The Berkshires, located in the undulating hills of western Massachusetts, offer various tourist attractions like their breathtaking beauty, profound historical culture, and vibrant art scene. Whatever the case may be, there’s always something for everyone be it a nature lover or someone who loves history.
So, in this article, we present 20 things you must do when in The Berkshires, Massachusetts. Hope it’s fun to read!
1. Discover Tanglewood
Tanglewood is an exceptional place situated in the Berkshires area of Massachusetts known to be one of the most amazing cultural destinations due to its special appearance and outside music performances. Here you will find a combination of classical concerts, jazz performances, and popular songs that give it a unique character as a place for music lovers.
The world’s greatest concerts are held at this place among others such as Shed or Seiji Ozawa Hall where you can listen to music and enjoy it like no other venue in existence.
2. Immerse Yourself In Jacob's Pillow
Jacob's Pillow, situated in the Berkshires of Massachusetts, is an acclaimed site for dance festivals and cultural heritage. It is a fantastic mix of displays and exercises. This historic site is known as a premier place in the globe for world-class dance.
Visitors here will get to see several types of dances like ballet, modern dances, jazz, and others. The place has beautiful gardens, works of art, and old buildings that make it more beautiful to the visitors. In addition to shows Jacob’s Pillow also has workshops, talks, and other related activities that are interactive with the audience.
3. Uncover The Wonders Of MASS MoCA

MASS MoCA (Museum of Contemporary Art in Massachusetts) has become recognized as one of the biggest centers dedicated to visual and performing arts which are contemporary. As such, it is an active learning center built on a series of factory structures from the 19th century that offers vivid room for innovative artwork.
This is a home to numerous artistic works initially created by solo artists before they became globally popular. These include sculptures meant for display in homes or galleries, ordinary items transformed into masterpieces through innovative design methods, and buildings that complement their structure and style.
4. Explore The Beauty Of Mount Greylock State Reservation
Mount Greylock State Reservation is an adventurer's paradise and a nature lover's playground located in the Berkshires, Massachusetts. Standing at the highest point in Massachusetts, one can behold 90 miles farthest clear markings of the mountains’ neighbouring hues on a good day.
There are different genres of hiking trails in the reserve ranging from easy strolls to hard climbs accommodating all kinds of travelers. On top of it stands the Massachusetts Veterans War Memorial Tower; this tower was made to remember people who have battled for their land.
5. Explore Berkshire East Mountain Resort
Berkshire East Mountain Resort is the ultimate adventure destination in the Berkshires, Massachusetts. It provides various activities for thrill-seekers and nature lovers throughout the year. In winter months, there are several trails for skiers and snowboarders at this resort that are meant for individuals from different backgrounds.
When the snow melts, activities like zip-lining, mountain cycling, and white-water rafting among others take place at Berkshire East. However, while people enjoy scenic chair lifts or even mountain coaster rides, they can also engage in numerous hiking trails that exist.
6. Wander Through Berkshire Botanical Garden

