12 Fun Things to Do in Stockbridge, MA

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Join me on a visit to Stockbridge, MA: this is the heart of the Berkshires, where the Housatonic River meets the Appalachian Trail. For more than 300 years, Stockbridge has been a popular destination for visitors and a home to artists, writers, intellectuals — and the occasional travel blogger!

Stockbridge is one of my favorite towns in the Berkshires — because it’s exactly what your mind pictures when you dream of small town New England. So much of Stockbridge is straight out of a postcard. And as a Massachusetts native who has traveled all over her home state, I can’t believe it took me until my thirties to finally visit!

Stockbridge was originally inhabited by the Mohican Indigenous tribe. In 1739, English settlers arrived and purchased the land, establishing Stockbridge Township. In the 19th century, Stockbridge became a popular summer destination for wealthy New Yorkers and Bostonians who were drawn to its beautiful scenery, cooler climate, and cultural attractions.

Today, Stockbridge is an essential stop for any weekend Berkshires getaway. The town is home to some of the best museums in the region, art galleries, theaters, shops and restaurants. The town is also surrounded by beautiful scenery, with hiking trails, waterfalls, and a beautiful lake. 

But what I love most about Stockbridge is driving through the quiet streets and admiring all the old homes tucked into the hills. It looks straight out of a Norman Rockwell painting. Which makes sense because Norman Rockwell called Stockbridge home for many years! He even has a museum dedicated to his work here in Stockbridge.

Whether you’re coming for a theater-filled summer getaway or the springtime flower festivals, a cozy winter escape or the best of fall foliage, Stockbridge is a year-round destination you’re going to love.

(Planning a trip to the Berkshires? Be sure to check out the Best Things to Do in the Berkshires and my guide to the Towns of the Berkshires.)

This post was published in January 2024 and co-written by Adventurous Kate and Susan Stephens.

An old-fashioned yellow house with dark green shutters and a large porch set among trees at the end of a driveway in Stockbridge, Massachusetts.

Things to Do in Stockbridge, MA

Explore Main Street and Downtown Stockbridge

The heart of Stockbridge lies in its historic downtown area, filled with wonderful art galleries, specialty shops, cozy cafes, and town offices. On Main Street, manicured lawns are interspersed with the quiet bustle of small-town shops and eateries — many of them housed in historic buildings restored to their past glory.

Stockbridge is home to a vibrant community of local businesses that offer a unique shopping experience in the downtown area. From exquisite glass art to handcrafted jewelry to locally-made goods, you’ll find plenty of treasures to take home. If you’re looking for a souvenir from Stockbridge, I’d recommend stocking up here.

The Schantz Gallery, in particular, is a worthwhile stop, as well as the legendary Red Lion Inn (more on these later in this post!). Take a stroll down Main Street and you’ll encounter friendly locals who are always happy to share their favorite spots. 

And if you’re up for a refreshment, I love the coffees on offer at Stockbridge Coffee & Tea!

Interior of the Norman Rockwell Museum, paintings on walls. You see his famous painting of Ruby Bridges walking to school on the left.

Dive into the Norman Rockwell Museum

The Berkshires are full of excellent art museums — but the Norman Rockwell Museum is probably my favorite. The museum welcomes visitors to a journey through American history as seen through the eyes of a legendary artist.

From whimsical portrayals of Main Street to profound depictions of a changing world, each artwork is a testament to Rockwell’s ability to capture the essence of American life. The museum is home to the world’s largest collection of Rockwell’s original artwork, as well as a number of other exhibits related to his life and work.

A lot of people use “Norman Rockwell” as a synonym for a throwback to old-fashioned life in the 50s. But what I think some people miss is that Rockwell was a hardcore progressive who used his art as a medium of protest. His portrait of Ruby Bridges is one of the most famous works in the museum.

Each room of the museum opens a new chapter, allowing visitors to experience the rich American history preserved in Rockwell’s works. And don’t miss the little red cabin in the back where he lived.

