The Berkshires at a Glance

How do you begin to encapsulate a jumble of charming towns, one city and a host of iconic sites located within one large geographic area? Let’s try. First of all, know that The Berkshires refers to the part of western Massachusetts situated at the tail end of Vermont’s Green Mountains. So The Berkshires refers to both a region and the mountains. (They’re actually more like rolling blue-green hills with Mount Greylock, the highest point in Massachusetts at just under four thousand feet, as its pinnacle.)

It’s a verdant region (except beneath the snows of winter or the golden glow of autumn) oozing with New England charm and character. The hills remain dotted with cows and orchards and the streets are peppered with historic homes and quaint businesses. Less than a three-hour’s drive from New York City and Boston, it’s no wonder this bucolic play land has been a favorite place for big city people to escape to for centuries.

Let’s start with Stockbridge in the heart of The Berkshires, one of the most picture-perfect small towns in America. The great American painter, Norman Rockwell, captured views of Stockbridge and its inhabitants in many of his works, endearing scenes that appear much the same in today’s real life tableaus. With its splendid historic homes and wide, tree-lined Main Street, Stockbridge resembles a movie set for hometown, USA. And best of all, it’s as authentic as can be. Be sure to stop into The Red Lion Inn, a landmark hotel and restaurant, established in 1773.

The richly forested area of nearby Lenox lends itself well to Tanglewood, the summer home of the Boston Symphony Orchestra. It’s also the ideal setting for a yoga retreat and you can experience one of the best in the country at Kripalu, a center for health and well-being perched upon the undulations of The Berkshires.

All of these Berkshire towns boast a host of good restaurants and shops, largely within interesting locales such as historic buildings or renovated industrial spaces. You’ll find one of the biggest, best and most hipster selections in Great Barrington.This progressive town, along with Lenox, are often ranked among the best small towns in America

Named after Samuel Adams, a leader of the American Revolution and signer of the Declaration of Independence, the old mill town of Adams, Massachusetts is also the birthplace of Susan B. Anthony, another sort of revolutionary that played a pivotal role in the women’s suffrage movement. You can visit the Susan B. Anthony Birthplace Museum, housed in a nineteenth–century homestead, on the outskirts of Adams.

North Adams, a town that was booming with small-scale industry for centuries, more recently became a big center for the arts. (Way to repurpose those old warehouses!) More on that in The Berkshires Arts Scene.

How is it that some of the most picturesque destinations also happen to be college towns? As is the case with Williamstown, home to Williams College, a revered center for higher learning founded in 1793, it’s all about the history. Our founding fathers, and those carrying out their principles, knew the importance of a good education, so this college was established with the funds from the estate of one of America’s original colonists, Ephraim Williams. And as they say, the rest is history. Ain’t that the truth because within this little town and on the Williams College campus you’ll feel like you just stepped into colonial America replete with a village green and other divine grassy spaces.

Pittsfield, the largest city in The Berkshires, and one that has experienced a renaissance of sorts in recent years, is also steeped in Old World grandeur. Many of its buildings are listed on the National Register of Historic Places and bear testimony to the fact that Pittsfield–much like other parts of The Berkshires–once thrived on industrialism, partly due to its location along the Housatonic River. Thankfully, yesterday’s industry has given way to today’s tourism throughout much of the region, which means you will find beauty in The Berkshires in both urban and rural settings.