11 Top-Rated Things to Do in The Berkshires

Author Meagan Drillinger spent much of 2021 driving and exploring the many towns of the Berkshires.

When the streets of Boston and New York City are sweltering in the summer, residents ditch the concrete jungles and make their way to the undulating hills, lush forests, and beautiful resorts of The Berkshires. The area is a popular weekend getaway from Boston.

Located in western Massachusetts, The Berkshires are a collection of New England towns known for their bucolic environment, abundance of things to do, and centuries of history.

When looking for places to visit in The Berkshires, what you’ll find are plenty of museums, historic locations, and miles upon miles of wilderness.

Berkshire County is made up of two cities: Pittsfield and North Adams. Beyond these two cities are 30 towns in an area that spans nearly 950 square miles. Less than 10 percent of The Berkshires is developed—the rest sits shrouded in wilderness or veined with hiking, biking, and ski trails.

In summer, the fields turn brilliant green, cafés spill onto the sidewalk, and the air comes alive with live music and dance performances. Come winter, the world is hushed and washed in white, as snow coats the slopes of the mountains, including Mount Greylock, which is the highest peak in Massachusetts.

No matter the time of year, visitors will always find rewarding places and things to do in The Berkshires.

1. See a Performance at Tanglewood

Open since the 1930s, Tanglewood is an open-air music pavilion and the summer home of the Boston Symphony Orchestra. Each summer, thousands of visitors flock to the stage to soak up diverse programs of classical, jazz, contemporary, and pop music.

The estate sits between the towns of Lenox and Stockbridge, two of Massachusetts’ most beautiful small towns, and is a favorite for both residents and visitors.

While the main structure has remained largely unchanged since the inauguration nearly 100 years ago, the grounds now have indoor facilities and restaurants, which have allowed it to become more of a year-round entertainment facility.

Still, the summer is the most vibrant, when the grounds are humming with patrons, many of whom bring lawn chairs, blankets, and picnics to enjoy an evening of music in the warm weather.

Address: 297 West Street, Lenox, Massachusetts

2. Jacob’s Pillow

The Berkshires are a haven of culture, as you’ll soon discover. In addition to the music at Tanglewood, lovers of dance come to experience Jacob’s Pillow.

The 220-acre National Historic Landmark, and winner of the National Medal of Arts, is home to America’s longest-running international dance festival.

More than 50 dance companies and 500 free performances and events take place every year. It is also a world-renowned dance training center for performers.

Festival season typically runs through the summer, when visitors can experience ballet, contemporary dance, tap, as well as flamenco, hip hop, traditional Korean dance, musical theater, and so much more.

Address: 358 George Carter Road, Becket, Massachusetts

3. Experience Nature

The Berkshires region, while known for its restaurants, art, and excellent resorts and hotels, is still mostly undeveloped.

In fact, about 93 percent of the Berkshire region is undeveloped—and much of that has been protected in parks or reserves. Being outdoors in The Berkshires, in any season, is a good time, and the destination has plenty of opportunities to experience nature.

Monument Mountain, for example, is a popular hike in the Great Barrington portion of The Berkshires. The summit sits at 1,642 feet and offers visitors 360-degree views of the Housatonic River Valley. More than 20,000 hikers come to explore the boulders and cliffs of Monument Mountain every year.

Then there is Mount Greylock, which is the highest peak in Massachusetts at 3,491 feet. On a clear day, hikers can see as far as 90 miles away. The mountain is veined with trails of all levels and lengths, and most end up at the summit, where the views are breathtaking.

Tip: A café at the top of the summit has tasty sandwiches and salads, as well as picnic benches for enjoying the views.

For plummeting cascades, Bash Bish Falls State Park is the stop. It is the highest single-drop waterfall in the entire state of Massachusetts. It shares the border with Mt. Washington State Forest as well as New York’s Taconic State Park.

Those wanting something a little more leisurely and less intense can visit the Berkshire Botanical Garden. The garden was established in 1934 and spreads over 24 acres in Stockbridge. It is open year-round for classes and lectures, but visitors are in for a real treat in the spring and summer when the gardens are in full bloom.

The Berkshires are also home to several lakes, like Lake Onota, as well as the Audubon Society’s Pleasant Valley Wildlife Sanctuary, and the Pittsfield State Forest.

