Best Things to Do in the Berkshires, MA: 12 Berkshire Attractions

by Jen
Best Things To Do in the Berkshires, MA
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Are you planning a trip to the Berkshires, Western Massachusetts? Here are some of the most unique and adventure-filled things to do in the Berkshires. These picturesque landscapes, crystal-clear lakes, and cultural attractions are sure to make for a memorable vacation.

The Berkshires of Western Massachusetts are nestled in the heart of New England. This place beckons travelers with a harmonious blend of natural beauty, cultural richness, and historical charm. This region is known for its rolling hills, scenic trails, and quaint towns. It is a year-round destination that offers a unique blend of relaxation and adventure. This makes it a perfect escape from the hustle and bustle of city life.

The Berkshires are a treasure trove of experiences waiting to be discovered. From the vibrant arts scene to the plethora of outdoor activities, from the historic homes to the farm-to-table dining, there’s a wide array of things to do in the Berkshires. Whether you’re an art enthusiast, a history buff, a nature lover, or a foodie, you’ll find your heart’s desire in the Berkshires.

In this guide, we’ll explore the best things to do in the Berkshires. We’ll be drawing on local insights and hidden gems to help you craft the perfect itinerary. We’ll delve into the region’s rich history, explore its vibrant arts and culture scene, and discover the natural beauty that makes the Berkshires one of the best places to visit in the United States.

So bring your sense of adventure and join us as we embark on a journey through the Berkshires, a place where every season brings new wonders, and every visit leaves you longing for more.

The top places to visit in the Berkshires, MA right now
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Best Places to Visit in the Berkshires: Your Ultimate Guide to Western Massachusetts

Are you ready to jump into all the best places to visit in the Berkshires? This region is home to a myriad of attractions, each offering a unique perspective on what makes the Berkshires so special.

From the historic homes that tell tales of a bygone era to the natural wonders that inspire awe and admiration, there are endless places to visit in the Berkshires that never cease to amaze. Here are the top 12 places you must visit in the Berkshires, Western MA:

1. Visit the Norman Rockwell Museum, Stockbridge

Looking for the best things to do in the Berkshires for art lovers? Don’t miss this one! Immerse yourself in the world of one of America’s most beloved artists at the Norman Rockwell Museum. It is located in the picturesque town of Stockbridge, where Rockwell spent the last 25 years of his life. This museum houses the world’s most extensive collection of original Rockwell art.

As you wander through the galleries, you’ll be transported back in time, experiencing the world through Rockwell’s eyes. His vivid illustrations, which so accurately depict American life, are more than just paintings; they’re stories frozen in time, each one a snapshot of a bygone era. From his iconic Saturday Evening Post covers to his powerful Four Freedoms series, Rockwell’s art captures the spirit of America in a way few artists have managed to replicate.

The museum offers more than just Rockwell’s art. It also provides a glimpse into the artist’s life and process. You can visit his original studio, which was moved to the museum grounds. They also preserved it exactly as he left it, complete with his paintbrushes, palette, and unfinished works.

Whether you’re an art enthusiast or just a casual observer, the Norman Rockwell Museum offers a fascinating look at American history through the eyes of one of its greatest illustrators. It’s one of the best places to visit for anyone exploring the Berkshires.

The Norman Rockwell Museum in the Berkshires offers a captivating glimpse into American history through iconic illustrations.
The Norman Rockwell Museum in the Berkshires offers a captivating glimpse into American history through iconic illustrations.

2. Enjoy an open-air concert at Tanglewood, Lenox

Steeped in musical heritage and set amidst the natural grandeur of the Berkshires, Tanglewood in Lenox is not just a concert venue, but a cherished summer tradition. As the summer home of the Boston Symphony Orchestra, this iconic venue has been a cornerstone of the Berkshires’ cultural scene for over 80 years and is coined by many as one of the best places to visit in the Berkshires.

Set against the backdrop of the stunning Berkshire Hills, Tanglewood offers a unique blend of natural beauty and musical excellence. The venue is known for its open-air concerts, where music lovers can spread out a picnic blanket on the lawn and enjoy world-class performances under the stars. From classical symphonies to contemporary pop concerts, Tanglewood’s diverse line-up ensures there’s something for every musical taste.

