James Taylor was right. Despite having hailed from Chapel Hill, North Carolina, he really nailed Massachusetts. And while I was visiting the Berkshires in Western Mass for the first time in my life, the lines from his song “Sweet Baby James” kept going through my mind: 

Now the first of December was covered with snow

So was the turnpike from Stockbridge to Boston

The Berkshires seemed dream-like on account of that frosting

With ten miles behind me and ten thousand more to go

I grew up in Acton, MA, in the eastern part of the state, not too far from Boston. For me, anything west of Route 495 was “Western Mass.” I did make some forays west of Acton during my childhood, including several long cycling trips out as far as Northfield, but I do not recall ever visiting the Berkshires. 

While growing up in Acton, I did plenty of traveling with my parents. Mostly we traveled vertically, from Mass down to New York City to visit my uncle and aunt, or to Delaware to visit my mother’s parents. We also did a lot of traveling northward, to Maine and New Hampshire mostly. We spent plenty of holidays vacationing in Maine, and lots of time in New Hampshire. When we wanted to go skiing, we went to Maine or Vermont. When we wanted to climb mountains, we went to the White Mountains of New Hampshire. The idea of traveling westward in our home state to do any of these things just wasn’t on our radar screen, or so it seems.

Perhaps for this very reason, the Berkshires always did seem mysterious and dream-like to me. I do recall having dreams about traveling to western Mass. and climbing mountains there. And since this meant traveling westward, that vector opened up the dreamy vista of traveling across America, something that I’ve never done (at least, not by car).

So, this summer, while still sheltering with my parents in my hometown, I decided to indulge my curiosity and travel out to the western edge of our state. I wanted to take my daughters on a road trip. Given the conditions of the current time of COVID, we didn’t intend to travel far. The Berkshires seemed like an ideal place to go. We hadn’t been there before, and there would be plenty of places to hike and to experience scenic vistas. 

We left Acton on the morning of July 6 and took Route 2 all the way out to western Mass. An hour later, we reached the French King Bridge, where we stopped and walked on the bridge to take in the stunning view of the Connecticut River. After that, the hills got steeper and the vistas began to open up, with rolling green hills, farmland, and fields stretching into the distance. The girls remarked that it seemed more like New Hampshire than Massachusetts.

We arrived in Lenox that afternoon and settled into the Cornell Inn, a quaint hostelry located on the hilly road leading into the main town. The proprietor recommended that we take a walk in the nearby Kennedy Park, and so we did. We barely scratched the surface of the park, which has forest trails running through hundreds of acres of land. And relating to my previous posts, I’m pretty sure I saw the wings of a Barred Owl during our hike.

The next morning, we drove for about an hour down to the southwest corner of the state to visit Bash Bish Falls, the largest waterfall in Massachusetts. We passed through part of New York State to get there, and then took a ¾ mile hike up to the Falls. They were glorious. Most hikers wore masks, which is always a good sign that here in Mass. we are taking the pandemic seriously.

After stopping at a roadside diner for lunch (the line was spaced out and everyone wore masks) and eating in our car, we took a 2-mile hike around Benedict Pond, and then returned to Lenox for dinner at a local restaurant. The food was pricey, but worth it. We ate outside at tables, while the restaurant took all the necessary precautions.

The next morning, we stumbled upon another fine 2-mile hike, known as Tyringham Cobble. The hike starts in a meadow and climbs a few hundred feet to the peak of a local mountain for a nice view of the valley below. The hike features some striking rock formations, including “Rabbit Rock.”

It also coincides with the Appalachian Trail. While hiking along the AT, we ran into a couple of through hikers with big packs and walking sticks. One of them told us he was on his way to Katahdin in Maine, and I felt a twinge of envy. The girls really enjoyed this hike and later they told me it was the best one we did.

That afternoon it was threatening to rain, so we explored some nearby towns by car. But first, we checked out a chocolate shop in Lenox that was reputed to have some of the finest chocolate in the country. Pretty soon, the girls were high on chocolate drinks, and were giggling and bouncing in the car as they played their favorite pop tunes, which Dad had to endure for most of our trip.

We headed over to Pittsfield. We were surprised to discover that it seemed like a small city by comparison, with tall stately buildings lining its main street. It also had more of a working-class vibe than Lenox, which smells of “daddy’s money” according to my precocious daughter.

For dinner, we found a tiny Greek-Italian restaurant run by a real mom-and-pop couple and had pizza, lasagna, and salad. The girls said it was the best meal of the trip. This was the only time we ate inside the restaurant, which had only a few other customers in carefully spaced seating arrangements. While we were eating dinner, the rain came down, and then it quickly dispersed. Following our meal, we took a leisurely drive back to Lenox, again passing through New York State, and saw a rainbow over the hills. By that time, the sun came out and the view overlooking the lake below was magnificent.

On our final day, we checked out of the hotel and drove all the way to the top of Mt. Greylock, the tallest mountain in Mass. We spent some time taking in the phenomenal view from the mountain top, where we could see all the way to our own eastern part of the state. Then we drove down the mountain, along with a bug that hitched a ride on the windshield, and had a quick lunch in North Adams—unfortunately, most of the interesting things in the town were closed. Then we headed back to Acton via the scenic byway known as the Mohawk Trail, where we were treated to more gorgeous mountain views as we followed a river down the mountains and headed back eastward.

All in all, it was just like James Taylor sang it. Now we have a much deeper appreciation of the true beauty of our home state of Massachusetts. I hope to go back to revisit Western Mass. in different seasons and in better times.