The Best Things to Do in the Berkshires: A Complete Travel Guide

Location: The Berkshires

When people talk about travel in Massachusetts, the spotlight usually lands on Boston or Cape Cod. But if you skip the Berkshires, you are missing one of the most beautiful regions in the entire state. Rolling mountains, charming towns, historic estates, and a thriving arts scene make this corner of western Massachusetts incredibly special.

If you are searching for things to do in the Berkshires, this guide will help you plan the perfect trip.

Personally, fall is my favorite time to visit the Berkshires. The crisp mountain air is perfect for hiking, the forests glow with vibrant foliage, and every small town feels straight out of a postcard. But no matter when you visit, there are countless things to do in the Berkshires for couples, families, and outdoor lovers alike.

What surprised me most during our trip was how family friendly the attractions were. I was nervous bringing my kids into historic Gilded Age mansions, but the museums and historic sites welcomed children and made the experience engaging for all ages.

We had such an amazing time exploring that we kept extending our trip. In the end, we spent four action packed days discovering some of the very best things to do in the Berkshires.

To help you plan your own adventure, I organized this guide by town, starting in the southern Berkshires and working north. This route makes it easy to follow along if you are planning a road trip through the region.

Table of Contents

The Best Things to Do in the Berkshires

1. Hike to Bash Bish Waterfall (Mt. Washington, MA)

One of the most iconic things to do in the Berkshires is visiting Bash Bish Falls, the tallest waterfall in Massachusetts. A short and scenic hike leads to the dramatic 60 foot cascade surrounded by forested cliffs.

It is important to note that there are two entrances to the falls. Because the park sits directly on the Massachusetts and New York state line, you can access the trail from either state. The Massachusetts side offers a shorter but steeper hike, while the New York entrance is longer but much more gradual.

For families, I recommend using the New York trailhead. The walk is easier and still delivers the same breathtaking view of the waterfall at the end.

2. Naumkeag (Stockbridge, MA)

The Berkshires are filled with Gilded Age estates built by wealthy New Yorkers who escaped the city for their summer “cottages.” Naumkeag is one of the most impressive. The 44 room mansion is now cared for by The Trustees of Reservations and is open to visitors.

While touring the house is interesting, the real highlight is the gardens. My kids loved wandering through the manicured terraces and rows of trees, while we admired the sweeping mountain views dotted with grazing cows in the distance.

3. Berkshire Botanical Gardens (Stockbridge, MA)

We had not planned to visit, but since it sits right across the street from Naumkeag, we decided to stop in. I am so glad we did because it ended up being one of our favorite spots. There is a wonderful children’s garden with a playhouse, chicken coop, and fairy garden, along with an outdoor classroom where crafts and activities take place. My kids could have stayed there all afternoon.

Beyond the children’s area, we wandered along the trails through different garden spaces. Unlike many botanical gardens that keep visitors strictly on the paths, this one encourages exploration. My kids climbed trees, built little forts, and discovered shady hideaways. It felt like a place where families were truly invited to enjoy the grounds rather than just admire them from a distance.

4. Turn Park (Stockbridge, MA)

By this point in the day we were ready for lunch, so we grabbed sandwiches from a deli in the center of town and headed to Turn Park Art Space for a picnic.

Turn Park is a fascinating place that blends art, nature, and history. The 16 acre sculpture park sits on the site of a former marble quarry and features contemporary sculptures, art installations, and scenic walking paths set throughout the landscape. It is a beautiful place to wander, stretch your legs, and enjoy the surroundings.

If you need a little afternoon boost, stop by Depot 6 down the street, which is known for having some of the best coffee in town.

5. Norman Rockwell Museum (Stockbridge, MA)

Norman Rockwell chose to live in Stockbridge because he believed it represented the best of small town America. Visiting the museum was incredible. Standing in front of an original Rockwell painting valued at millions of dollars was surreal. We also saw the studio where he rode his bike each day to create the illustrations that would eventually become iconic pieces of American storytelling. It is inspiring for children to see what hard work and imagination can do.

I worried that the museum would not appreciate having children there and when a docent quietly walked over to us, I thought for sure we would be getting scolded, but she just wanted to tell my kids a story about the painting he was looking at. I thought that was pretty cool.

6. Hike up to Laura’s Tower (Stockbridge, MA)

The Ice Glen Trail is one of my favorite hikes in New England. Stone steps wind through a cool, mossy forest that honestly looks like something straight out of FernGully. The trail eventually leads up to Laura’s Tower, where you are rewarded with beautiful views overlooking the Berkshires.

