20 Best Things to Do in Stockbridge, MA

Stockbridge, MA
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Nestled in the Berkshire Hills is Stockbridge, Massachusetts, a resort community that boasts a quintessential small-town ambiance.

Its charm and allure have made this an irresistible destination for those who are seeking beauty in nature.

In fact, the town has been the subject or was mentioned in several forms of media, be it music, visual art, or literature.

And who can blame these artists?

The rolling terrain, vast wilderness, scenic lakes, and beautiful historical homes make Stockbridge the ideal muse for expressing the sublime.

But you don’t have to be an artist yourself to appreciate all these wonders, so make this a top choice for a vacation.

Here are the 20 best things to do in Stockbridge, MA:

Explore the Terraces of Naumkeag

Front View of Naumkeag
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Stockbridge has no shortage of historic homes turned into attractions, and one of these is the stunning Naumkeag.

Once owned by a prominent and wealthy couple, this 48-acre destination has expansive gardens and a regal home serving as the heart of it all.

But in Stockbridge standards, the Naumkeag is something entirely different.

View of Naumkeag
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This structure is often called an architectural wonder—one of the best examples of the Shingle Style country house.

The estate contains 44-rooms and has a rustic, almost whimsical feel to it that’s perfectly complemented by the gardens surrounding it.

View of Naumkeag
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And what a sight these gardens are: brick walls with gilded decoration, flower beds along paved paths that are just bursting with colors, terraced grounds framed by sculpted trees, and the iconic blue steps that are unlike any other in town.

It’s quite the experience to walk amongst these strikingly beautiful gardens—you’d almost feel like staying.

Field in Naumkeag
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Smell the Fragrant Blooms at Berkshire Botanical Garden

View of Berkshire Botanical Garden
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Berkshire Botanical Garden takes the landscaped exteriors of Stockbridge’s historic homes to another level.

The 24-acre attraction is something that the town’s residents are rightfully proud of, with 25 areas showing off gorgeous greenery.

And having been around since the 1930s, the place is one of the oldest facilities of its kind in the US.

During your tour, you’d see paths lined with colorful blooms, beds of flowers bursting with color, sections of trees standing in majesty, and man-made rock formations that add a whimsical feel.

View of Berkshire Botanical Garden
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The gardens contain more than 3,000 species of plants, most of which are native or endemic to the Berkshire Hills region.

During most of the summer and early fall, all of the exhibits are open for public viewing.

Outside of this period, some areas are closed because of the chilly temperatures this region experiences.

So check out their calendar to see which sections are open during your trip.

Colorful flowers lined up at Berkshire Botanical Garden
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See Colorful Displays at Schantz Galleries Contemporary Glass

Take a step back from historical art and homes and travel to the present by visiting Schantz Galleries Contemporary Glass.

The modern artworks of this facility may stand in sharp contrast to the other sights in Stockbridge, but they’re a welcome addition to the diverse forms of art in town.

As you might have guessed from the name, this gallery showcases intriguing artworks made entirely from glass.

You’d find stunning abstract pieces, intricate sculptures of animals, multicolored shards and plates, masks and human faces, as well as tentacle-like chandeliers hanging from ceilings.

It’s like nothing you’ve ever seen before!

For sure, you’d be mind blown at the sheer beauty of the displays here, so keep your wits about you and try not to break anything.

See the Works of an Artist at Chesterwood

View of Chesterwood
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Daniel Chester French was a prolific artist in the late 1800s, and he sculpted numerous works of art that now grace national and international museums.

His most famous design is, in fact, the Lincoln Memorial Statue in Washington, D.C.

One of the places he produced many of his well-known pieces is at his summer estate in Stockbridge, Chesterwood.

Because of the significant works Chester did in this location, Chesterwood has been designated a National Historic Landmark.

View of Chesterwood
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His estate is typical of what you might find in Stockbridge: extensive grounds verdant with greenery and sculpted bushes, mountain views framed by landscaped trees, and a Georgian Revival home standing solemnly in the midst of it all.

