Lenox

We arrived in Lenox on a Friday evening in early autumn, the maples along Main Street just beginning to turn, and checked into a bed-and-breakfast that had, a century earlier, been somebody’s guest cottage. That’s the thing about Lenox: in the late 1800s, wealthy families built vast summer “cottages” throughout these Berkshire hills, and though most have since become inns, schools, or museums, the town still carries the unmistakable air of Gilded Age leisure — manicured lawns, stone walls, and a general sense that everyone here is on vacation from something important.

Tanglewood and an evening on the lawn

The whole reason we’d planned the trip around this particular weekend was Tanglewood, the Boston Symphony Orchestra’s summer home just outside town, where a sweeping lawn slopes down toward an open-sided concert shed. We packed a picnic of local cheese and a bottle of Massachusetts-made wine, spread a blanket among hundreds of others doing exactly the same thing, and listened to a program of Brahms drift out over the grass as the sky went from gold to violet to full dark. Nobody around us seemed to mind the informality — families with children asleep on blankets, couples refilling wine glasses mid-symphony — and I understood then why people return to this hillside summer after summer.

The Mount and Gilded Age mansions

The next morning we toured The Mount, the estate novelist Edith Wharton designed and built herself in 1902, its formal Italianate gardens laid out with the same precision she brought to her novels’ social architecture. Walking her book-lined library, it was easy to picture her writing “The House of Mirth” at the desk by the window, the Berkshire hills rolling away outside exactly as they do today. We spent the afternoon driving the back roads between Lenox and neighboring Stockbridge, stopping at Norman Rockwell’s old studio and pulling over more than once simply to look at maple canopies gone fully crimson against white clapboard farmhouses — New England in October doing what New England in October does best.

Getting There

Lenox sits about three hours west of Boston and roughly two and a half hours north of New York City, making it a popular weekend drive from either city via the Massachusetts Turnpike. The nearest airport with regular service is Albany International, about an hour away, though many visitors simply drive the whole way, since the Berkshires themselves — winding two-lane roads through forest and farmland — are part of the appeal. Once in Lenox, the village center is small enough to explore on foot, though a car is needed to reach Tanglewood and the surrounding estates.