Admission to the museum is $20 for adults, $18 for seniors, and $10 for college students with a valid ID. Children under 18 can visit free of charge. 

A brick mansion with an immaculate stone wall in front of it.

Explore Naumkeag

The Berkshires are full of gorgeous Gilded Age mansions you can visit, and Naumkeag is one of the jewels of Stockbridge, MA. The main mansion, built in the late 19th century, showcases the opulence of the Gilded Age, with every room boasting intricate detailing and ornate decor.

The gardens are a spectacle all their own, ranging from the vibrant Afternoon Garden to the tranquil Rose Garden, and culminating in the famous Blue Steps. I highly recommend visiting in spring or summer if you can to experience the flowers at their best!

Naumkeag originally served as the summer retreat of the Choate family. The estate’s name, Naumkeag, is derived from the Native American term for “fishing-place.” The mansion is perched on a hill, and from the terrace you can enjoy views of the Berkshire Mountains.

The estate frequently hosts special programs and events. Naumkeag is open to public during the peak months of spring through fall, and during the winter is only open for events. Check their website for current openings. I recommend pre-registering your visit in advance.

Admission to the grounds and interior is $20 for adults, $15 for seniors and students with ID, and $5 for children ages 3–12.

A marble statue of a naked woman leaning back, arching her back, an angel above her.
Daniel Chester French’s studio at Chesterwood, Stockbridge MA

Stroll through Chesterwood

Chesterwood is another beautiful estate in the Berkshires — a must-visit, in my opinion. This property was once the summer home and studio of renowned American sculptor Daniel Chester French, who created the iconic Lincoln Memorial statue in Washington, DC. The estate houses French’s house, garden, and studio, where he spent 36 summers crafting timeless pieces of art.

I didn’t know much about French before visiting — other than the Lincoln Memorial, of course — but enjoyed this deep dive into his life and work. The artist’s residence is preserved to reflect his era, showcasing his personal belongings, art collections, and furniture.

The studio, on the other hand, displays a multitude of his sculptures, allowing visitors a behind-the-scenes glimpse into his creative process. The formal gardens are designed by French himself, featuring magnificent views of the Berkshire Hills, offering a tranquil retreat for nature lovers.

Chesterwood is open to the public from late May through Columbus Day. General admission includes a tour of the home and studio and is $20 for adults, $18 for seniors, $15 for military, $10 for students with ID, and free for children under 13. Admission for the grounds only is $10. 

A botanical garden with a small plot covered with a variety of different flowers.
Late spring brings cherry blossoms in the Berkshire Botanical Garden!

Wander the Berkshire Botanical Garden

The Berkshire Botanical Garden is a perfect outdoor getaway in between your museum-hopping. This 15-acre garden showcases more than 3,000 species of plants and is a sight to behold in any season. Take a leisurely stroll or join one of their guided tours to learn more about the beautiful flora on display.

The garden dates back to 1934, making it one of the oldest display gardens in the Northeast. The Botanical Garden also puts on all kinds of events, from yoga and tai chi classes among the flowers to workshops, receptions, and even classes in watercolors, birding, and chainsaw maintenance (seriously).

The garden is open for visitors from late April through October, and for special events on select winter dates. Admission is $18 for general admission, $16 for seniors, and free for children under 12. Admission is pay-as-you-wish on Tuesdays.

A lake covered with gentle mist on an early fall morning, a partly cloudy sky ahead.
A gorgeous morning at Lake Mahkeenac, via Shutterstock.

Relax at Lake Mahkeenac

Located just four miles north of town, this is a place where you can kick back and enjoy the beauty of nature. Lake Mahkeenac, also known as Stockbridge Bowl, is surrounded by forested hills and covered with hiking trails.

When you’re ready to get in the water, you can choose from a variety of activities. Swimming, kayaking, and boating are all popular options. And if you’re feeling adventurous, you can even try waterskiing! The Stockbridge Town Beach is great for swimming, with restrooms, picnic tables, and lifeguards during the summer months.

