Western Massachusetts’s small towns: The ultimate guide

Part of The Curbed guide to Western Massachusetts

Boston-area residents don’t have to travel all that far beyond the region to encounter some of the nation’s most beautiful and picturesque small towns. Several are in Western Massachusetts, about a two-hour car or train ride westward.

These towns are the places that offer the perfect escapes for those looking to leap beyond the hullabaloo of urban life, if only for a weekend or a few days.

Several white and stone-gray buildings in a pastoral setting. — Clark Art Institute.

A modern art gallery. — The view from the second floor at The Williams College Museum of Art in Williamstown, MA. The Williams College Museum of Art is situated at the Williams College campus close to Massachusetts Museum of Contemporary Art and the Clark Art Institute.

Williamstown

Visit if: You love a good museum and you fondly remember college

First and foremost, the town is home to Williams College, a private liberal arts school with about 2,100 students. Its 450-acre campus has its own offerings, including the Williams College Museum of Art and the Hopkins Observatory.

Or maybe just take in the college town’s drags, including Spring Street, with its eateries and boutiques, and Park Street, with its churches and campus buildings. There is also the expansive Field Park off South Street, near the Clark Institute (more on that later), and the 1753 House—a replica of where early settlers to that section of Western Mass. would have lived.

While the above is all worthy of a visit, the crown jewel of Williamstown is the Clark Institute, one of the most prominent museums in New England, if not the United States. It features European and American paintings, sculptures, prints, drawings, photographs, and decorative arts from the Middle Ages into the 20th century. It’s important that you don’t miss roaming the museum’s grounds—mostly a series of decorative ponds—as well.

Two decorative ponds in front of a forest. — The ponds at the Clark Art Institute.

A building with a bell tower on a college campus. — Professor and student commuting to class on campus at Williams College in Williamstown, MA.

A Gothic church that is gray on a college campus. — The Thompson Memorial Chapel on campus at Williams College in Williamstown, MA.

A young woman with a backpack on a college campus. — Astrid DuBois, a student at Williams College in Williamstown, MA.

A mountain of trees. — Great Barrington, Massachusetts.

Tables and chairs before a stage with an arched ceiling. — Inside of the Guthrie Center, located in an old church.

Great Barrington

Visit if: You’re into folk music or into skiing (or both)

Skiers love Great Barrington because it’s a great jumping-off point for some of the best skiing in Western Massachusetts. Dominating the options is the Ski Butternut resort, which includes 22 runs and two terrain parks, and lots of opportunities for lessons.

If you want to spend even more time outside in or near the town, there is East Mountain State Park and Beartown State Forest. And the Appalachian Trail from Georgia to Maine passes right to the southeast of Great Barrington.

Not into skiing or hiking or hiking to ski? You have a few other options.

Perhaps the most prominent plan B for is the Guthrie Center, an interfaith church that folkie Arlo Guthrie founded to honor his parents Woody Guthrie and Marjorie Mazia-Guthrie. It’s located in an old church where a woman named Alice, whom Arlo knew well, lived with her husband. She became the “Alice” in Arlo’s cult classic “Alice’s Restaurant.” There are regular performances and lectures at the Guthrie Center.

You can also check out the Great Barrington birthplace of sociologist, writer, and civil rights activist W.E.B. Du Bois, who was born in the town in 1868. His birthplace, about two miles from downtown, is a National Historic Site.

Finally, the Mahaiwe Performing Arts Center on Castle Street offers myriad opportunities for outings in Great Barrington, from cinema to opera to dance to theater. And, at the end of the afternoon or evening, picturesque Main Street is right around the corner.

A movie house marquee on a street. — Outside of the Mahaiwe Performing Arts Center.

A couple in their pottery and home goods shop. — Andy Pruhenski and Abby Webster, owners of One Mercantile in Great Barrington, MA. One Mercantile is a home goods store in Great Barrington, MA.

Buildings and a church along a main street. — Main street, Great Barrington.

Roads leading out of town toward mountains. — North Adams, Massachusetts.

The exterior of a contemporary art museum created from a converted industrial site. — Mass MoCA, the Massachusetts Museum of Contemporary Art.

North Adams

Visit: If you adore contemporary art and repurposed buildings

North Adams is home to a world-famous museum and boasts a handful of scenic attractions courtesy of the Hoosic River, which runs through it.

