TBT: Pittsfield, Massachusetts


In honor of Labor Day weekend, I want to revisit this very weekend last year.

First off, I want to make clear that I have nothing against Pittsfield–or the Berkshires in general–as a place. But I have something against it as a road-trip destination for a couple in their late 20s.

Last Labor Day, I gave Jake a chance to pick our road-trip destinations, for once, and he planned a baseball-themed jaunt through Baltimore, Cooperstown, Pittsfield and Connecticut. Only, as it turned out, the Pittsfield part wasn’t baseball themed.

When we arrived, I asked Jake what it was he’d wanted to do there, and he honestly couldn’t remember. To this day we’re not sure how it became part of the plan. But let me tell you–it didn’t last long.

I maybe should have been tipped off by the fact that there were no reasonably priced places to stay in the area–B&Bs looked ornate and were priced like fancy hotel rooms. Many of them also had two-night minimums, and we only wanted one.

There were also no decent-looking restaurants on Yelp or TripAdvisor. Again, warning sign.

But it just didn’t occur to me that the entire area–and one I’ve heard good things about, too–could be completely geared toward retirees. Oh, how it was, though.

We first pulled into Pittsfield to find…not much, save a British and Irish food specialty store that, no joke, was called Brits R U.S. In a town with not much else visibly going on, this shop delighted me in the sheer absurdity of its location.

After about half an hour of walking around, though, we knew we had to find something else to do. We’d heard great things about Tanglewood in Lenox, but the only show playing during our trip was about to end, so we raced over to catch the final bit of it. It was a Tony Bennett performance. He looked and sounded about 100. We were the youngest people there by a good 40 years.

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The Tanglewood area itself was beautiful–great mountain views, nice grounds to walk around. It got rainy though, and with no other ideas for what to do, we basically hung out in the B&B the rest of the day.



We did try going out for dinner, but when we got to Stockbridge–which featured the only place within a few towns that was open on a Sunday night (sigh)–it was stuffed to the gills with old people watching another old person play acoustic guitar. And it smelled like mothballs. We turned right around and went back home.

I will say that we managed to redeem the Massachusetts portion of the trip the next day, when we took a drive through Beartown State Forest on our way to Connecticut. But that’ll be the last time I visit the Berkshires for urban exploration.

Beartown State Forest
Beartown State Forest


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