The Berkshire Botanical Garden situated in the Berkshires, Massachusetts, is the ultimate destination for all botany enthusiasts. Spread over a total area exceeding 24 acres, this beautiful garden acts as an escapade into the field of horticulture with an array of flora that includes both local New England varieties and imported blossoms.
Here, people who visit this place are free to roam around well-designed gardens including perennial borders, herb gardens, and woodland trails which all come with their distinct colors throughout different seasons. Additionally, there are educational programs, workshops as well as seasonal events which help people of all ages to learn more about it.
7. Relax At Miraval Berkshires Resort & Spa
Miraval Berkshires Resort and Spa can be your ideal destination if you want to have relaxation, mindfulness, and adventure in equal measures in life. The historic Berkshires of Massachusetts is one place that offers a genuine wellness retreat.
At Miraval, you can enjoy a total immersion in a holistic experience where peace meets your personal growth. Various activities such as yoga and meditation sessions, and outdoor adventures including hiking or horseback riding with a view of feeding both the body and spirit are available for guests visiting this resort.
Having the best professional in the field is one of the factors that lead to the creation and maintenance of top-level spas. Buffet houses including those found in Africa serve almost all types of clients who deserve the best treatment according to their needs. Plus there’s gourmet food served at Miraval that matches its theme related to eating consciously; gourmet meals go well beyond just being nourishing.
8. Hit The Slopes At Bousquet Mountain Ski Area
In the middle of Massachusetts’ Berkshires lies Bousquet Mountain Ski Area, an extraordinary and worshipped destination for nature lovers. As one of the country’s oldest ski areas, it provides a delightful combination of classical New England skiing with up-to-date facilities.
During winters, this mountain is home to diverse tracks that suit every ability including slants that are soft for amateurs and complicated paths for experienced skiers and snowboarders. Besides downhill skiing, Bousquet offers night skiing as well as snow tubing as well as a comfortable lodge where visitors can go get warm and take some drinks.
9. Explore The Berkshire Museum

Berkshire Museum is a wonderful place in the Berkshires where you can experience art, history, and natural science. This family-friendly museum offers fun things to do in the entire country.
One of the most fascinating parts of this collection is the "Cabinet of Curiosities" where some interesting objects can be seen from all over the world. It has things like fossils, ancient Egyptian antiques, and other memorabilia.
There are also constantly changing art displays featuring local and international artists as well as interactive science sections that pique the interest of young minds. Aside from its permanent galleries, it also holds many special programs throughout the year including workshops, events, etc.
10. Delve Into The Clark Art Institute
A globally-renowned еxhibitory place with a renowned art curriculum is The Clark Art Institute. With masterpieces like Renoir, Degas, and Sargent, among others, The Clark possesses an extraordinary assortment of European and American paintings, sculptures, as well as decorative arts in general.
Beautifully designed galleries stand beside vast grounds with walking trails, outdoor installations, and marvelous views of the surrounding hills that the museum is beautifully complemented by. In addition to its permanent collection, it might house rotating exhibitions, educational programs and special events that make it a liveliness place.
11. Tour Herman Melville's Arrowhead
For American history buffs and literature devotees alike, Hermann Melville’s Arrowhead is a historic landmark not to be missed. The famous writer Herman Melville lived there between 1850 and 1863 years in which he produced his masterwork "Moby-Dick" in this 19th-century farmhouse.
In addition, Arrowhead visitors can see the well-preserved home that gives a deep inside look into Melville’s life as well as a place where he drew inspiration for the books he wrote. You will get a tour around the house including studies done by Melville himself as well as roaming the outdoors with an ample view of the berks hills which were once an everyday sight with Herman.
12. Step Into Hancock Shaker Village

Nestled within Massachusetts's beautiful Berkshire Hills amidst lush greenery, Hancock Shaker Village serves as an open-air museum showing what life was like for members of this utopian community that espoused simplicity and communal living among other things.
With more than 20 historical structures such as the famous round stone barn on over 750 acres of land, it is scenic. Various clubs volunteer their services to offer interactive exhibits, and practical workshops and show viewers how traditional crafts such as carpentry, pottery, or agriculture are performed.
Additionally, there are seasonal events at the village where people can learn more about Shaker culture with farm-to-table dining experiences available at our restaurant on-site within guided tours offered during certain times of the year.
13. Ascend Monument Mountain
Located in the Berkshires, Massachusetts, Monument Mountain is a must-see for both naturalists and those interested in history. The iconic natural feature provides a variety of picturesque hiking pathways that finish at stunning sites with views looking down upon the Housatonic River Valley as well as onto adjacent Berkshire Hills.
The Hickey and Peeskawso Peak Trails, probably the oldest and most popular ones, take hikers among areas of thick forests and rocky cliffs until they reach the top from where you can see views of great distance. It has also a rich literary past, mostly because it was an inspiration to famous authors such as Nathaniel Hawthorne or Herman Melville.
14. Discover The National Shrine of the Divine Mercy
From all over the world, pilgrims and visitors flock to the National Shrine of the Divine Mercy as their spiritual and calming destination. This good-looking sanctuary is given to Divine Mercy devotion, and it provides a tranquil place of prayer, meditation, and adoration.
A quiet Lourdes Grotto, life-sized Stations of the Cross, and a tall Divine Mercy statue are among some impeccably landscaped grounds that encircle the shrine. Here visitors can go for daily masses, take part in Chaplet of Divine Mercy, or just relish its peaceful atmosphere.
15. Explore The Legacy Of Chesterwood