Tanglewood is also a fantastic place to learn. The Tanglewood Music Center, the venue’s educational arm, offers programs for talented young musicians and hosts public masterclasses and rehearsals.

Whether you’re a seasoned concertgoer or a first-time visitor, Tanglewood is one of the best places to visit in the Berkshires for an unforgettable musical experience. So, pack a picnic, bring a blanket, and prepare to be swept away by the magic of the Berkshires.

The venue hosts open-air concerts where music lovers enjoy world-class performances on the lawn with picnic blankets.
The venue hosts open-air concerts where music lovers enjoy world-class performances on the lawn with picnic blankets.

3. Explore the Appalachian Trail in the Berkshires

For those who crave the great outdoors, the Appalachian Trail is one of the best places to visit in the Berkshires. This iconic long-distance hiking trail stretches over 2,000 miles from Georgia to Maine. It offers some of its most scenic sections in the heart of the Berkshires.

The trail winds its way through the region, taking hikers through lush forests, across babbling brooks, and up rugged mountains. Along the way, you’ll be treated to panoramic views of the Berkshire Hills and the surrounding countryside. Whether you’re an experienced hiker looking for a multi-day adventure or a casual walker seeking a peaceful stroll, the Appalachian Trail has something to offer. 

One of the trail’s highlights in the Berkshires is Mount Greylock, the highest point in Massachusetts. The climb to the summit is challenging, but you’ll be rewarded with panoramic views that stretch as far as Vermont and New York on a clear day. At the summit, you’ll also find the Massachusetts Veterans War Memorial Tower, a poignant tribute to the state’s fallen soldiers.

Hiking the Appalachian Trail is one of the most unique things to do in the Berkshires, taking you on a journey through nature and offering a sense of peace and tranquility that’s hard to find in the modern world. Lace up your hiking boots, pack your backpack, and set off on an adventure that you’ll remember for a lifetime.

Hiking the Appalachian Trail in the Berkshires offers unique peace and tranquility in nature.
Hiking the Appalachian Trail in the Berkshires offers unique peace and tranquility in nature.

4. Visit the Blossoming Paradise of the Berkshire Botanical Garden

If you’re searching for the best things to do for families in the Berkshires, look no further than the Berkshire Botanical Garden in Stockbridge. This 15-acre living museum of stunning flora is one of the oldest public gardens in the Northeast. It’s a place where nature, art, and education intertwine, offering a tranquil retreat for visitors of all ages.

The garden is home to over 3,000 species and varieties of plants, meticulously arranged in more than 20 separate gardens. Each garden has its own theme, from the charming Cottage Garden filled with old-fashioned favorites to the Wetland Garden showcasing plants that thrive in water-logged conditions. The diversity of the gardens ensures a riot of color and a wealth of beauty in every season.

The Berkshire Botanical Garden is also a center for education, with a range of workshops, lectures, and classes for both adults and children. Whether you’re a seasoned gardener or a curious novice, you’ll find plenty to learn and explore.

The garden hosts a variety of events throughout the year, including art exhibitions, plant sales, and the much-anticipated Harvest Festival. No matter when you visit, there are always things to do at the Berkshire Botanical Garden, offering a peaceful and inspiring experience that celebrates the beauty and diversity of the natural world.

The garden houses 3,000+ plant species in 20+ themed gardens, from charming Cottage Garden to Wetland Garden.
The garden houses 3,000+ plant species in 20+ themed gardens, from charming Cottage Garden to Wetland Garden.

5. Relax at Bash Bish Falls, Mount Washington

For an awe-inspiring encounter with nature, make your way to Bash Bish Falls, one of Massachusetts’ most spectacular natural wonders. Located in the town of Mount Washington, near the border with New York, this waterfall is the highest in the state, cascading dramatically over a series of glistening rocks.

The journey to the falls is a rewarding experience. A scenic hike through the verdant Bash Bish Falls State Park leads you to the waterfall. As you traverse the winding trail, you’ll be surrounded by the tranquil beauty of the forest, with its diverse mix of flora and fauna.

