The Berkshires Gilded Age Re-Visited
A Tribute Parade

The vintage carriages were polished like mirrors, the brass buckles and harnesses gleamed, and the prancing horses were glistening against the fall foliage on a perfect day in the Berkshires.

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Ladies and gents gather for the bi-annual coach parade.  Photo courtesy of Andrea MacCallum.

The carriages gathered in the front of the 1870 Southmayd Farm in Stockbridge MA. The gents in top hats and the ladies (including Martha Stewart) in 20th-century finery departed the coach for a luncheon near the maze, gathering above the oxbow of the Housatonic River on land once owned by Henry Wadsworth Longfellow. It could be 1900, but it’s actually Columbus Day 2016 and it’s the bi-annual coach parade organized by Harvey Waller of Orleton Farm. A tribute to the Gilded Age.

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The Housatonic River runs through Southmayd Farm

The Berkshires (pronounced “Berk-shers”) first became popular for second or third homes during the post-Civil war era called the “Gilded Age”.  Society people, largely from NY, and literary and artistic luminaries were drawn to the clear mountain air, pristine hills, valleys, and lakes – a true refuge. The Astors, Westinghouses, Vanderbilts and their peers spared no expense in building mansions that they dubbed “cottages” in deference to their less formal settings than Newport.

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Southmayd Farm is a 33+ acre estate with additional land available for purchase.

According to Cindy Welch, Berkshire Project Manager for LandVest, “Privately held extant Berkshire cottages, such as Southmayd, are a rarity.  Most have either become museums or been developed as resorts.”

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The Bellefontaine Mansion is now part of Canyon Ranch in Lenox, MA.  Photo courtesy of Canyon Ranch.

One such cottage is Shadowbrook, which was built by Mr. Anson Phelps Stokes. At 410’ long in 1894, it was the biggest house in America. In 1956 the house burned to the ground.  It is now the site of world famous Kripalu.  Bellefontaine is now Canyon Ranch. Colbrook is now Cranwell Resort. Blantyre and Wheatleigh are now resorts. Naumkeag is owned by the Trustees of Reservations. The Mount, once owned by Edith Wharton, is a popular public visitors’ site.

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Visitor’s stroll through Wharton’s restored gardens at The Mount. Photo courtesy of The Mount’s Facebook page.

Welch has sold two Gilded Age properties in Lenox, MA. One with ten bedrooms was sold to a Brooklyn, NY couple who plan to use it as second home for their large extended family. The other property was sold to a Boston couple who will also use it as a second home.


Currently, Cindy has 3 “Cottages” listed with LandVest, the grandest of which is Southmayd Farm on 33 acres in Stockbridge.

Southmayd Farm | Stockbridge, MA | $7,900,000

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The house, studio, pool, barns and greenhouse, set on 33+ acres, have been authentically restored to the finest detail. It is museum quality for comfortable country living.

Clipston Grange | Lenox, MA | $1,995,000

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Clipston Grange is in a walk-to Lenox town location and is in move-in condition, ideal for entertaining.

Morewood | Pittsfield, MA | $3,800,000

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The Morewood is adjacent to the Pittsfield Country Club’s golf course and has, like Southmayd, been lovingly restored to magnificence.

Despite the passing of a century, New Yorkers still comprise the largest single segment of second home owners in the Berkshires.

To find out more about these listings or other Berkshires Luxury Real Estate listings, contact broker Cindy Welch at