Chesterwood is a former summer residence and studio of esteemed sculptor Daniel Chester French who is best known for creating the famous statue of President Abraham Lincoln in Lincoln Memorial, Washington D.C. This location offers visitors a unique taste of art, history, and nature.
On exploring this well-preserved estate, you can visit French's studio where some of his most famous pieces were born as well as view his sculptures and models. The home itself is an exquisite example of Colonial Revival architecture that sits amid carefully tended gardens and walking paths moving through quiet Berkshires.
16. Embark On A Journey through Mount Greylock State Reservation
The highest point in Massachusetts, Mount Greylock State Reservation presents surrealistic all-round views that go as far as ninety miles on a clear day. This makes it a common place for hikers, photographers, and anyone who wants to experience the magnificence of this region.
The reservation offers over 70 miles of hiking trails with a section of the renowned Appalachian Trail for different levels of hikers. Visitors can also picnic, camp, and engage in winter sports such as snowshoeing or cross-country skiing at this place besides hiking.
At the top, there stands an iconic War Memorial Tower in tribute to the veterans from Massachusetts, which adds some historical element to its natural wonder.
17. Explore The Prestigious Grounds Of Williams College
For history, architecture, and culture buffs a trip to Massachusetts’ Berkshires’ Williams College is paramount. This institution was established in 1793 as one of America's oldest and most revered liberal arts colleges.
The campus features a mix of ancient and contemporary structures placed within sight of the captivating Berkshire Mountains. There are also beautiful landscapes to peruse at this learning center along with such fun activities like visiting an amazing art museum housing more than 15,000 pieces among other galleries with attractions about Williams College itself and attending theatrical performances at the ‘62 Center for Theatre and Dance.
18. Step Into The World Of Shakespeare & Company

Shakespeare & Company is a well-known theater organization that caters to the cultural needs of both visitors and inhabitants. This place is known for its high-quality productions, both Shakespearian and modern-day plays with universal themes.
Within its lovely grounds, it has several theatres where plays are staged thus creating a more personal involvement between the audience and the performing artists. In addition to these presentations, Shakespeare & Company also avails educational undertakings, and workshops among other events hence making it a living center for artistic activities in the Berkshires.
19. Stroll Along Ramblewild Adventure Park
Ramblewild Adventure Park can be located at the height of the forest trees where all ages are welcome to have fun. The park offers a unique experience with its high ropes course, zip line, and walking trail providing a unique adventure through the forest canopy.
From beginner to expert levels, every individual will find something challenging awaiting them within Ramblewild’s boundaries. You can look forward to climbing, balancing, traversing suspension ropes, and zipping up between trees all day long. What’s more important is that it does not disturb nature as its construction lasts until the last moment itself.
20. Explore The Wonders Of Pleasant Valley Wildlife Sanctuary
The Pleasant Valley Wildlife Sanctuary, the site of this place is heaven for nature lovers and outdoor buffs who want to use or allusion to it. Spanning more than a thousand acres, it comprises various forests, wetlands, and meadows that can be explored.
Diverse wildlife including birds, beavers, and native fauna are found here on trails that are well-kept so that visitors can take peaceful hikes. In addition to that the educational programs as well as guided tours make it a splendid place for family outings and individuals who want to understand better about their surroundings.