Upon reaching the falls, you’ll be greeted by the sight of water tumbling down a steep series of rocks, creating a misty veil that shimmers in the sunlight. The pool at the base of the falls, encircled by large rocks, offers a serene spot to relax and enjoy the view.

Bash Bish Falls is not just a summer destination. Each season paints the falls in a new light, from the vibrant greens of spring to the fiery hues of autumn, and even the icy spectacle of winter, making it one of the best things to do in the Berkshires all year round.

If you’re an avid hiker, a nature photographer, or simply someone who appreciates the beauty of the natural world, Bash Bish Falls is one of the coolest places to visit in the Berkshires.

Bash Bish Falls: A cool must-visit for hikers, photographers, and nature lovers in the Berkshires.
Bash Bish Falls: A cool must-visit for hikers, photographers, and nature lovers in the Berkshires.

6. Visit the Modern Art Mecca at Mass MoCA, North Adams

For a unique place to visit in the Berkshires, you’ll want to visit this top Massachusetts attraction. Housed in a sprawling 19th-century factory complex, Mass MoCA (Massachusetts Museum of Contemporary Art) is one of the largest centers for contemporary visual and performing arts in the United States.

The museum’s vast, flexible space allows for large-scale and complex installations that are nearly impossible to realize in conventional museums. As you wander through the galleries, you’ll encounter a diverse array of thought-provoking art, from immersive installations to towering sculptures and innovative multimedia works.

Mass MoCA is also home to long-term exhibitions, including a 25-year retrospective of wall drawings by Sol LeWitt and a massive landscape installation by Anselm Kiefer. The museum’s performing arts program is equally impressive, featuring dance, film, music, and theater performances throughout the year.

Whether you’re an art enthusiast or just looking for the best places to visit in the Berkshires, the Mass MoCA is a must-visit. With its array of workshops, educational programs, and community events, it’s a place where art comes to life in exciting and unexpected ways. It’s a place to explore, to engage, and to be inspired.

Mass MoCA is a must-visit for art enthusiasts, offering workshops, programs, and community events that bring art to life.
Mass MoCA is a must-visit for art enthusiasts, offering workshops, programs, and community events that bring art to life.

7. Enjoy the outdoors at Mount Greylock State Reservation

For incredible views and some of the best hikes in the Berkshires, head to Mount Greylock State Reservation. As the highest point in Massachusetts, Mount Greylock stands as a majestic beacon in the heart of the Berkshires, offering unparalleled vistas and a wealth of recreational opportunities.

The reservation covers over 12,000 acres, with trails that cater to all levels of hiking ability. The most adventurous can take the challenging trail to the summit of Mount Greylock, where they’ll be rewarded with panoramic views that stretch as far as 90 miles on a clear day. On the summit, you’ll also find the Massachusetts Veterans War Memorial Tower, a poignant tribute to the state’s fallen soldiers.

Mount Greylock is also a popular spot for picnicking, camping, and bird watching, making it one of the best places to visit in the Berkshires for families. In the winter, it becomes a playground for cross-country skiing and snowshoeing.

If you’re seeking a challenging hike, a peaceful picnic spot, or simply a place to marvel at the beauty of nature, Mount Greylock State Reservation offers something for all to enjoy. It’s easy to see why this is one of the best places to visit in western Massachusetts!

Mount Greylock is a family-favorite for picnicking, camping, bird watching, and winter sports.
Mount Greylock is a family favorite for picnicking, camping, bird watching, and winter sports.

8. Explore the Berkshire Scenic Railway Museum, Lenox

Calling all train lovers! All aboard for a nostalgic journey at the Berkshire Scenic Railway Museum in Lenox. This museum is one of the best places to visit in the Berkshires for train enthusiasts and history lovers alike. It offers a unique glimpse into the region’s rich railroad history.

Housed in the beautifully restored 1903 Lenox Station, the museum features a collection of historic railroad equipment and memorabilia. You can explore vintage passenger cars, admire meticulously restored locomotives, and browse exhibits filled with old photographs, maps, and artifacts.

The highlight of any visit is a ride on the museum’s Hoosac Valley Service. This scenic train ride takes you on a leisurely journey through the picturesque Berkshire countryside, with knowledgeable guides providing commentary along the way. It’s a wonderful way to experience the beauty of the Berkshires while stepping back in time.