Today, the house serves as a museum, showcasing samples of Daniel’s work like small sculptures and sketches.

Join a tour and check out all the wonders of this beautiful destination!

View of Chesterwood
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Take Stunning Photos at Monument Mountain

Reaching 1,739 feet in height, Monument Mountain is one of the highest points in the Housatonic River Valley.

This scenic attraction has inspired several painters and literary giants, including Herman Melville, the author of the classic Moby Dick.

In fact, the mystical feel of this whole area has been recognized by early native Americans, particularly the Mohicans.

The pile of rocks atop a cliff, from which the destination is named, is the fabled monument of a maiden who jumped to her death.

But legends aside, Monument Mountain is often visited because of the sweeping views of the Housatonic River Valley.

It’s an ideal location for hiking and landscape photography, especially during fall when the whole landscape is tinged with a hue of red and orange.

Feel the Magic at Ice Glen

Scenic View at Ice Glen
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The first natural attraction in this list is Ice Glen, a place that seems to be taken out of a fairytale.

This ravine is a lush, undisturbed, and romantic attraction that spans around 1.4 miles.

And like Stockbridge itself, this particular spot has been mentioned in classic American literature, all thanks to its beauty.

Scenic View at Ice Glen
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While trekking the route, you’d find yourself amidst moss-covered boulders dappled by pale sunlight, stone arcs that seem like gateways to another world, and old-growth forests that may or may not be hiding actual fairies.

One of the more unique (i.e., magical) aspects of this place is the fact that ice often persists even in summer.

This is all thanks to the landscape of the glen, which reduces the amount of light and heat reaching the ravine.

Hiking trail at Ice Glen
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Explore the Halls of Norman Rockwell Museum

Front View of Norman Rockwell Museum
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Many prolific artists have, at some point, made Stockbridge their residence.

One of these is Norman Rockwell, a famous illustrator who focused on creating artworks that depict the optimistic side of American culture.

In the last 25 years of his life, he lived in Stockbridge and continued to create paintings that graced the covers of magazines.

Front View of Norman Rockwell Museum
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To honor his legacy, the Norman Rockwell Museum was established.

It now has the most extensive collection of Norman’s art, amounting to 574 original pieces.

There are also documents, photographs, fan mail, tools and pigments, and other things Norman once owned.

While visiting, you’ll get a sense of his buoyant and cheerful view of life in America through his vibrant works.

Catch a Show at Berkshire Theatre Festival

Exterior of the Berkshire Theatre Festival
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The performance arts is also a celebrated art form in Stockbridge, and none more so than during the Berkshire Theatre Festival.

This event is the oldest of its kind in the Berkshire Hills region, having celebrated its centennial anniversary last 2018.

And during this historic run, more than 550 fully-staged productions have taken place in various facilities around town.

Many award-winning actors and playwrights have joined the festival, which elevated it into a prestigious event.

Some notable personalities who’ve starred in the productions include Al Pacino, Buster Keaton, and Dustin Hoffman.

Check out their website today to see the schedule and venue of their upcoming shows!

Visit the National Shrine of The Divine Mercy

View of National Shrine of The Divine Mercy
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Even if you’re not particularly religious, you’d still be in awe of the majesty of the National Shrine of The Divine Mercy.

The United States Conference of Catholic Bishops gave the “National Shrine” designation to the chaplet in the 1990s, increasing the number of pilgrims visiting the place.

Upon arrival, you’d immediately witness the grand architecture of the structure, which has the same style as most of the historical homes in the area.

Lawn at the Divine Mercy
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Then there are the vast grounds that give way to forests, covering 370 acres.

Inside is a solemn and modern interior that’s ideal for a few minutes of silent prayers and reflections.

You’d also see the image of the “Divine Mercy” at the altar from which the chaplet is named.

So if you’re looking for a spiritual destination during your trip to Stockbridge, then this is the place to be.

Cruise the Gentle Currents of Housatonic River

Housatonic River is a meandering body of water that traverses the lower half of Stockbridge.