The trail can be a bit tricky to follow in places, so it helps to use an app like AllTrails for navigation. There are also two different entrances to the hike. We drove down Ice Glen Road and parked in a small pull off on the left, then followed the signs from there. Bring bug spray and good walking shoes, and note that leashed dogs are welcome on the trail.

7. Olivia’s Overlook (West Stockbridge, MA)

We discovered this scenic overlook in West Stockbridge by chance, and the view is truly spectacular, especially during fall foliage season. It is a quick stop but absolutely worth pulling over for the sweeping views of the Berkshires.

8. Have a historic stay at the Red Lion Inn (Stockbridge, MA)

The Red Lion Inn is one of New England’s classic historic inns and has welcomed notable guests over the years, including Nathaniel Hawthorne and Henry Wadsworth Longfellow. Guests can enjoy a meal on the charming front porch or relax with a swim in the slate-lined pool. We had a wonderful stay at this grand old hotel and loved its timeless character.

9. Housatonic River Walk (Great Barrington, MA)

The River Walk follows the west bank of the Housatonic River between Cottage Street and Bridge Street. We only spent a short time here, but it was a peaceful place to stroll along the water and learn about Great Barrington native W.E.B. Du Bois, an early leader in the Civil Rights Movement. His deep connection to the Housatonic River helped inspire his advocacy for protecting rivers around the world.

Rescue the Housatonic and clean it as we have never in all the years thought before of cleaning it… restore its ancient beauty; making it the center of a town, of a valley, and perhaps-who knows? of a new measure of civilized life.
–W.E.B. Du Bois, 1930

10. Shopping on Main Street (Great Barrington, MA)

Downtown Great Barrington is a lovely place to wander, browse, and shop. There are several charming toy stores that kids will adore. Tom’s Toys was their clear favorite, while I loved Matrushka Toys for its wonderful selection of books. If you are craving something sweet, be sure to stop by Robin’s Candy for a treat.

11. Eat at the Barrington Courtyard (Great Barrington, MA)

We had planned to grab pizza at Baba Louie’s, a local favorite, but it happened to be closed during our visit. Instead, we wandered down a colorful alleyway filled with vibrant street art and discovered the Barrington Courtyard.

This outdoor dining space brings several local restaurants together in one lively spot. You can order from different vendors while enjoying live music and a relaxed atmosphere. With options ranging from Moroccan to Mexican cuisine, there is something for everyone. The courtyard is open seasonally.

12. Soco Creamery (Great Barrington, MA)

Soco Creamery, often voted the best ice cream in Massachusetts, serves all natural, small batch ice cream that is absolutely worth the stop. I ordered the espresso cookie flavor and it was incredible.

The shop sits on Railroad Street, where this section of the road is closed to most traffic. Kids can run around safely while families relax and sometimes enjoy live music nearby. It had such a lively, welcoming atmosphere that I instantly felt like I had found my happy place.

13. The Mount (Lenox, MA)

Here is our funny story about visiting The Mount. We arrived and immediately started admiring the beautiful building in front of us when a woman kindly pointed out that we were actually looking at the horse stables. We still laugh about that.

To reach the main house, you follow a winding driveway through the woods. And if the stables impressed us, Edith Wharton’s actual home was even more stunning when we finally reached it.

Edith Wharton was a celebrated author at a time when women were largely expected to focus on marriage and family rather than careers. As we toured the house, the kids were especially fascinated by the ghost stories connected to the property.

Before leaving, don’t miss having tea on the veranda and taking time to wander through the beautifully manicured gardens surrounding the estate.

14. Pleasant Valley Wildlife Sanctuary (Lenox, MA)

Pleasant Valley Wildlife Sanctuary spans more than 1,000 acres in the Berkshires and offers a network of trails that wind through forests, meadows, wetlands, and along the slopes of Lenox Mountain. With routes ranging from easy walks to more challenging hikes, it is a wonderful place to explore the natural beauty of the Berkshires. The sanctuary is open daily from 9 am to 4 pm.

15. Tanglewood (Lenox, MA)

Tanglewood is one of the most iconic cultural destinations in the Berkshires and is best known as the summer home of the Boston Symphony Orchestra. Throughout the season, the venue hosts a wide range of performances, from classical concerts to contemporary artists, attracting music lovers from around the world.