The Berkshire Scenic Railway Museum is a tribute to the golden age of rail travel and the role it played in shaping the region. It’s a place where history comes to life, offering a fun and educational place to visit in the Berkshires for all travelers to enjoy.

A must-visit for train enthusiasts and history lovers, offering a unique glimpse into the Berkshires' rich railroad history.
A must-visit for train enthusiasts and history lovers, offering a unique glimpse into the Berkshires’ rich railroad history.

9. Relax at Pontoosuc Lake, Pittsfield

If you’re looking for relaxing things to do in the Berkshires, look no further than the Pontoosuc Lake in Pittsfield. This beautiful 480-acre lake is a popular destination for both locals and visitors. It offers a variety of recreational activities and stunning views of the surrounding Berkshire Hills.

In the warmer months, the lake is a hub for water-based activities. You can rent a kayak or paddleboard and explore the lake at your own pace or take a leisurely swim in the designated swimming areas. The lake is also a popular spot for fishing, with species like largemouth bass, northern pike, and various types of trout.

If you prefer to stay on land, there are plenty of options too. Several parks and picnic areas surround the lake, providing a perfect setting for a relaxing lunch with a view. There are also several trails around the lake, offering peaceful walks with beautiful views of the water.

In the winter, Pontoosuc Lake transforms into a winter wonderland, with activities like ice fishing and snowmobiling.

If you’re an active adventurer or just looking for a peaceful spot to unwind, Pontoosuc Lake offers a little slice of paradise. As such, I recommend this beautiful place in the Berkshires to everyone I meet.

Pontoosuc Lake in Pittsfield is a serene destination in the Berkshires for recreation and stunning views.
Pontoosuc Lake in Pittsfield is a serene destination in the Berkshires for recreation and stunning views.

10. Experience a live performance at the Berkshire Theatre Group

Experience the magic of live performance at the Berkshire Theatre Group, one of the largest arts organizations in the region. With venues in both Stockbridge and Pittsfield, this acclaimed group offers a rich and diverse program of theatre, music, dance, and more. It’s no wonder that it’s one of the best places to visit in Massachusetts.

The group’s flagship venue, the Colonial Theatre in Pittsfield, is a beautifully restored historic building that hosts a variety of performances, from Broadway musicals to contemporary dance. The theatre is known for its stunning architecture, excellent acoustics, and intimate atmosphere, making every performance a special experience.

In Stockbridge, the Fitzpatrick Main Stage and the Unicorn Theatre offer a more intimate setting for plays and musicals. This includes both classic works and new productions. The group also runs a comprehensive education program, offering workshops and performance opportunities for young people.

The Berkshire Theatre Group offers an unforgettable cultural experience for all. It’s a place where stories come to life, where music fills the air, and where every performance is a celebration of creativity and talent. Don’t miss this attraction on your next trip to the Berkshires!

Berkshire Theatre Group: A magical arts destination in Massachusetts, offering diverse programs in Stockbridge and Pittsfield.
Berkshire Theatre Group: A magical arts destination in Massachusetts, offering diverse programs in Stockbridge and Pittsfield.

11. Explore the Canoe Meadows Wildlife Sanctuary, Pittsfield

Looking for the most beautiful places to visit in the Berkshires? Escape to the tranquility of nature at Canoe Meadows Wildlife Sanctuary in Pittsfield. This 262-acre sanctuary, managed by Mass Audubon, offers a peaceful retreat with its diverse habitats, including woodlands, wetlands, and fields.

The sanctuary’s three miles of well-marked trails are perfect for a leisurely walk or a quiet hike. As you wander through the sanctuary, keep your eyes peeled for the many species of wildlife that call it home. From beavers and otters in the wetlands to a variety of birds in the woods and fields, Canoe Meadows is a haven for wildlife.

Birdwatchers will particularly enjoy the sanctuary, which is home to more than 200 species of birds throughout the year. In the summer, the sanctuary’s fields are a breeding ground for bobolinks and other grassland birds.

The sanctuary also offers a variety of educational programs and workshops, aimed at promoting understanding and conservation of the local environment, making it one of the best things to do in the Berkshires for families.

