As a life-long resident of the Berkshires, there are certain things I take for granted: leaf peepers come with the vibrant fall colors; winter welcomes the return of skiers; and cultural venues blossom with music, dance and theatrics in the heat of summer.

Our seemingly sleepy way of life, paired with our cultural venues and natural beauty have attracted outsiders to our small northwestern corner of Massachusetts for centuries. Most recently, the rolling hills of the Berkshires have been a getaway for the wealthy and well-to-do of the Bravo television series, "The Real Housewives of New York City," as its cast members seek shelter from the hustle and bustle of Manhattan. It was no different in the late 1800s, when an elite social class moved into the southern Berkshires, building lavish "cottages" on their massive country estates, where they entertained one another for two to three months out of the year.


In Northern Berkshire, where the skyline was once filled with religious spires and billowing smokestacks, the landscape is now dotted with long-dormant factories that once housed industrial giants. It's much different than its southern counterpart, where acres of green pastures and wooded borders surround resorts and hotels.

Having grown up in a part of the county where the majority of the remaining red brick factories live on as repurposed offices, studios and galleries, it seems strange that it only occurred to me within the last 5 to 10 years that these large south county resorts were once home to the "Berkshire Cottagers."


So, who were the Berkshire Cottagers? It's a question I needed answered before I could explore the cottages that remain (and are open to the public). I began my research in the New York Times archives, where society articles heralding the opening of individual cottages, balls and dinners for an elite set of New Yorkers began popping up. Names we now associate with banks, appliances, hotels and major corporations — Morgan, Carnegie, Vanderbilt and Westinghouse — filled the pages of Page Six's predecessors. But being keenly aware that there's a minimum of three sides to every story — his, hers and the truth — I knew the society announcements were just the surface. The real tales of the houses and the men who built them were going to be harder to track down.

Luckily, Carole Owens, the foremost authority on the Berkshire Cottages, was willing to shed some light on just who these well-off individuals were and why they came here, over a cup of fresh pressed espresso and pecan muffins at her Stockbridge, Mass., home.

"In the Gilded Age, they were known as 'The 400.' Following the Revolution, there was Mrs. John Jay's dinner list — a list of the social elite. It had about 169 names on it," she said. "Mrs. Astor's list had 400 names — the number of people who could fit into her ballroom [at her Newport, R.I.] estate. She held the first ball of the social season."

An illustration of the Lenox "Tub Parade," which closed out the season in the Berkshires.
An illustration of the Lenox "Tub Parade," which closed out the season in the Berkshires.

In "The First Four Hundred: Mrs. Astor's New York in the Gilded Age," author Jerry Patterson writes that Mrs. William B. (Caroline "Lina" Webster Schermerhorn) Astor ruled The 400 for the last quarter of the 19th century. To be invited to her ball, was to be part of the elite. Those left off the list were essentially banished.

"The 400 did not go anywhere that didn't have credentials," Owens said. "The Berkshires was already established. It already had the approval of the writers and artists who came here. The Hudson River painters painted the Housatonic River just as frequently as the Hudson River ... It was known as America's Lake District at the time. The members of Mrs. John Jay's dining list had already come through here."

And so, the Berkshires became part of the season.

"They spent the spring in Paris, June and July in Newport, August was spent in Bar Harbor [Maine] and in Saratoga [N.Y.]. September and October were spent in the Berkshires. They typically returned to New York in November," she said.

For some, the Berkshires was an escape that bolstered their health.

"There wasn't any industry in Lenox or Stockbridge. They were concerned with their health and believed the mountain air would was good air," she said. "In Newport, there was the sea air; in the Berkshires there was the mountain air."

But for the nouveau riche, places like the Berkshires afforded them more than an opportunity to improve their health. It also gave them a chance to establish an elite class based on money and politics without having to have "old money" bloodlines. This was attractive to those who were establishing their fortunes after the Civil War.

"Why does someone build a great house like these?" Owens asked shortly after I began my recent visit. "It's the same reason they held balls, built museums and owned Brewster Carriages. They were all symbols of superiority. It tells someone I'm a great man."

Lenox, and later Stockbridge, also allowed the elite to establish large country estates. Shadowbrook, once the home of Andrew Carnegie, had 100 rooms and sat on 900 acres.

At the peak of the Gilded Age in the Berkshires, it was estimated there were 70 to 100 Berkshire Cottages. Then the world changed. World War I arrived. The federal income tax was established. The stock market crashed. Eventually, the homes were sold or abandoned. Places like Shadowbrook saw their land carved up and sold off.

"The estates were subdivided. The land was economically too valuable to tie up," Owens said. "A lot of the cottages were razed for the land. Some are private houses. A lot of them burnt down. They were fire traps and they always seemed to burn in the winter."

In 1956, Shandowbrook, then a Jesuit seminary, burned to the ground. The monks rebuilt and eventually sold the property.

While only a handful of the cottages remain, Owens assured me that high society hasn't abandoned the Berkshires.

"Back then, [The 400] were the first celebrities. Everyone wanted to know what they ate, who they wore and where they went. They were so unlike the rich of today. The rich today are not seen or heard, but they are here," she said.

Terms to Know:

If you're going to have a seat at the table in the former homes of the Berkshire elite, here are some terms you should know for dinner conversation:

Gilded Age: A term coined by Mark Twain to describe the period of prosperity enjoyed by the elite class during the post-Civil War and post-Reconstruction era.

Cottage: A house of more than 20 rooms on more than 30 acres. In the Berkshires, these houses were built between 1880 and 1920.

The 400: Rumored to be the number of individuals Mrs. William B. Astor could fit in her ballroom. Astor, who led the social circle of Manhattan elite, could elevate or banish a member of society by simply adding them or removing them from her list. The list did not always include 400 names. At one point, the list was said to only include 319 individuals.

Jennifer Huberdeau will visit and explore the existing Berkshire Cottages this summer, chronicling her experiences and what readers can expect when they visit these local landmarks, as well. She can be reached by email at