The setting is just as memorable as the music. With sweeping lawns and beautiful mountain views, many visitors bring picnic blankets and enjoy the performance outdoors, making Tanglewood a perfect mix of world class music and the natural beauty of the Berkshires.

16. Chocolate Springs (Lenox, MA)

Chocolate Springs quickly became one of our favorite stops. The European style chocolates are beautifully crafted and look like little works of art. I ordered a salted caramel truffle and it was so good that I went right back for another. My kids loved the chocolate dipped marshmallows.

17. Hancock Shaker Village (Pittsfield, MA)

This living history museum was another highlight of our visit. The Shakers were a fascinating religious community whose name came from the trembling and shaking that occurred during their energetic worship services. Led by a woman, the group came from England in search of religious freedom.

What began as a small group of eight eventually grew to nearly 300 members living at Hancock Shaker Village. The Shakers believed that work was a form of worship, spending their days farming the land and crafting beautifully made goods. They became especially well known for their elegant and carefully designed furniture.

My kids especially loved visiting the animals in the village’s iconic round barn.

18. Visit the house where Moby Dick was written (Pittsfield, MA)

Arrowhead, also known as the Herman Melville House, is a historic home in Pittsfield where the author lived while writing some of his most important works. Melville drew inspiration from the landscapes of the Berkshires, which surrounded the property.

His famous novel Moby-Dick was published in 1851 but was not widely appreciated at the time. It was not until the 20th century that the book was recognized as one of the great American novels.

Today, visitors can tour the home and learn about Melville’s life and writing. Guided tours run from 10 am to 3 pm, beginning at the top of each hour and lasting about an hour. The museum is open Thursday through Monday and closed on Tuesdays and Wednesdays.

19. Mass Moca (North Adams, MA)

I will admit that I am not usually a big art museum person, but MASS MoCA completely surprised me. This contemporary art museum is what really put North Adams on the map. The museum is housed in a massive former industrial complex, and it feels like the galleries go on forever.

There is always something unusual and thought provoking around every corner. Kids will especially enjoy Kidspace, where they can turn their inspiration into their own creative projects.

20. Natural Bridge State Park (North Adams, MA)

Natural Bridge State Park is home to the only natural white marble arch in North America. The formation was carved over millions of years as glaciers slowly shaped the bedrock, creating a dramatic arch and striking rock formations.

Visitors can walk along the pathways for a closer look at the marble cliffs and the natural bridge itself. Nearby, a peaceful birch lined meadow sits in a former marble quarry and makes a beautiful spot to relax or enjoy a picnic.

21. Drive to the top of Mt. Greylock (North Adams, MA)

From May through November, visitors can drive to the summit of Mount Greylock, the highest point in Massachusetts. At 3,491 feet above sea level, the views stretch for miles, and on a clear day you can see up to 90 miles across the surrounding mountains.

When we visited, we had a clear view of Mount Wachusett and even Stratton Mountain in Vermont. At the summit, you can climb the Veterans War Memorial Tower for an even better vantage point or stop by Bascom Lodge for a bite to eat.

Susan B. Anthony was a pioneering women’s rights activist and a leading figure in the fight for women’s suffrage. The museum explores the family and regional influences that shaped her early life and helped inspire her lifelong work for equality.

23. The Clark (Williamstown, MA)

The Clark is a unique institution that combines a world class art museum with an academic research center. While the museum is quite sophisticated, it was still very welcoming for families. My kids were given an activity pack with an art pad, pencil, and a scavenger hunt card that encouraged them to look for specific works throughout the galleries.

The grounds outside are just as impressive as the museum itself. With scenic trails, open lawns, and outdoor sculptures, it is easy to spend hours exploring the landscape. The grounds are free to visit and open year round, making them a wonderful place to wander and soak in the beauty of the Berkshires.

When I think of the Berkshires, I picture a place where creativity thrives. It is the kind of place that naturally sparks inspiration. If you are interested in more theater and dance, be sure to check out Jacob’s Pillow or Shakespeare & Company.

I hope this guide to the best things to do in the Berkshires helps you plan your visit. The Berkshires offer the perfect mix of outdoor adventure, culture, and charming small towns.

Whether you come for the hiking trails, historic estates, art museums, or great food, there are so many memorable things to do in the Berkshires that you will likely find yourself planning a return trip before you even leave.