Whether you’re a nature lover, a birdwatcher, or just someone seeking a peaceful retreat, Canoe Meadows Wildlife Sanctuary offers a slice of wilderness in the heart of the Berkshires.

Canoe Meadows Wildlife Sanctuary: A serene retreat for nature lovers, birdwatchers, and seekers of peaceful wilderness.
Canoe Meadows Wildlife Sanctuary: A serene retreat for nature lovers, birdwatchers, and seekers of peaceful wilderness.

12. Visit The Clark Art Institute, Williamstown

Art lovers should not miss a visit to The Clark Art Institute in Williamstown. Known simply as “The Clark,” this museum is renowned for its impressive collection of European and American art. It is housed in a stunning setting that combines galleries with expansive outdoor spaces.

The museum’s collection spans centuries, from Renaissance masterpieces to contemporary works. Highlights include paintings by masters such as Renoir, Degas, and Homer, as well as an extensive collection of beautiful American decorative arts.

The Clark is also a research and academic center, with a robust program of exhibitions, lectures, and workshops. Whether you’re an art scholar or a casual visitor, you’ll find plenty to explore and learn.

The Clark’s 140-acre campus is a masterpiece in itself, featuring walking trails, a reflecting pool, and outdoor installations. It’s the perfect place to enjoy art in the context of the natural beauty of the Berkshires.

With its world-class art collection and its commitment to research and education, it’s easy to see why The Clark Art Institute is one of the best places to visit in the Berkshires.

Don't miss The Clark Art Institute - a renowned museum with an impressive collection of European and American art.
Don’t miss The Clark Art Institute – a renowned museum with an impressive collection of European and American art.

Frequently Asked Questions (FAQs) about the Best Things to Do in the Berkshires, Massachusetts

Looking for more information on the best things to do in the Berkshires, MA? Here are some popular questions (and answers) I get that will help you plan your trip to the Berkshires:

What is the Berkshires best known for?

The Berkshires, a picturesque mountain range in western Massachusetts, is best known for its cultural attractions, scenic beauty, and recreational activities. Here’s what stands out:

  1. Cultural sights: The Berkshires are a hub for the arts. The Tanglewood Music Festival in Lenox is the summer home of the Boston Symphony Orchestra and hosts world-class musical performances. The region is also home to renowned theaters like the Williamstown Theatre Festival and Jacob’s Pillow, a historic dance festival and school.
  2. Art museums: Art enthusiasts flock to the Massachusetts Museum of Contemporary Art (MASS MoCA) in North Adams, one of the largest centers for contemporary visual and performing arts in the U.S. The Norman Rockwell Museum in Stockbridge, dedicated to the iconic American illustrator, is another highlight.
  3. Natural beauty: The area is characterized by its rolling hills, deep forests, and beautiful lakes, making it a favorite among nature lovers. The scenic beauty especially comes alive during the fall foliage season, attracting visitors from all over.
  4. Outdoor activities: The region offers numerous hiking trails, including portions of the Appalachian Trail. Winter brings opportunities for skiing and snowboarding at areas like Jiminy Peak.
  5. Historic sites: The Berkshires is dotted with historic homes and sites, such as The Mount, the former home of novelist Edith Wharton.
  6. Spa retreats: Known for wellness and relaxation, destinations like Canyon Ranch in Lenox provide luxurious spa experiences.
  7. Local cuisine: The Berkshires boasts a rich culinary scene with farm-to-table restaurants, local breweries, and charming cafes.

In essence, the Berkshires offer a harmonious blend of cultural richness, historical significance, and natural beauty, making it a sought-after destination in the Northeast U.S.

What is the best time to visit the Berkshires?

The Berkshires are a year-round destination, with each season offering its own unique charm. Summer is perfect for outdoor activities like hiking and boating, while fall offers stunning foliage. Winter is great for skiing and snowboarding, and spring brings beautiful blooms.

How do I get to the Berkshires?

The Berkshires are easily accessible by car from major cities like Boston and New York. There are also bus services from these cities. The closest airports are Albany International Airport in New York and Bradley International Airport in Connecticut.

Fall in the Berkshires is one of the coolest things to do throughout the year
Fall in the Berkshires is one of the coolest things to do throughout the year

Why do people vacation in the Berkshires?

