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From Gilded to Grounded: Berkshire Cottages, then & now

The first time you see a Berkshire Cottage you may wonder, “What is that?” Because the “cottage” may now be a luxury hotel, a house museum, or even a restaurant. Or it may still be what long ago it was built to be—a private home.

Editor’s note: The spring-summer issue of our print magazine “Out & About with The Berkshire Edge” is now available for free at 140+ high-traffic locations throughout the Berkshires and beyond.  Our magazine focuses entirely on places to go and things to do in the Berkshires during this three-month period. This article is a feature of that issue. Pick up a copy of the print magazine or read it online.

The Berkshire Cottage was a striking symbol of the Gilded Age, a period in American history spanning from the end of the Civil War (1865) to America’s entrance into World War I (1917)—52 years that changed America from the founders’ dream of an agrarian paradise to the astounding wealth of an industrialized country. How did a Berkshire Cottage become such a symbol?

Just 80 years after we won a revolution, wrote the Constitution, and established a country that ousted the royals, we apparently gave social hierarchy a second look. In that brief half-century, America grew exponentially, boomed extraordinarily, and produced an upper crust intent on flexing its monetary muscle.

In The Theory of the Leisure Class (published in 1899), renowned economist Thorstein Veblen explained, “The basis on which good repute in any highly organized industrial community ultimately rests is pecuniary strength. The means of showing pecuniary strength, and so of gaining or retaining a good name, is conspicuous consumption.”     

What better way to demonstrate your newfound wealth than by spending it conspicuously? And what could be more conspicuous than owning a second home—rarely a primary residence—with no fewer than 20 rooms on no less than 30 acres, requiring a staff of no fewer than eight indoor and 50 outdoor domestic workers? The Cottages here (and in glitzier Newport, Rhode Island) were fashioned after European baronial estates—but in America the barons of banking and emperors of industry liked overspending and understating, hence they called their manses “cottages” (wink-wink) for the same reason they called the Atlantic Ocean “the pond.” Turn-of-the-century titans did, however, enjoy playing the role of landed gentry by christening their country estates with aristocratic names. In a country founded upon equality, the nouveau riche was establishing its superiority for all to see. Ostentation was the order of the day.

Not everyone was impressed. Esteemed writer, editor, and literary critic William Dean Howells (deemed the “Dean of American Letters”) summed it up thusly: “Until very recently we had no such [leisure] class, and we rather longed for it. We thought it would edify us, or, if not that, at least ornament us; but now that we have got it, we can hardly be sure it does either.”

With all due respect to Mr. Howells, it did both, at least for one bright, shining moment in our nascent country’s history. The Berkshires would hardly be the same without such manifest splendor, courtesy of the country’s self-appointed nobility.  


Wyndhurst (then). Courtesy Wyndhurst

Rooted in the Past, Leaning into the Future

Once they started coming to the Berkshires, the super-rich came in droves. The number of Berkshire Cottages has been estimated at an astonishing 93. A few were built in Pittsfield, one or two in Great Barrington, and one in Tyringham, but the bulk of these behemoths were (and remain) in Stockbridge and Lenox. They were over-large and expensive to heat and maintain. Many burned to the ground—too massive for local volunteer fire departments to salvage.

Others exist to this day, thoughtfully preserved and adapted to new uses. These properties are hardly staid relics. Their stewards continue to tell the properties’ stories in ways that resonate with a present-day audience. Imagine: You can stroll the very same grounds, eat in the very same dining rooms, take in the very same views as the Vanderbilts and Astors—all through a modern lens. Start your journey with the following Cottages, which are in one way or another open to the public and offer an excellent representation of yet others that could not be included.

Touring the Berkshire Cottages
First stop: Stockbridge

Highwood and Tanglewood 

Some think the Cottages and their millionaire-builders put the Berkshires on the map, when it was the other way around. The cottagers came because of the artists and writers who had celebrated the Berkshires well before the Civil War—and then channeled that creative spirit onto a much bigger stage. Samuel G. Ward built Highwood in 1847—it sits at the highest point in the woods, commanding a spectacular view of Lake Mahkeenac, Bald Mountain, and the Shadow Brook. Here Ward created the first literary salon in the Berkshires, gathering the New York intelligentsia, Boston Brahmans, and Transcendentalists such as Ralph Waldo Emerson and Henry Wadsworth Longfellow.

In 1849, William Tappan and his wife Caroline Sturgis Tappan bought a small farm next door to Highwood and built their own Cottage, eventually naming it Tanglewood. These illustrious neighbors drew many thinkers of the day to Stockbridge, notably Nathaniel Hawthorne, who penned The Tanglewood Tales during a stay. Today the Cottage sits on the grounds of the Tanglewood Music Festival, made possible when the 210-acre Tappan estate was gifted to Serge Koussevitzky and the Boston Symphony Orchestra in 1936 as a permanent home for their fledgling summer series. On August 5, 1937, the premiere concert drew a then-record crowd to its all-Beethoven performance.

