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A few miles up the road from Chesterwood is the estate called Tanglewood, one of the Berkshires’ primary attractions since the Boston Symphony Orchestra began performing there in 1937. Nathaniel Hawthorne lived on the grounds in 1850–51 and wrote The House of the Seven Gables and part of The Blithedale Romance here. At concert times huge crowds gather to picnic on the grass and listen to music, so it is worthwhile to return when the lawn is empty and the venerable trees and the somber gray-green Victorian house propel you back into the nineteenth century.

Fifty years after Hawthorne left Lenox, Edith Wharton bought property there and began constructing a home along principles outlined in her book The Decoration of Houses . The Mount, as she called it, is undergoing restoration now, paid for in part by theater performances on the grounds. In the meantime the occasional patches of peeling or rust-stained paint somehow improve the place; faded elegance may be the most appealing kind.

About five miles north of the Mount on Route 7, just before Pittsfield, is the sign for Arrowhead, the small, mustard yellow farmhouse where Herman Melville lived from 1850 to 1863. (He finished Moby Dick there in an upstairs room, a book so badly received his reputation never recovered. When he left the Berkshires, it was to move to New York to look for a job.) Melville and Hawthorne met one day in 1850 while they were climbing Monument Mountain, and each found support in the good opinion of the other. The following summer they traveled together five miles west of Pittsfield to Hancock Shaker Village, a community founded in 1790 and dedicated to pacifism, celibacy, equality between the sexes, and communally owned property. Although the last Shakers left in 1960, the village is still there and now operates as a museum. Tours begin in the Brick Dwelling House, the central living and meeting place, where light streams in through oversized windows and rooms are decorated with the handsome, spare furnishings for which the Shakers are justly celebrated. Clustered nearby are buildings for washing and ironing, cabinetmaking, and printing, and a round stone barn designed so that one farmer could feed and milk a whole herd of cows. The guides here make clear that the Shakers didn’t invent the round barn or much else, but, believing they were building for the millennium, they put everything they had into fine workmanship. Hawthorne, however, found that the “women looked pale, and none of the men had a jolly aspect. They are certainly the most singular and be-devilled set of people that ever existed.…”

North of Pittsfield the historical sites thin out and the landscape takes over. You can climb, by car or on foot, Mount Greylock, Melville’s muse, or continue north on Route 7 as it winds through hills and farmland to Williamstown, the home of Williams College (1793). After Williamstown the Berkshires run into the Green Mountains, and you’re in Vermont. As I drove back, the air was turning cold, the trees were turning red, and I wished I could say what Daniel Chester French had said about Chesterwood: “I live here six months of the year—in Heaven. The other six I live, well—in New York.”

—Jane Colihan TO PLAN A TRIP