People vacation in the Berkshires for many reasons, drawing from its unique attractions:

  1. Natural Splendor: The Berkshires is a haven of scenic beauty, characterized by its verdant rolling hills, dense forests, sparkling lakes, and vibrant fall foliage. The serene landscapes provide an idyllic setting for relaxation and rejuvenation.
  2. Cultural Retreat: Renowned for its arts scene, the region offers an array of cultural experiences, from the world-class performances at Tanglewood and dance showcases at Jacob’s Pillow to the plays at the Williamstown Theatre Festival.
  3. Artistic Exploration: Institutions like the Massachusetts Museum of Contemporary Art (MASS MoCA) and the Norman Rockwell Museum cater to art enthusiasts, presenting both contemporary art and classic American illustrations.
  4. Historical Insights: The Berkshires brims with history. Sites like Edith Wharton’s former home, The Mount, give visitors a glimpse into the past and the literary legends that once graced the region.

No matter what vacation activities interest you, the Berkshires will take your breath away. It’s truly a place where one can find both inspiration and tranquility, making it a favored vacation spot for many.

What outdoor activities are available in the Berkshires?

The Berkshires offer a wide range of outdoor activities, including hiking, biking, boating, fishing, skiing, and snowboarding. There are also several beautiful parks and nature reserves for wildlife viewing and picnicking.

How many days do you need in Berkshires?

The number of days you should spend in the Berkshires depends on what you want to experience. However, for a well-rounded trip, a 3 to 4-day itinerary is ideal.

  • Day 1: Explore the cultural and artistic sites. Visit the Massachusetts Museum of Contemporary Art (MASS MoCA) and the Norman Rockwell Museum. If time allows, catch an evening performance at Tanglewood or another local venue.
  • Day 2: Dive into the region’s history. Spend the morning at The Mount, Edith Wharton’s former home, and the afternoon exploring historic sites or strolling through charming towns like Lenox, Stockbridge, or Great Barrington.
  • Day 3: Embrace the outdoors. Hike a portion of the Appalachian Trail or another popular trail, kayak on a local lake, or, depending on the season, ski or snowboard. The evening could be perfect for a farm-to-table dining experience.
  • Day 4: Dedicate to relaxation and shopping. Perhaps spend a day at a spa like Canyon Ranch, or explore local shops, galleries, and markets. If you’re there during a special event or festival, this day could be allocated to that experience.

Of course, this is just a sample New England itinerary, and the Berkshires has plenty more to offer. If you’re a dedicated arts, nature, or history enthusiast, you might wish to allocate more time to delve deeper into those particular areas.

Are the Berkshires family-friendly?

Absolutely! The Berkshires have plenty of family-friendly attractions, including museums, parks, and outdoor activities. Whether your family loves adventure, art, history, or nature, you’ll find something to enjoy in the Berkshires.

What cultural attractions are there in the Berkshires?

The Berkshires are known for their rich cultural scene, with numerous museums, art galleries, and performing arts venues. Highlights include the Norman Rockwell Museum, Mass MoCA, The Clark Art Institute, and the Berkshire Theatre Group.

The Berkshires: Your Next Adventure Awaits

Whether you’re hiking the Appalachian Trail, exploring the galleries of Mass MoCA, or enjoying a peaceful day by Pontoosuc Lake, you’ll find that the Berkshires have a way of leaving an indelible mark on your heart. Each corner of this region offers a new discovery, a new story, and a new adventure.

From the vibrant fall foliage to the serene snowscapes of winter, from the lush greenery of spring to the warm, sunny days of summer, the Berkshires are a feast for the senses all year round.

So why wait? Pack your bags, set your GPS, and embark on an unforgettable journey to the Berkshires. If you’re planning a weekend getaway or a longer vacation, this guide to the best things to do in the Berkshires will help you make the most of your trip. From the moment you arrive, you’ll understand why the Berkshires are a beloved destination for so many.

In the Berkshires, every day brings a new adventure. It is a place for a new discovery and a new opportunity to fall in love with this enchanting region. So, come and experience the best places to visit in the Berkshires for yourself. We promise you won’t be disappointed.

The top things to do in the Berkshires for all types of travelers
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