up or when it cools down, visiting Jiminy Peak is one of the most fun things to do in the Berkshires. In the winter, you can hit the trails with a pair of snowshoes, while in the summer, you can enjoy mountain biking while taking in incredible views. Or challenge yourself with a hike up the mountain! 

Meanwhile, over at their Mountain Adventure Park, you’ll find adventures for the whole family. Race around on the Mountain Coaster, glide down the mountain on the Alpine Super Slide, experience thrills and chills on the Giant Swing, or fly through the air on the Soaring Eagle. From trampolines to ropes courses to rock climbing, there’s tons of fun to be had all summer.

For even more of a challenge, you can take on the Aerial Adventure Park, which will have you swinging from the trees on rope bridges, swinging logs, zip lines, and more. There are several courses to take for all different skill sets, which allows everyone to get in on the fun.

12. Step Back in Time at The Mount

Considered a National Historic Landmark, The Mount is a stunning country home that was designed by beloved author Edith Wharton. She felt this luxurious estate was her first real home. Today, visiting The Mount is one of the top things to do in the Berkshires.

This Lenox location dates back to 1902. Over in the Main House, you’ll find classic Italian and French decor that will place you back in the early 20th century. In the Library, you’ll discover books from Wharton’s personal collection, as well as a collection of her own works. You’ll also see how Wharton’s servants lived in the Service Wing, which shines a light on the lives of those who didn’t live the luxurious lifestyle others like Wharton lived. 

Just as impressive as the inside of the house are the gardens, which were designed to be rooms all on their own. From the sunken Italian Garden with its stone walls to the French Flower Garden with its vivid bursts of colors throughout, the gardens are filled with a unique beauty that you’re bound to get lost in. 

There are a variety of tour options available at The Mount, including a tour of the house and one of the gardens. However, you can also dive into the paranormal with their ghost tours. The Mount is also home to numerous events throughout the year, like NightWood, a sound and light experience that takes place around the holiday season and truly illuminates the estate’s beauty.

13. Explore the Grounds of Naumkeag

Once a country estate for the Choate family, Naumkeag is now one of the best things to see in the Berkshires. Located in Stockbridge, this historic home features a far different design from The Mount, but it’s just as stunning.

You could call Naumkeag a cottage, but you’ll find it’s different from any cottage you’ve seen before. Known for its Gilded Age splendor, the estate for this architectural marvel covers a massive 48 acres. You’ll find yourself getting lost in the breathtaking gardens around this cottage. However, what you experience here will vary based on the season.

In the summer, you can glimpse inside the historic 44-room house and explore the gardens. You can even schedule high tea in the house or take part in seasonal events, like Naumkeag’s Wine Walks, where a horticulturalist will be your guide.

In the fall, the grounds transform into the Incredible Naumkeag Pumpkin Show, which features over a thousand jack-o-lanterns and decorative pumpkins. In the winter, the estate changes again, this time to gear up for Winterlights, where the night is lit up by thousands of twinkling lights. And in the spring, there’s the Daffodil and Tulip Festival, where the gardens take center stage.

Naumkeag is closed to the public in between these events, so be sure to check their website to see what’s happening during your visit. 

14. Attend the Williamstown Theatre Festival

Are you a theater lover? If you’re visiting in the summer, attending the Williamstown Theatre Festival is one of the best Berkshires activities. This summer theater festival is held each year on the campus of Williams College in Williamstown. 

This Tony Award-winning festival is recognized for being a place where stars are born. Award-winning actors like Paul Giamatti, Alison Janney, and Sterling K. Brown all got their start at the festival.

Though the historic festival dates back to 1954, many things are changing with it that offer a different experience from years prior. In an effort to find a new model of theater that better treats the staff of the festival, the Williamstown Theatre Festival actually pulled away from theater in the summer of 2023.

Instead of world-premiere musicals and plays and beloved revivals, the festival went on in a different way. Events included cabaret, stand-up comedy, concerts from Tony Award winners, and readings and workshops by artists-in-residence. Suffice it to say, there was still plenty to do despite theater itself being conspicuously absent.

The festival will continue changing in the upcoming years, but it’s worth keeping an eye on it. Musicals or no, plays or no, the Williamstown Theatre Festival deserves a visit.

15. Enjoy Ashintully Gardens

Ashintully Gardens is a 120-acre estate and one of the best sights in the Berkshires. Located in Tyringham, the gardens are a piece of art, but they’re also a window into the area’s history.

In the early 20th century, a Georgian-style mansion that would be called the Marble Palace was built here. It wasn’t marble at all, but the pure white sand used for the stucco reflected the sunlight in a way that made it look like marble. 

Years later, gardens were added. They took 30 years to create as the house’s then-owner, composer John McLennan, wanted to build something truly incredible. 

All that remains of the Marble Palace are its massive Doric columns. When you visit the gardens, which are available to the public in summer and fall, you can follow a lovely woodland trail to see the ruins and the still-thriving gardens. 

There you have it! The 15 best things to do in the Berkshires. What’s your favorite thing to do in the Berkshires? Let us know in the comments!

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