Western Massachusetts used to be an area I would speed by on the Mass Pike, on my way between Boston and upstate New York. I thought the Berkshires were just for classical music fans and those rich enough to “summer” at their “cottages” (that were actually more like mansions).
But then, this past November, I landed an assignment that offered a week-long trip to the Berkshires. As soon as I began my research, I realized that I had been missing out all these years. Besides its famous outdoor music venue (Tanglewood) and hot contemporary art museum (MASS MoCA), the region offers so much to do that I am already planning my next visit.
I was easily charmed by the natural wonders, cooperative spirit, impressively fresh food, and creative enclaves I found in the Berkshires. Not only is it a beautiful, pleasant area (which I expected); I was surprised to find that it is also edgy, fun, quirky, and innovative.
From the meals to the shops to the hiking trails, I got the feeling that everything is the way it is for a reason: not for the tourists, not for the sake of business, but because people genuinely love and appreciate their home county.
Here’s a sampling of what to do, see, and eat in order to soak up as much of the Berkshires’ unique flavor as you can.
Follow the Food
For those who appreciate fresh, local food, the Berkshires food scene has enough to keep your taste buds entertained for days on end. In most of the United States, sustainable food is a rare alternative to mainstream food choices; but here in the Berkshires, it seems that the majority of restaurants make an effort to source their ingredients locally and ethically.
Chefs manifest this seasonal, regional commitment in creative ways. In Lenox, Nudel changes its menu daily to ensure the freshest possible ingredients. The unheard-of flavor combinations will make you think you’re in some exotic locale, but you’ll have the satisfaction of knowing that most of the food comes from nearby farms. Crimini mushrooms, Brussels sprouts, polenta and bleu cheese, anyone
A local take on a family pizza place, Baba Louie’s (in Pittsfield and Great Barrington) offers organic — and innovative — crusts and toppings. Here, expanding your definition of great pizza to include sourdough, parsnips, and fennel doesn’t mean you’ll have to pay “gourmet” prices; creative and fresh flavors are standard fare. Even if you order a soda, you’ll get a made-in-Massachusetts, additive-free version.
The “farm to table” dining movement is thriving in the Berkshires, but don’t miss your chance to skip the table and go straight to the farm. Small farms abound, and many of them welcome the public. At Rawson Brook Farm in Monterey, visitors can get to know the goats themselves — and even observe a milking session — before buying a tub of creamy chevre.
This dedication to the local extends to the realm of drinking as well. Oenophiles should stop by Furnace Brook Winery, located at Hilltop Orchards in Richmond, for wine, mead, and hard cider made from area grapes, honey, and apples. Tastings run all day, every day, and the first sample is free. And beer enthusiasts can head to the Barrington Brewery in Great Barrington for beer that is not only made on site, but is created using solar energy.
Learn the Landscape
There are plenty of ways to enjoy the outdoors in the Berkshires: depending on the season, you could be hiking or skiing, gazing at foliage or at wildflowers. A hike is never just a hike, though. Local naturalists have put in the work to make sure you learn all about your surroundings.
At Pleasant Valley Wildlife Sanctuary in Lenox, signs, brochures, and knowledgeable staff point out what you should be looking for. On the easy trails around a series of ponds, you’ll see beaver lodges, beaver dams, and beaver-hewn logs. You’ll come to realize that, without the beavers, the landscape would bear little resemblance to what you are seeing today.
Diane’s Trail, located on the site of Gould Farm in Monterey, offers a self-guided tour through woods and wetlands. A booklet available at the trailhead narrates the walk, making you notice details like the shift in ambiance upon entering the forest from the wetlands, and a now-stagnant offshoot of the river you’ve been crisscrossing.
Another example of the intersection of agriculture and nature, Sheep Hill in Williamstown celebrates the region’s pastoral character. Two paths take you up onto striped hills, giving you striking views of surrounding mountains. The former farm buildings provide information and activities designed to teach you about operating a dairy, as well as identifying the plants and animals that occur naturally there
Indoors, at the Berkshire Museum in Pittsfield, you can get a closer look at the birds and mammals, rocks and minerals you observed in the wild. Cases of real stuffed animals from the region invite you to study the crooked neck of a great blue heron, the exaggerated teeth of a beaver, and the widened eyes of several species of owls.
Support Local Artists
You can access well-known art from all over the globe at the Clark Art Institute, the Williams College Museum of Art, and MASS MoCA; and hear world-famous music at Tanglewood. While these attractions are remarkable, there is, of course, an exciting locally sourced arts scene as well.
Pittsfield, once a depressed post-industrial ghost town, has become home to a new wave of contemporary galleries, performance spaces, and artsy coffee shops. Most notably, Ferrin Gallery (well respected for its ceramics) moved to Pittsfield in 2007, creating a vibrant site for art shows, lectures, and other community events.
In North Adams as well, artists have revitalized empty spaces left by discontinued industrial and economic activity. One former textile mill on the Hoosac River has been transformed into galleries, studios, and residences for local artists. Called Eclipse Mill, it showcases ceramics, paintings, books, and more, and is open to the public on weekends.
Even when you’re not looking for art, you’re bound to find it. On the sidewalks of downtown Great Barrington, the recycling bins deserve attention: fifteen local artists were commissioned by a local environmental organization to design the containers out of recycled materials. The result is a fun gallery of accessible art that highlights the importance of recycling.
I stayed at a classic New England B&B, called Hampton Terrace in Lenox. It was very elegant, in an old house with huge rooms; the innkeeper is very knowledgeable about the area.
Another recommended B&B is the Devonfield in Lee.
To avoid the crowds and hear live music in a truly unique setting, make your way to the DreamAway Lodge, right at the edge of October Mountain State Forest in Becket. There, in a cozy living room-like space, the indie artists play in exchange for dinner, tips, and friendly audience participation.
My evening at the DreamAway Lodge was easily one of my most memorable travel experiences, and summed up the whole Berkshires trip in a way. In a large city, this laid-back, quirky music venue would have already become an over-Tweeted, Groupon-listed destination crowded with fashionable people. But tucked away safely in these wooded hills, buffered by miles and miles of winding roads with frequent deer crossings, it happily does its own thing.
Pleasant Valley Wildlife Sanctuary
472 West Mountain Road, Lenox, MA
100 Gould Road, Monterey, MA
671 Cold Spring Road, Williamstown, MA
39 South Street, Pittsfield, MA
The DreamAway Lodge
1432 County Road, Becket, MA
The Clark Art Institute
225 South Street, Williamstown, MA
Williams College Museum of Art
15 Lawrence Hall Drive, Williamstown, MA
87 Marshall Street, North Adams, MA
297 West Street, Lenox, MA
Joanna Eng is a freelance writer and editor based in New York City who blogs about green, ethical travel at GoLightlyBlog.com.
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