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The Berkshires: Hills Of Heaven

June 2024
6min read

The mountain ranges that hikers and campers speak of with familiarity and affection—the Adirondacks, Smokies, Catskills, Rockies, Berkshires—are all but unknown to me. When I was old enough to plan my own vacations, air fares to Europe were so cheap and my hold on high school French so uncertain that it seemed prudent to nail it down every few years with a trip abroad. If I chose to stay on American shores, I was drawn irresistibly to the ocean. So when I set off for the Berkshires last fall, it was unfamiliar territory. It soon became clear why the area inspires such loyalty.

The Berkshires are really hills more than mountains, it turns out, none rising higher than thirty-five hundred feet. The Mahican Indians, who lived and hunted there in the seventeenth century, were largely driven out by Dutch and English settlers in the eighteenth, people who proved their mettle during the Revolution. In the summer of 1774 Berkshire residents seized the Great Barrington Courthouse to prevent the royal judges from meeting, and fifty-seven of the Green Mountain Boys who helped Ethan Alien seize Fort Ticonderoga in 1775 were from the Berkshires.

Not long after the Revolution, the artists and writers who are so helpful in turning rural areas into popular resorts began to arrive: the poet William Cullen Bryant; the novelists Catharine Sedgwick, Herman Melville, Nathaniel Hawthorne, Edith Wharton; the sculptor Daniel Chester French. On their heels came the lawyers and businessmen and their thirty- and fifty-room cottages. They built so many of them that the region became known as the inland Newport. A number of residents apparently pondered the absence of waterfront and decided that it hardly mattered: French called the sight of Monument Mountain from his front door the “best dry view” he had ever seen, and the landscape gave Melville a “sea feeling....I look out of my window in the morning when I rise as I would out of a porthole of a ship in the Atlantic.”


Route 7 runs north and south through the Berkshires, beginning at the southern Massachusetts border with the village of Ashley Falls, site of the oldest house (1735) in Berkshire County. Here Col. John Ashley and his neighbors drafted the Sheffield Declaration in 1773, resolving that men were equal and should have the right to enjoy their property without a lot of interference from Great Britain. Then comes the town of Sheffield proper with its cluster of antique stores and the oldest covered bridge in Massachusetts, followed by Great Barrington, where, in 1886, William Stanley lit up Main Street with the world’s first alternating-current electric power system.

But the heart of the Berkshires is probably the stretch between Stockbridge and Pittsfield. Stockbridge’s most famous resident was Norman Rockwell, who moved there in 1953 and used the town as the setting for a number of his paintings. The Corner House is a museum devoted to exhibiting his works. On Prospect Hill above Stockbridge is Naumkeag, the twenty-six-room house Stanford White designed in 1885 for Joseph Choate, the New York lawyer who became ambassador to the Court of St. James’s. The name is an Indian word meaning “place of rest,” and the seven acres of formal gardens are still a good place to spend an afternoon. And no traveler should bypass Mission House, built in 1739 for the Reverend John Sergeant. Sergeant was the first missionary to the Mahican (later the Stockbridge) Indians and was prepared to live humbly among them, but he married a woman with grander plans. The house was constructed with a conspicuously elaborate Connecticut doorway, and the chimneys were placed off the center line of the house to make the front rooms larger than usual. (The Indians called on Sergeant in the more cramped quarters at the back.) In 1928 Joseph Choate’s daughter Mabel bought the house, moved it to its present site on Main Street, restored it, and filled it with colonial antiques, a handful of which actually belonged to Sergeant. A tour takes less than an hour and is time well spent.

Just west of Stockbridge is Chesterwood, the summer home and studio of Daniel Chester French, creator of, among other works, the statue of Lincoln for the memorial in Washington, D.C. Of all art forms, I’m least drawn to sculpture, especially the idealized figures of “Truth” and “The Western Hemisphere” so beloved in French’s era. But I’d hardly stepped through the door before a guide grabbed my interest, pointing out a birdwatching notebook French had kept as a boy and a wedding dress French’s bride never wore because, when the great day came, it was so hot in Washington she decided to get married in something else. The guide then went on to make French’s sculptures come alive for me. She even had an explanation for pointing tools, used in that process I’ve never understood whereby a small figure sculpted in clay by French becomes an enormous statue carved in marble by six Italian brothers in the Bronx. There was also an oddly affecting home movie of French and his friends dancing and carrying on at Chesterwood in August 1925—the movie turned up in a neighbor’s attic, and the staff dated it based on the sculpture he was working on and the English flower border in bloom in the background. After touring the house, you can visit French’s studio and see more accouterments of the sculptor’s trade, including the ingenious railway French had built so he could roll his works outdoors and the sweet-faced, life-size “lay figure” he propped into position when his real model was taking a break.

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....”

The heart of the Berkshires is the stretch between Stockbridge and Pittsfield.

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


The best months to visit the Berkshires are May to October. Music and theater fans will want to aim for July and August to take advantage of the various summer festivals. Leaf watchers should plan tours through the countryside in late September or early October. For visitors who prefer to avoid the tourist season, I would especially recommend May or June and the week or two after Labor Day.

Start by calling the Berkshire Visitors Bureau (1-800-BERKSHR) for a copy of their summer guide. Published every year about April 1, it contains theater, music, and dance schedules, hotel and restaurant listings, hours for museums and houses, et cetera. While waiting for it to arrive, hunt up a copy of The Berkshire Book (1986), by Jonathan Sternfield. It offers a complete guide to history, culture, hotels, and shopping in the area. The restaurant reviews are especially useful—outspoken and on target.

For those who want to cover all of the Berkshires, and there are many places of interest both west and east of those mentioned here, it would be best to travel by car and stay in a different hotel each night, being sure to try at least one of the small inns like the Williamsville Inn or the Hancock Inn (in Williamsville and Hancock, respectively). Travelers who prefer to have a home base from which to make day trips will find the best selection of comfortable and historic hotels in Lenox, including the Birchwood Inn (about 1840), the Village Inn (1771), and the Gateways Inn (1902). Also, a couple of mansions have been converted into luxury accommodations, among them Blantyre, a summer cottage built in 1902, and Wheatleigh, an 1893 copy of a sixteenth-century Italian palazzo.

Recommended reading: Berkshire, The First Three Hundred Years, 1676–1976 , put out by the Eagle Publishing Co.; The Berkshire Cottages: A Vanishing Era, by Carole Owens; and Literary Life in Nineteenth-Century Berkshire County, by Luther Stearns Mansfield, published by the Berkshire County Historical Society.

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