4. Visit Museums

But back to the culture—because The Berkshires has a lot of it. Museums are among the most popular tourist attractions in The Berkshires, and you’ll have your pick.

The Clark Art Institute (225 South Street, Williamstown), for example, is often considered to be the best in the region. Opened in 1955, the Clark combines a public art museum along with research and academic programs and an art history library.

The permanent collection includes European and American paintings, sculpture, prints, drawings, and photographs, which range from the Renaissance to the early 1900s.

The Manton Collection of British Art, for example, has more than 300 paintings and drawings, while the American Decorative Arts Galleries have more than 340 objects of American silver. Rotating exhibitions take place throughout the year, as well.

For modern art, Mass MoCA (1040 Mass MoCA Way, North Adams), or the Massachusetts Museum of Contemporary Art, is a sprawling space of galleries with a collection of indoor and outdoor performing arts spaces. It’s a center for music, sculpture, film, dance, theater, and more. The entire complex has more than 250,000 square feet of open space, and hosts 75 performances year-round.

Did you know that Norman Rockwell lived in The Berkshires for the final 25 years of his life? In fact, The Berkshires is the place to see the world’s largest collection of Rockwell’s work.

The Norman Rockwell Museum (9 Glendale Road, Stockbridge) has nearly 1,000 original paintings and drawings. His Stockbridge studio was also moved to the museum site.

And if it’s history you’re interested in, the Herman Melville Arrowhead Museum (780 Holmes Road, Pittsfield) tells the story of the famed author, who lived in the restored house from 1850 to 1863. Today the house is dedicated to the history of Berkshire County and the historic Arrowhead farm.

5. Go Skiing

When it comes to East Coast skiing, it’s tough to do better than The Berkshires. Part of the Appalachian Mountain range, the summits of Berkshire county rise more than 2,000 feet, making them a favorite ski destination among East Coasters.

While the peaks probably can’t give the ski regions of Utah or Colorado a run for their money, they certainly do provide ample opportunity for skiers in the northeast.

Among the ski areas in The Berkshires, a few stand out above the rest. Jiminy Peak Mountain Resort, for example, is one of the largest ski and snowboard resort towns in New England. The summit reaches 2,380 feet, but this is a great mountain for all lives.

More than half the runs are for beginners, while 30 percent are for intermediate. Advanced runs cover 13 percent of the mountain. Jiminy Peak has 45 runs and three terrain parks.

Ski Butternut is one of the top ski resorts on the east coast, especially for families. It offers 100 skiable acres, with 20 percent of trails for beginners, 60 percent for intermediate, and 20 percent for advanced. It has 10 lifts, and all trails are equipped with snowmaking capabilities.

Also in The Berkshires, Bousquet Mountain has been welcoming skiers since the 1930s. The mountain has a peak elevation of 1,818 feet, and the ski area spans 200 acres. It has 24 trails, two lifts, two magic carpets, and one terrain park.

Catamount Mountain Resort is yet another ski area in the region, with 13 beginner trials, 16 intermediate trails, and seven advanced trails. But Catamount also makes a great destination in the summer, thanks to the 2019 addition of the Catamount Zip Tour, which features one of the longest ziplines in the United States at more than 5,500 feet.

6. Get Active at the Adventure Parks

The Berkshires are action-packed in the winter, but there are plenty of top things to do in The Berkshires in the summer, as well. Adventure parks, for one, make for an adrenaline-fueled day for the whole family.

Let’s start with Ramblewild in Lanesborough, a tree-to-tree adventure park in Feronia Forest. This aerial park has eight aerial obstacle courses that are perched high above the ground in the forest canopy.

Intrepid travelers can wander through the trees at this lofty height, experience the courses’ many different elements, from high wires and zip lines to rope ladders, cargo nets, suspended bridges, and more.

Catamount’s ski area makes the most out of the non-ski season with an aerial adventure park, as well. The Catamount Aerial Adventure Park has 12 aerial trails that wind their way through the lush forest. Cross bridges, climb ladders, and zoom down zip lines all in the forested park at the base of the mountain.

7. The Mount, Edith Wharton’s Home

If you’ve ever enjoyed the stories of Edith Wharton, such as The Age of Innocence, Ethan Frome, and The House of Mirth, you will likely love a visit to her home and estate, The Mount, located in The Berkshires.