Highwood (now). Photo Kelly Cade

In just four years, the festival was attracting over 100,000 visitors to “The Shed” (built in 1938) and Great Lawn, further establishing the Berkshires as a major cultural destination. When the Highwood estate was added, in 1986, the additional acreage allowed a second venue—Seiji Ozawa Hall—to be constructed. 

You can walk freely on the Tanglewood grounds during daylight hours if there is no performance. The Cottages remain in use: Strolling from the main gate, follow the path to the Visitors’ Center (Tanglewood) on your right. Continue with The Shed on your left—Highwood, home to a restaurant, is straight ahead, through a small copse.


H.H. Cook, American real estate tycoon, was so happy that his daughter had married a Spanish Count (bringing a title to the family) that he hired Frederick Law Olmsted, Robert Swain Peabody, and John Goddard Stearns, in 1893 to create an appropriate residence. Wheatleigh was built as all Cottages were: From the porte cochère, you enter the great hall that opens to the spectacular view. Outside there is a terrace.

Behind the Cottage is a lovely, albeit unusual, tower. Tales of all sorts have clung to it, including being a mausoleum for the Countess’s beloved pets, gaining the structure its name: The Poodle Tower. (More likely it was a water tower, but the myth is more fun to imagine.)

Wheatleigh (then). Courtesy Wheatleigh

Wheatleigh is now a boutique luxury hotel (one of the smallest Leading Hotels of the World) and its 19 rooms come with a steep price tag. However, the public has choices. For a much smaller tab, you can sit on the terrace, order a beverage, and take in the view. Or, you may wish to splurge on a meal at the inn’s French-influenced restaurant, The Portico by Jeffery Thomson (by reservation only).


In 1886, a local newspaper wrote, “Outside was slowly creeping into the village. Summer people were buying places . . . down the street the big family of Joseph H. Choate was going to build on a hill . . .”

Choate was a prominent New York lawyer who represented Alva Smith Vanderbilt and twice argued before the Supreme Court against the constitutionality of income tax. (He won.) He also served as Ambassador to the United Kingdom and his wife Carolyn, an artist and advocate for women’s education, co-founded Barnard College.

To build their house on the hill, Choate hired family friend Charles Folsom McKim of McKim Mead and White; Frederick Law Olmstead designed the original gardens on 48 acres. The resulting 44-room Cottage has unrivaled views of Monument Mountain and a mesmerizing allée of linden trees. 

Naumkeag (now). Photo Gabrielle K. Murphy

Unlike other Gilded Age settlers, the Choates resided at Naumkeag—the Native American name for Choate’s birthplace of Salem, Massachusetts—from April to November. After inheriting the property in 1929, daughter Mabel Choate created the renowned gardens that stand today (working with landscape architect Fletcher Steele) and, in 1959, bequeathed Naumkeag and its furnishings and fine art to The Trustees of Reservations.

This excellent example of a Berkshire Cottage is a house museum—and like other such institutions faces the challenge of honoring its heritage while remaining relevant to the times.

“The mission of The Trustees is to protect and conserve the special places of Massachusetts, for everyone, forever,” says General Manager Brian Cruey, Director for the Southern Berkshires at the Trustees. 

It also means introducing Naumkeag to new audiences across the seasons, from the popular “Daffodil and Tulip Festival” in spring to the “Incredible Pumpkin Show” in October and “Winterlights” during the holidays. Summer brings “Naumkeag at Night, with area musicians performing against the spectacular backdrop; bring a picnic blanket and basket, or purchase light refreshments from the snack shack.


Another historic house museum, Chesterwood is operated by the National Trust. Take the tour, and stroll the wooded ramble laid out so many years ago by Daniel Chester French—the sculptor best known for the iconic seated figure of Abraham Lincoln (1922) in Washington, D.C. and the Minute Man (1874) at the Old North Bridge in Concord, Mass.

“Our mission is to preserve Chesterwood and facilitate its full use as an inspirational and inclusive center for artistic creativity,” explains Executive Director Donna Hassler. To that end, Chesterwood offers artist residencies, classes and workshops, and outdoor programs in the performing and literary arts—including an annual sculpture exhibit along that same path.

Chesterwood (now). Courtesy Chesterwood

The Georgian Revival house, finished in 1901 and sitting on 122 acres, was designed by French himself and illustrious architect Henry Bacon of New York City (the two had collaborated on the Lincoln Memorial). The artist also transformed an apple orchard into a formal garden—start there and follow the hydrangea-lined Straight Path to the Woodland Walk, intended as a “classroom of nature.” For a more vigorous uphill hike culminating in a commanding view, take the Ledges Trail, stopping to rest at the panoramic Overlook. 

