“What state are we in now?” I ask my cousin, Joe, more than once as he navigates the backroads in the corner where New York, Massachusetts and Connecticut come together.
I can be forgiven for not knowing where we are for several reasons.
The roads here continually crisscross the three borders, and cell phone coverage is spotty to non-existent, so there’s no checking Google Maps.
Before our four-day road trip finishes, we will have explored or traveled through the picture-postcard towns and villages of Stockbridge, Mass.; Sharon, Conn.; Millerton, N.Y.; Great Barrington, Mass.; Lakeville, Conn.; Copake, N.Y.; Lenox, Mass.; Salisbury, Conn.; and Pittsfield, Mass.
It’s a strange sensation for us Westerners who can drive for hours without crossing state borders.
And the most confusing thing of all?
The elusive designation known as “the Berkshires.”
During our five-day trip, we are in and out of “the Berkshires,” a phrase that generally refers to the highly visited north-south strip of land on Massachusetts’ western border that also touches Vermont, New York and Connecticut. It’s a place where you start out hiking in New York and 10 minutes later you are in Massachusetts.
But here’s where it gets even trickier.
The Berkshires or the Berkshire Mountains are only known by that name in western Massachusetts. In Connecticut, they become, among other names, Litchfield Hills — perhaps a more accurate description because these so-called (very old) mountains are more akin to (very big) rolling hills. The Berkshires does have a highest peak — more of a summit, I would say. At 3,492 feet, Mount Greylock does afford quite a spectacular view of up to 80 miles of countryside that encompasses Massachusetts, New York and Vermont.
Another thing: When Massachusetts locals refer to “the Berkshires,” they mean Berkshire County in the western part of the state that was founded in 1761, but (get this) its governing body was abolished in 2000. So today, Berkshire County exists as only a geographical entity, but a much beloved one.
Lastly, don’t confuse the phrase “the Berkshires” with Berkshire, Conn., an unincorporated community in Fairfield County; or Berkshire, N.Y.; or Berkshire, Ohio; or Berkshire, Vt.
Confusing for sure, but the bottom line is that this is a beautiful piece of America, especially in the fall. It gives us bucolic farms, quaint towns, Christmas-card churches, verdant parks, waterfalls, scenic trails bordered by golden oaks and scarlet maples, and a ton of history.
It is the visual definition of the Norman Rockwell America many of us remember from the covers of the Saturday Evening Post because, well, this is where the artist/illustrator lived and worked. A collection of his sketches, paintings and photographs, as well as his studio, can be seen at the Norman Rockwell Museum in Stockbridge, Mass., which is where we serendipitously came across my brother, Charles, and his wife, Margaret, from St. Louis. (What are the odds?) They had come to celebrate a milestone birthday with a bucket-list New-England-in-the autumn road trip.
We toured the studio together, sampled the apples hanging heavy on the trees dotting the museum grounds, hugged mightily and went our respective ways.
E’Louise Ondash is a freelance writer living in North County. Tell her about your travels at firstname.lastname@example.org