It’s an economically important river that irrigates the surrounding forests and agricultural lands.

And it also serves as a tourist attraction for visitors who want to explore the more secluded areas on this side of town.

You’re welcome to cruise the gentle currents on a kayak, canoe, or boat and discover some scenic bends or hidden beaches.

There are some areas that have turbulent rapids, but with a seasoned guide, these shouldn’t be much of a problem to you.

If you want to try your angling skills, there are pike, car, bass, and other freshwater species swimming in the depths.

Go Swimming at Stockbridge Bowl

View of Stockbridge Bowl
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As the biggest body of water in the area, Stockbridge Bowl has become the local favorite for those who want to try water-related activities.

It’s also known as Lake Mahkeenac, and it has a total area of 372-acre.

Many people come here to enjoy the gorgeous tree-lined banks, deep blue waters, and views of distant mountains, such as the Yokun Ridge.

View of Stockbridge Bowl
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You can try swimming, fishing, boating, kayaking, and a host of other activities here, except for jet skiing, which is not allowed.

During winter, the whole lake freezes over, making it an ideal destination for ice fishing.

But if you’re not a fan of water, you simply stay in one of the many parks and campsites surrounding the lake.

It’s a great place to spend time with your family!

Visitors swimming at Stockbridge Bowl
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Explore the Interior of the Mission House

The Mission House is a historical home that may be seen in Stockbridge, Massachusetts.

It was constructed between 1739 and 1742 by a Christian missionary to the native Mahicans.

Facade of Mission House
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It is a National Historic Landmark established in 1968 in recognition of its rarity as a surviving historical mission building.

Before being relocated to its present location for preservation, the house stood guard over Stockbridge for over 200 years.

The home features a typical Georgian center-hall arrangement,  a parlor on the left, and a kitchen on the right, both of which have fireplaces.

The central hall also includes stairs leading to the second level.

Beautiful fenced garden at Mission House
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A superbly maintained example of a front door from the Connecticut River valley covers the front entrance.

There is a second entry on the right side of the house, and a short corridor leads from that entrance to the office, which differs from the conventional Georgian design.

Discover the Wonders of a Play by Berkshire Theatre Group

Attending a play by the Berkshire Theatre Group is among the greatest summer activities in Stockbridge.

The Berkshire Theatre Festival launched in 1928 in Stockbridge, and The Colonial Theatre, established in Pittsfield in 1903, were combined in 2010 to become the Berkshire Theatre Group, one of the county's oldest cultural institutions.

The Berkshire Theatre Group, one of the region's biggest and most interesting arts groups, is in charge of the creation, production, and performance of theater, music, and other performing arts.

The renowned four stages of Berkshire Theatre Group are a precious cultural asset for the community and showcase the evolution of American theater.

A summer getaway with the Berkshire Theatre Group is the best way to see anything from plays to concerts to movie premieres!

Explore the Streets of Stockbridge Town Center

Stockbridge, a gorgeous community that still resembles how it did before artist Norman Rockwell began operating in his studio above Main Street, is lined with boutiques, galleries, and delightful stores.

The lovely town center is where so many of Stockbridge's greatest activities begin!

It is bustling with activity and has several wonderful cafés and neighborhood eateries.

This region appeals to antique enthusiasts, souvenir seekers, art collectors, art pieces, high-end apparel, antique jewelry, creative gifts, specialty cuisine & wine, and home furnishings.

It's always a fantastic time to be in Stockbridge, whether the wildflowers are in bloom in the springtime, the trees are turning color in the fall, or you happen to catch a snowy evening.

Shop at Williams & Sons Country Store

In a traditional country shop, they provide all things Berkshire County, including jellies, syrup, honey, candy, candles, cards, bath products, locally manufactured goods, cider, books, puzzles, and more.

Since the 1790s, Williams & Sons Country has had a store in their shop.

They have been highly recognized for the arts for more than a century.

They are pleased to promote their work by selling various books and artwork created by regional artists.

Additionally, they include unique items to preserve the beauty and distinctiveness of their little portion of the world.