French’s Studio, a few peaceful paces from the house, is an engineering marvel. Stand in awe of the railroad tracks and flat-bed car, which allowed French to roll his masterpieces outdoors to gauge how they would look in sunlight. You can view hundreds of models and final works in the Studio, Barn Gallery, and Collections Gallery.



The Mount 

Thanks to its celebrated resident and robust programming, The Mount is, for many visitors, the first Berkshire Cottage they encounter. And aptly so—novelist Edith Wharton meticulously portrayed the age, its people, and social prescription in The House of Mirth (1905) and The Age of Innocence (1920).

The Mount began as a collaboration between Wharton and architect Ogden Codman, co-author of The Decoration of Houses (1897). Soon, however, the two fought, and Francis L.V. Hoppin completed the house in 1902. The exterior is based on a notable 17th century English country house (plus Wharton’s wish for an
Italian-inspired terrace), whereas the interior draws inspiration from classic French and Italian design. The library contains Wharton’s own vast collection of books, many with her own annotations and scribbles.

The Mount (now). Photo Kelly Cade

The historic house museum and cultural center carries on its literary lineage with authors’ series, lectures, dramatic readings, theater, storytelling, and musical performances on the expansive terrace (where you can lunch at the seasonal café) or in the stable.

You can always stroll (for free, from dusk to dawn) through the prized gardens, designed by Wharton in concert with her niece, Beatrix Jones Ferrand, then a rising star in landscape architecture. For Wharton, author of Italian Villas and Their Gardens (1904), the gardens were to be elegant outdoor rooms designed in harmony with the house. The sunken Italianate Garden is a highlight—then follow the Lime Walk to the formal French Flower Garden and take in the brilliant display. Juxtaposed against this backdrop is an annual outdoor installation by SculptureNow, featuring new works by prominent artists.

 Ventfort Hall

In the final decade of the 1890s, Sarah Spencer Morgan (sister of J. Pierpont Morgan) and her husband George Hale Morgan purchased land and retained prominent Boston architects Rotch & Tilden to build Ventfort Hall, a Jacobean Revival estate—complete with 15 bedrooms, 13 bathrooms, 17 fireplaces, a billiard room, and bowling alley. Upon completion, in 1893, it was described as “one of the most beautiful places in Lenox.” 

The Morgans’ estate included 26 acres of landscaped gardens with two gatehouses, a carriage house and stable, and six greenhouses. As was the style, Ventfort Hall bears an impressive porte cochère, a three-story great hall, and an elaborate wood-paneled staircase, but it boasted all the modern amenities of the time, including an elevator and central heating.

Ventfort Hall (now). Courtesy Ventfort Hall

Alas, Sarah lived only three years beyond completion; the property passed to their heirs upon George’s death in 1911. By the mid-1980s, after a series of owners and functions, the property was on the brink of demolition until local preservationists banded together to form the Ventfort Hall Association and, backed by generous donations and financing from the National Trust, became the new owners.

The mission of Ventfort Hall today is to replicate a way of life that visitors can experience through regular tours and special programming, including yoga on the lawn.

Wyndhurst and Coldbrook

The ultra-luxe, 121-room Miraval Berkshires Resort & Spa encompasses two repurposed Berkshire Cottages: Wyndhurst, an imposing mansion perched on the hill, and the smaller Coldbrook (renamed Beecher’s Cottage) next door. These historic structures are joined by three modern “carriage houses” and a sprawling spa. Say (and pay) what you will, Miraval offers a chance to experience a Gilded Age past in a modern, mindful lens.

It all started when John W. Sloane and Adela Berry Sloane purchased the property in 1894, having been introduced to the area by Sloane’s brother William and his wife Emily Vanderbilt (daughter of Cornelius), who built nearby Elm Court, itself a prized summer estate. The Scottish immigrant brothers made their fortune as owners of W.J. Sloane & Co., a home furnishing store in New York City.

The Sloanes razed an existing house, but kept its name, hiring architects Peabody and Stearns to design a brand-new iteration. The 34-room Tudor-style mansion of Perth Amboy brick featured electric lighting, marble floors, and other amenities and stood on 250 acres. The plantings in the gardens reflect the philosophy of their designer, Frederick Law Olmsted: shrubbery was massed, emphasis was placed on trees, and harmony was one with the views. A massive stable comprised 16 boxes; a cow barn produced milk and cream, shipped daily to the family in New York.

Nearby Coldbrook began as a small farmhouse owned by the brother of Harriet Beecher Stow (hence the name change). In 1882, Captain (and railroad magnet) John S. Barnes retained Peabody and Stearns to undertake a years-long process of expanding the structure into a rambling manse. Landscape architect Ernest Bowditch worked on the grounds.