Converted out of a former printing factory complex, the Massachusetts Museum of Contemporary Art is one of the largest hubs of contemporary visual and performing arts in the United States. Its dozens of gallery and performance spaces host music, sculpture, dance, film, painting, photography, and theater year-round.

A short stroll or bike ride south from the museum complex is North Adams’s Main Street, which includes a number of eateries, shops, the North Adams Public Library, and other museums-slash-art spaces, including the North Adams Artists Co-op Gallery, a member-run gallery space; MCLA Gallery 51, a space that the Massachusetts College of Liberal Arts runs for mid-career contemporary artists; and the Berkshire Art Museum, which showcases emerging contemporary art. It, too, was born of a conversion, this time of a Gothic church.

Then, farther up and out along the Hoosic, is the Eclipse Mill Artists Lofts, a community of artists in live-work spaces, that routinely showcases the work of its residents.

An old industrial building that now houses a contemporary art museum. — The rear and inside courtyard area of the Massachusetts Museum of Contemporary Art in North Adams, MA.

Sculpture outside of a museum. — One of the many works on view outside of the Berkshire Art Museum in North Adams, MA.

An old movie theater with a marquee. — The Mohawk Theatre in North Adams, MA was opened in 1938 and closed down in 1991.

An artist among work in a live/work studio. — Mary Lum, an artist and professor at Bennington College in her live/work space in the Eclipse Mill Artist Loft building in North Adams, MA.

An old house on well-landscaped grounds. — Naumkeag House.

Stockbridge

Visit: If you’re still bummed Downton Abbey’s off the air

Some of the last things you’ll see driving I-90 west out of Massachusetts are signs for Stockbridge.

There are several attractions in Stockbridge beyond the charm of its streets and gracious buildings, many of which predate the Civil War.

The biggest Stockbridge attraction is the Norman Rockwell Museum. The artist lived in Stockbridge for the last 25 years of his life, and the Robert A.M. Stern-designed museum on the banks of the Housatonic River contains the largest collection of Rockwell art on earth.

Then there’s the 15-acre Berkshire Botanical Garden, which even in winter hosts events, demonstrations, and workshops. You should also check out the Naumkeag House, the onetime 46-acre Gilded Age estate of a noted New York City lawyer, including its 44-room main house that Stanford White designed in the 1880s.

Finally, just wander, gazing upon the village atmosphere of Stockbridge, its quaint inns, and its shops, such as the Williams & Sons Country Store on Main Street.

A storefront on a quiet main street. — The Williams & Sons Country Store from the street.

A tiny house for kids. — A kids playhouse at the Berkshire Botanical Garden in Stockbridge, MA.

Shelves in a country store with all sorts of goods on them. — Inside of the Williams & Sons Country Store.

Spare brick buildings. — Meetinghouse (left white building), Brick Dwelling Building (center) and the Brick Poultry House (right) where art exhibitions are on view at the Hancock Shaker Village in Pittsfield, MA.

A bearded artisan at his workbench. — Gary Cardot in his workshop at The Funky Phoenix in Pittsfield, MA. The Funky Phoenix specializes in the construction and decorating of functional sculptures specifically produced from up-cycled, reclaimed, or otherwise repurposed, less-desirable items.

Pittsfield

Visit: If you’re looking for a kind of Western Mass. tasting menu

The largest town we recommend—Pittsfield has about 42,000 residents—also has the largest selection of things to do and to see. In general, Pittsfield should be seen as a kind of tasting menu for Western Massachusetts.

There’s plenty to do outdoors, including the 237-acre Springside Park within the city limits and the more than 16,000-acre October Mountain State Forest just southeast of the city. Mount Greylock, the highest natural point in Massachusetts, is just north of the city, too.

Check out North Street, home of vendors such as the Funky Phoenix, which bills itself as “the Berkshires’ leading producer of salvage art and home décor.”

The Berkshire Museum on South Street is a kind of sample menu, blending objects from myriad places and fields—think the Boston Museum of Science meets the Isabella Stewart Gardner.

One of Pittsfield’s most famous residents was the writer Herman Melville, who turned out some of Moby-Dick while living on a farm here that he called Arrowhead. The Berkshire Historical Society now maintains that former farm as a museum to the author.

Finally, there’s the Hancock Shaker Village, a former site for the religious sect, which closed it in 1960. After its closure, locals stepped in to preserve the 750-acre expanse as a kind of living museum. There is a museum on site, farm-to-table dining, hiking trails, the giant Round Stone Barn, and more.