Spend the Night at Red Lion Inn

Red Lion Inn decorated for christmas
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The Red Lion Inn, situated in Stockbridge, Massachusetts, is one of the most iconic Berkshire hotels in the region.

The Red Lion Inn is a well-known institution whose warmth and charm represent ageless history while bringing luxury hotels to Berkshires.

Signage of Red Lion Inn
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It is the location of Maple Glen, a 17-room inn with an unconventional take on modern country.

On the site, there are many adorable village cottages and numerous interesting places to stay, including their Firehouse from the turn of the century.

Interior view of Red Lion Inn
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Additionally, they provide four eating options, ranging from their renowned Main Dining Room to their outside Courtyard available in the summer.

The cuisine in the dining room combines traditional favorites with modern takes on classic New England dishes.

Other Things to Do Nearby

After your tour of Stockbridge, why not visit these other attractions in the surrounding areas?

Join an Event at The Mount

View of The Mount
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Edith Wharton is a celebrated American author who wrote classics like The Age of Innocence and the House of Mirth.

The Mount is the estate where she did most of her work, treating it as the place she can truly call “home.”

And it’s no wonder she wanted to stay here, as the property is almost of palatial standards, with vast sprawling grounds and a home styled after British country houses.

View of The Mount
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More than 50,000 people visit the location every year to marvel at the sights or attend some of the events held within the expansive house.

These include dramatic readings, workshops, lectures, and small film showings.

Marvel at the Views of Olivia’s Overlook

View from Olivia’s Overlook on a winter day
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At the center of the Yokun Ridge is Olivia’s Overlook, a panoramic clearing that offers uninterrupted views of the surrounding hills and plains, including the aforementioned Stockbridge Bowl.

This hidden gem is well worth the trip, as the scenery here is something straight out of a painting, whatever the season is.

Even the trails are attractions by themselves.

The first is the Charcoal Trail, located south of the ridge and nearest to Olivia’s Overlook.

It’s a strenuous hike that brings you to the deeper parts of the ridge before ascending steeply into the destination.

On the other hand, Burbank Trail loops around the ridge and brings you to some other locations like Jackson Pond.

It’s much longer, but you won’t need to exert as much effort climbing the gentle route.

Make a Stopover at the Ventfort Hall Mansion and Gilded Age Museum

View of Ventfort Hall Mansion and Gilded Age Museum
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Lenox is a neighboring town north of Stockbridge that offers similar attractions.

So if you can’t get enough of the beautiful colonial homes, then be sure to visit this community, as it is only a few minutes away.

One of the more well-known of Lenox’s attractions is Ventfort Hall Mansion and Gilded Age Museum.

This stately property is built after the Jacobean style, with imposing architecture and facade composed mainly of brownstone.

Sculpture at the garden in Ventfort Hall Mansion and Gilded Age Museum
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Because of its beauty, it has been used as a setting for many movies and TV series, most notable of which is the Academy Award-winning film The Cider House Rules.

The home itself has been turned into a museum in order to preserve the artifacts and furnishing used by long-gone residents.

Join a tour and see the grand staircase, antique furniture, and other items that show glimpses of the Gilded Age.

Examine Abstract Art in Frelinghuysen Morris House & Studio

George L.K. Morris and Suzy Frelinghuysen were two prolific abstract artists nationally recognized for their intriguing works and lives.

They owned a home in Lenox, which is now listed under the National Register of Historic Places.

Built with influences from the Bauhaus movement, the immaculate-white structure is a work of art in itself.

Inside, you’ll see an interior with decor and furnishing left there by the artists.

During your tour, you will also find some of their work, such as cubist frescoes, paintings, sketches, and photographs.

Final Thoughts

Human talent and creativity are put in the spotlight here in Stockbridge, with its many galleries, architectural marvels, and performance venues.

The muse of these artists is often the beautiful natural features of the town, which has inspired many works of art, literature, and music.

To experience all these wonders for yourself, make this place your top option for a weekend getaway.