Both properties were sold in 1925 to the developers of the short-lived Berkshire Hunt and Country Club. Subsequently, Edward Cranwell purchased Wyndhurst as a summer home, eventually donating the property to a Jesuit group, which operated it as the Cranwell Preparatory School until its closing in 1975. A decade later, new owners opened The Cranwell Spa and Golf Course, which enjoyed a long, illustrious run until 2017, when Hyatt transformed it into Miraval.

While little other than the original staircase remains inside Beecher’s Cottage, Wyndhurst retains much of its grandeur—and breathtaking panorama, now overlooking 380 leafy acres. None other than President McKinley declared the view from the southern terrace “the most enchanting view I’ve ever had” on a visit in 1897. Story has it that McKinley was equally impressed by a ceiling in the mansion’s formal dining room, replicating it at the White House.

Today you can dine in the retreat’s high-end restaurant, Harvest Moon, or book a day spa package, entitling you to the full gamut of treatments, activities (including an aerial challenge course), The Roost smoothie/snack bar, and outdoor Serenity Lounge Pool. 


This former mansion-turned-luxury hotel has a storied history, and its most recent chapter is currently being written. Notably, Blantyre has changed hands for the third time in as many decades. Its latest owner (as of 2021) is interior designer and hotel empresario Ken Fulk, who is spending a purported $90 million on the hotel’s renovation (the second such extensive overhaul), with plans to reopen in September. Time will tell what the urbane visionary’s interpretation of a rural, centuries-old property will be. One thing’s for certain: Michelin-starred Chef Daniel Boulud will remain in charge of the restaurant operations, offering up his distinctive brand of seasonal, French-inflected cuisine.   

What of Blantyre’s true origins? Industrialist Robert Warden Paterson purchased land and summoned architect Robert W. Robertson of New York City to Lenox. Apparently, Robertson drew a rough sketch on the back of an envelope, and the house was built just as he sketched it. 

Blantyre (then). Courtesy Blantyre

Mr. and Mrs. Paterson unveiled their Cottage at a garden party in September of 1904, receiving guests in the music room and then ushering them through the garden and across the width of the house into the conservatory. A famous orchestra played in the south corner of the terrace. All the ground-floor rooms, including the Paterson art gallery, were opened for inspection. Blantyre was born. 

That Blantryre is still standing today, with its Tudor-styled manor and 180-acre grounds intact, is due to the efforts of Ann Fitzpatrick Brown, who received the abandoned estate as a gift from her parents, Jack and Janet Fitzpatrick. She opened Blantyre in 1981 as a summer country house where guests could experience a bygone era; in 2005, after years spent winterizing the property, Brown was able to keep Blantyre open as a year-round retreat.


The last Cottager on record to depart the Berkshires was shipping magnate Giraud Foster, who lived in his beloved Bellefontaine until his death in 1945, just shy of his 95th birthday. 

The completed house was heralded in the July 3, 1897, issue of American Architects & Building News. Foster must have been pleased—he and wife Jan Van Nest had hired the illustrious architectural firm of Carrere and Hastings, designer of the New York Public Library for the Astor family, to allegedly replicate Marie Antoinette’s Petit Trianon at Versailles. Of particular interest is the use of white marble from the quarries in Lee, four miles away.

Bellefontaine (now). Courtesy Canyon Ranch

Soon after Foster’s death, Bellefontaine was sold to the Society of Fathers from Brooklyn, who used it as a preparatory school. Alas, in 1949, a fire destroyed all but the library (and its 5,000 volumes) and rotunda in the interior. The commanding pale brick exterior survived. After being bought and sold multiple times over subsequent decades, Bellefontaine was purchased by the founders of Canyon Ranch, in Tucson, Arizona, who preserved it when creating the second location of the world-class wellness retreat in Lenox (opened in 1989).

The graceful mansion serves as a focal point of the 122-acre campus—and is home to the Integrative Health Center on the second floor and lounges and restaurants below. 

If the price to stay at the all-inclusive resort is beyond reach, the purchase of a day pass gains you full use of the facilities, including spa treatment, fitness classes, and a gourmet lunch. The Culinary Rebel on the Lawn sits on Bellefontaine’s wraparound terrace (with endless views); inside is the more upscale Canyon Ranch Grill. Based on availability, the spa is even open for walk-in services. 

The Story Continues

The Gilded Age faded. War dampened the exuberance for the display of wealth; the Great Depression and income tax choked off the cash flow. Buildings are the repositories of our memories. We take our loved ones to a structure, point, and say, “that is where I was born . . . went to school . . . met your father.” The story flows from the place.

A study done at UMass Dartmouth found the best-loved towns save their historic buildings and in doing so save their unique history. That describes the history-loving Berkshires. Year after year residents and a million tourists are drawn here to dine, sleep, and revel in our historic buildings—and experience America during the Gilded Age.



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But Not To Produce.

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The Edge Is Free To Read.

But Not To Produce.