Wharton was a trailblazer for women. She wrote 40 books in 40 years and was the first woman awarded the Pulitzer Prize, among many other accolades.

She bought 113 acres of land in Lenox, Massachusetts in 1901, and it was here that she designed and built The Mount. While she only lived here for a decade, it was within The Mount that she composed some of her greatest work.

Today The Mount and its grounds pay homage to her life and her work. Wander the re-imagined, historic rooms that tell the stories of the lives of everyone who lived at The Mount, but Wharton in particular. Visitors can also wander the gardens and the stable, in addition to the main house.

Address: 2 Plunkett Street, Lenox, Massachusetts

8. Naumkeag

Speaking of historic homes, while in The Berkshires, you may want to hop over to Stockbridge to visit Naumkeag.

This historic home once belonged to Joseph Choate, a New York attorney, and his wife, Caroline. The magnificent 44-room home sits on 48 acres and is considered to be an architectural marvel. In fact, it is now a National Historic Landmark.

Visitors can wander the rooms of the house, as well as stroll its impressive grounds, which are heralded for their vibrant, expertly manicured gardens.

A highlight are the Blue Steps, a series of blue pools, bordered on either side by four flights of stairs and beautiful birch trees. Discover the Rose Garden, Evergreen Garden, Chinese Garden, and much more.

Address: 5 Prospect Hill Road, Stockbridge, Massachusetts

9. Hancock Shaker Village

One of the most interesting religious movements in America, the Shakers are a religious order that believe in peace, celibacy, and communal living. They arrived in America from England in 1774 and created a name for themselves thanks to their art, craftsmanship, music, agriculture, and more.

Hancock Shaker Village is the third of 19 Shaker villages that were established in the United States. At its peak in the 1840s, the village had more than 3,000 acres and 300 members. Today visitors can step back in time and learn about the Shakers of The Berkshires at Hancock Shaker Village.

The compound sits on 750 acres and is open as a living-history museum, with 20 Shaker buildings, furniture, activities, hiking trails, and a working farm. The village has more than 22,000 artifacts and is considered to be the most comprehensive Shaker site in the world.

10. Ventfort Hall Mansion and Gilded Age Museum

The historic homes of The Berkshires are more than impressive. But none is as fabulous as Ventfort Hall Mansion and Gilded Age Museum, an eerie, striking Jacobean Revival mansion that was built in the late 19th century for Sarah Morgan (the sister of the one and only J.P. Morgan).

It’s no surprise that this Gilded Age treasure is on the National Register of Historic Places. But it wasn’t always that way. In 1997, Ventfort Hall had fallen into such disrepair that it was considered among the 11 most endangered properties in Massachusetts.

After a meticulous restoration, it was rebuilt to its former grandeur, with a reconstructed grand staircase, gallery, and imposing Great Hall, which stands at two stories.

Today the mansion, which houses the Museum of the Gilded Age, is available for self-guided tours.

Address: 104 Walker Street, Lenox, Massachusetts

11. Peep the Fall Leaves

The northeastern United States has some of the best leaf-peeping in the world, and the Berkshires is at the top of that list.

The many scenic drives that weave across the Berkshires region are blessed with backdrops of rich, vibrant foliage. From late September through mid-October, the trees of the Berkshires practically explode with yellows, oranges, and reds.

One of the best drives to experience the fall foliage in the Berkshires is along Route 2, which has spectacular views over the treetops from a higher elevation. The carpet of autumnal hues that stretches out over the valley is simply breathtaking.

Another place to marvel at the fiery foliage is from the top of Mount Greylock in Adams. Visitors can either take a hike up the mountain (some hiking experience is required for this hike), or you can drive to the top of the mountain.

No matter which you opt for, you will be rewarded with 360-degree views from the highest peak in Massachusetts. Some days you can see as far as Vermont, New York, and Connecticut, which means you’ve got the bucket-list view for leaf peepers in New England.

Closer to Lee, the best foliage can be seen along a central loop that includes the towns of Becket, Hinsdale, Dalton, Pittsfield, West Stockbridge, and Lenox. You can also try the Jacob’s Ladder Scenic Byway that runs along Route 20 from Lee to Russell.

Map of the Berkshires – Top-Rated Things to Do