Fishing is popular at the lake, with 13 species to be caught (though do know that a fishing license is required). Public boat access is available on the northwestern shore. To get to Lake Mahkeenac, take Route 102 from Stockbridge. Turn right onto Route 183 and follow it until you reach the lake.

A man and woman on stage in 1920s clothing, looking very serious.
Theater performance, via DepositPhotos

Experience the Berkshire Theatre Group

The Berkshires embrace the arts year-round, but especially during the summer months, when theatrical performances take place across the region! Berkshire Theater Group, holds a special place in the hearts of the local community. Established in 1928, it stands as one of the oldest professional performing arts organizations in New England.

As a theater-loving girl, let me tell you that there is SO much more to the theater group than Broadway. Some of my favorite performances have been in small theaters in random locations!

Their performances span a broad spectrum, from Shakespearean plays to modern musicals, and they are dedicated to nurturing the talents of both emerging and established artists. Attending a performance by the group is more than just an evening out; it’s an opportunity to engage with the community, to appreciate the talents of local artists, and to immerse oneself in the enduring culture of Western Massachusetts.

The group performs in two historic venues: the Unicorn Theatre in Stockbridge, an intimate theater nestled in the heart of the town; and the Colonial Theatre in nearby Pittsfield, a beautiful and grandiose structure dating back to 1903.

An old-fashioned in with a big porch, and a sign reading Red Lion Inn with a red lion on it.
Here’s a tip: those porch seats are priceless!

Enjoy a Drink at the Historic Red Lion Inn

Nestled in the heart of downtown, the Historic Red Lion Inn stands as a testament to time. For many frequent Stockbridge visitors, it’s the highlight of their stay!

Established in 1773, the inn has witnessed countless historical events, hosted notable figures. Today you too can stay overnight in the inn as a guest. I have and I’ve enjoyed it! But if you’re not staying here, you can pop by for a drink, a meal, or a quick exploration through the public areas.

One of the most intriguing aspects of the Red Lion Inn is its speakeasy, aptly named The Lion’s Den. During the Prohibition era, this clandestine establishment served as a haven for those seeking a taste of the forbidden. Inside, they found a lively atmosphere where libations flowed freely and jazz music filled the air. 

Beyond the speakeasy, the Red Lion Inn offers visitors a glimpse into the past with its meticulously preserved architecture. The inn oozes colonial charm with its wide-plank floors, exposed beams, and cozy fireplaces, and has been recognized as a National Historic Landmark.

I recommend grabbing one of the coveted rocking chairs on the porch to watch the comings and goings of people in downtown Stockbridge.

Appreciate Art at Schantz Galleries

Art enthusiasts won’t want to miss a visit to Schantz Galleries, known for its collection of museum-quality contemporary glass art. The gallery features works by established and emerging artists, both local and international, making it a must-visit for anyone interested in the art scene (or anyone who has binged Blown Away on Netflix — I did too!).

Upon entering the gallery, visitors are greeted by masterpieces sampling a dizzying array of techniques and interpretations in the world of glass sculpture. Using color, form, and texture, each artist explores light and space in amazing ways. 

If you are looking for a special item for your home or as a gift, the gallery staff are experts at helping you find the perfect art piece. Commissions are also possible from the many artists they represent. Be sure to visit their website for current installations and a list of renowned artists. 

A huge white mansion with lots of black shutters on a hill in the Berkshires.
Edith Wharton’s The Mount is a must-visit in Lenox, MA.

Visit Lenox

Located just ten minutes by car north of Stockbridge, Lenox is home to some of the most famous places to visit in the Berkshires. In fact, Lenox would also make a great base for exploring the Berkshires. I do feel that Lenox tends to cater to the wealthy a bit more than Stockbridge, but there’s still plenty to explore here.

