The Berkshires

The Berkshires confused me at first. I came expecting wilderness, the way the name sounds, and instead found a landscape of gentle hills, white clapboard towns, and a density of cultural institutions that does not match the size of the place at all. This corner of western Massachusetts has somehow accumulated a major summer music festival, a half-dozen serious art museums, several important theaters, and the former homes of more or less every American writer you studied in school — and yet you can still drive twenty minutes from any of it and be alone on a wooded ridge.

I think the explanation is money and proximity. Close enough to both New York and Boston that the wealthy of the Gilded Age built their summer estates here, the Berkshires inherited a layer of grand houses and the cultural appetite to go with them, and then in the twentieth century turned much of that infrastructure into something the public can use. The result is a region that feels simultaneously rural and absurdly cultured, like a farm town that happens to have a symphony.

Music in a field

The center of all this, in summer at least, is Tanglewood, the open-air home of the Boston Symphony Orchestra in Lenox. You can buy a seat in the shed, but the thing everyone does, and the thing I did, is buy a cheap lawn ticket, bring a blanket and a bottle of wine, and lie on the grass while the orchestra plays into the dusk. Lia, who claims not to care about classical music, fell asleep during the second movement of something and woke during the finale insisting she had heard all of it. The fireflies came out. It was, by some distance, the best concert experience of my life, and it cost less than a cinema ticket.

Beyond Tanglewood the cultural list is almost comic in its length. There is MASS MoCA, an enormous contemporary art museum in a converted mill complex in North Adams, where you can spend half a day and not see it all. There is the Clark, an art museum sitting improbably on a hilltop with a reflecting pool and a collection of Impressionists that would not embarrass a major city. There are the houses — Edith Wharton’s elegant Mount, Herman Melville’s Arrowhead, where he wrote Moby-Dick while looking at a hill he thought resembled a whale.

The hills themselves

But I would not want to leave the impression that the Berkshires are only museums and lawns. The hills are real, and walkable, and in October they turn the kind of colors that make you understand why people drive for hours to look at trees. We hiked up Monument Mountain near Great Barrington, a modest summit with a quartzite ridge and a long view, where Melville and Hawthorne famously met during a thunderstorm and began a friendship. Standing on the same rocks in much better weather, I could see why they stayed up there talking.

The towns reward slow wandering. Stockbridge looks exactly like the Norman Rockwell paintings it inspired, because Rockwell lived there and painted his neighbors; there is a museum of his work just outside town. Great Barrington has become a genuinely good place to eat, full of farm-to-table restaurants that take the local produce seriously. We ate a long unhurried dinner there and then drove back to our rented room through hills black against a sky full of stars.

When to go

Summer is the cultural high season, anchored by the Tanglewood schedule from late June through August, and it brings both the best programming and the largest crowds and prices. Autumn, roughly late September into mid-October, is spectacular for foliage and quieter than you might expect. Winter brings cross-country skiing and a hushed, shuttered charm, while spring is muddy and underrated. Book accommodation well ahead for any summer weekend, and check the Tanglewood calendar before you fix your dates.