I expected western Massachusetts to be mostly rural and without much history, but the Berkshires have plenty of old towns that have been around for centuries. Great Barrington was one of the places that surprised me. A sign near the town hall claims that local residents publicly opposed British rule here in August 1774, shortly before the American Revolution. Whatever the exact claim to fame, the town has a lot more history than I expected to find this far into western Massachusetts.
Great Barrington also felt surprisingly lively for a relatively small town in the mountains. The center had plenty of people walking around, along with shops, restaurants, and historic buildings. It was a good reminder that the Berkshires aren’t simply wilderness; small New England towns are an important part of the region as well.
Searles Castle
Just outside downtown I came across this enormous castle and tried to get a closer look, but signs made it pretty obvious that I wasn’t supposed to wander onto the property. I later learned that this is Searles Castle, a late 19th-century mansion built in the style of an English country castle. It was one of the more unexpected things I came across while exploring the Berkshires.
The building eventually became part of a private school campus, so unfortunately this wasn’t some forgotten castle in the Massachusetts mountains that I could freely explore.
I also photographed this sign simply because of the wording. I’ve rarely heard an American use the word rubbish, which I associate much more with places like the United Kingdom or Australia. Seeing it on an official-looking sign in New England seemed strangely appropriate given the region’s long historical connection with Britain.
Autumn in the Berkshires
I visited the Berkshires during the fall, which is probably one of the best times of year to see western Massachusetts. Forests cover much of the landscape, and the lakes and small towns scattered between the hills make the changing leaves even more scenic. I took plenty of photos trying to capture the fall colors, although none of them quite captured how the landscape looked in person.
Hiking in the Berkshires
Beyond the towns, the Berkshires are one of the best parts of Massachusetts for hiking and spending time outdoors. I did a short hike through the forest during this visit. I didn’t come across any wildlife, but the wooded hills were a completely different environment from the densely populated eastern part of the state.
The biggest hiking destination in the region is Mount Greylock, the highest point in Massachusetts at 3,491 feet (1,064 meters). I didn’t climb it during this trip, but years later I decided that I wanted to reach the highest point of every state in the continental United States during winter. That gives me a good reason to eventually return to the Berkshires and see Mount Greylock under very different conditions, with its summit covered in snow.