Lenox is most famous for Tanglewood, the summer home of the Boston Symphony Orchestra, with plenty of concerts during the summer months; and Canyon Ranch, one of the most lauded spas in the world.

Some other notable places to visit are Ventfort Hall, a Gilded Age historic home with its architectural greatness, and Edith Wharton’s The Mount, the historic home of Pulitzer Prize-winning writer.

Those who enjoy nature should not pass up the Pleasant Valley Wildlife Sanctuary just outside town. Home to a gaggle of birdlife, its 1,000 acres are filled with natural habitat and plenty of hiking trails (including some that are wheelchair-accessible!).

See my full guide to Lenox here.

A large red brick building that used to be a furniture factory, with a boutique on the ground floor. In the foreground, a crosswalk painted rainbow colors.

Visit Great Barrington

Known as the “Brooklyn of the Berkshires,” Great Barrington has a fun, urban, youthful vibe.  Located in the south of the Berkshires, this makes for a great day trip from Stockbridge (and pairs well with a visit to nearby Bash Bish Falls or Sheffield).

Downtown Great Barrington is great for exploring on foot. Here you can stroll Main Street and go from trendy coffee shops to boutiques to the local dispensary without batting an eye.

Also downtown is the Housatonic Riverwalk, a lovely public path following the edge of the river, which makes the perfect place to take a break from shopping or to work off your leisurely lunch.

Then when you’re ready for natural landscapes, Great Barrington is surrounded by woods and mountains. Monument Mountain features one of the most beautiful hikes in the region, with three trails leading to its summit. They are all reasonable hikes at under three miles each! 

A downtown area with a Greek revival building with tall columns next to a brick building with an outdoor cafe.
Williamstown brings the cute factor.

Visit Williamstown and North Adams

These two towns are right next door to each other in the north of the Berkshires and make a great day trip from Stockbridge. North Adams is a former mill town turned artistic haven, where grittiness meats creativity. The most famous attraction in town is MASS MoCA (Massachusetts Museum of Contemporary Art), an outstanding collection of modern art where you could wander for hours.

Other attractions in North Adams include Natural Bridge State Park, which features the only natural white marble arch on the North American continent. Afterward, park your car at the North Adams YMCA and do an easy hike to Cascade Waterfall. 

Williamstown is just next door to the west and is a picturesque college town home to Williams College. Cute shops and eateries abound, mostly catering to the college crowd, but still a great place to spend a few hours. It is a nice contrast to North Adams, as it feels much smaller and well-manicured.

While in Williamstown, be sure to check out the Clark Institute, which houses one of the best Impressionism collections on the planet. I was shocked — it rivals collections in New York or Paris! If you’re here during summer, the Williamstown Theater Festival brings in the crowds. 

An outdoor restaurant built into what looks like a residential house with two stories and porches on the second floor.
Dining out in the Berkshires!

Tips for Visiting Stockbridge, MA

Here’s something you should know before visiting: phone signal in Stockbridge still isn’t great, even in 2024. I was surprised how often I didn’t have any signal and had to go find wifi somewhere.

(I think it’s because the town wants to preserve their historic heritage, so they do the minimum in coverage. The same reason why there’s no stoplight at the busy intersection of Main St. and Pine St., even though there really should be one.)

This isn’t a huge deal-breaker, but just something to keep in mind. More than once I was miffed when I got to my car, put in directions to my next destination on Google Maps, and was hit with “No service.” Get the directions on while you have wifi!

As for getting around Stockbridge, a car is best. Public transportation in the Berkshires is scant if it exists at all, there are cab companies but there is no Uber, and you’ll have a much easier time with your own wheels.

Even if you’re staying in Stockbridge the whole time, many of the sights like Chesterwood and the Norman Rockwell Museum are far from downtown and require a car to get there.

A small garden of tulips overlooking a mountain in the distance.
Tulip gardens in full bloom at Naumkeag in Stockbridge MA.

How Much Time to Spend in Stockbridge, MA

I think two days is a good amount of time for visiting Stockbridge. If you’re starting from Boston or nearby, I recommend staying for a minimum of two nights to enjoy the downtown, see several different museums and historic sites, and enjoy most of what the town has to offer.

If you’re day-tripping from the Boston area or elsewhere in the Berkshires, of course it’s still worth visiting Stockbridge! Just prioritize the places you want to visit the most.

And of course, plenty of people make Stockbridge their base for a week or longer — a lovely and relaxing option! As long as you have a car, you won’t get bored here. There is so much to explore within an hour’s drive of Stockbridge.

A big White House with a small sun room off to the side.
Another angle of Chesterwood, one of my favorite things to do in Stockbridge MA.

How to Get to Stockbridge, MA

If you’re flying into the Berkshires, the closest airport is in Albany (one hour’s drive) and the closest major airport is in Boston (2.5 hours). Again, I recommend having a car to explore the area fully as it’s the best way to get around.

Alternatively, you can take a bus from Boston year-round. Amtrak has a stop in Pittsfield, which is a 25-minute drive from Stockbridge. The Berkshire Flyer is an Amtrak train that runs from New York to Pittsfield during the summer months.

You can rent a car in Pittsfield.

A hotel room filled with 18th century furnishings. Blue walls, a pale peach satin rocking chair, and a long bench at the end of the bed.
A room at the Red Lion Inn in Stockbridge MA

Where to Stay in Stockbridge, MA

There are lots of different kinds of places to stay in Stockbridge. Decide whether you would like to be in walking distance from the downtown, and whether you’d like to be in a busy area or somewhere more isolated.

Top Luxury Hotel in Stockbridge: The Inn at Stockbridge

If you want to splurge for somewhere special to hang your hat, this inn has gorgeous, immaculate rooms in a very pretty wooded setting. If you’re looking for a quiet getaway, this is a perfect spot.

Top Mid-Range Hotel in Stockbridge: Red Lion Inn

As mentioned above, this is one of America’s oldest inns. The historic property is a see-and-be-seen spot in Stockbridge. Don’t forget to have that drink in their iconic speakeasy! I stayed overnight here and enjoyed my stay, but just know that old buildings occasionally have quirks that you won’t have at the big chains.

Top Budget Hotel near Stockbridge: Quality Inn

If you’re looking for budget accommodation in the Stockbridge, there isn’t much on offer — so I suggest you head to the town of Lee, a 10-minute drive away. The Quality Inn is a Choice Hotel and features clean, simple rooms. Lee has some nice restaurants, too.

A little red house perched on a green hill.
Norman Rockwell’s home in Stockbridge MA

Best Time to Visit Stockbridge, MA

The Berkshires as a whole is a wonderful year-round destination. I’ve most recently visited during May, which can be a bit hit-or-miss in New England, but I enjoyed pleasant weather and lots of flowers.

The best time of the year is summer, with lots to choose from in the way of festivals, theater, events, and music. Of course, this also happens to be the busiest and most expensive time to visit, so I’d recommend booking early.

If you’re interested in New England fall foliage, this is the place to be in the first half of October, when the leaf colors are at their peak. This is another busy and expensive time of year.

Winter can be a quiet and cozy time to visit, and it will mainly be locals in town. Having said that, many major attractions tend to shut down during the cooler months of November through March, so I’d recommend doing some research to make sure you can do the things you want to do.

A big white home in Stockbridge MA with a covered porch in front.
Another view of the Red Lion Inn, Stockbridge MA.

Is Stockbridge worth it?

Yes, of course Stockbridge is worth it! I really loved my time here. I think it’s one of the best towns in the Berkshires to visit, and if you’ve explored lots of coastal Massachusetts but nowhere in Western Mass yet — it’s about time you visited!

I hope you have a wonderful time in Stockbridge! This is a special place.

More on the Berkshires:

More on Massachusetts: 

Have you been to Stockbridge MA? Any recommendations?

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