About Connections: Love it or hate it, history is a map. Those who hate history think it irrelevant; many who love history think it escapism. In truth, history is the clearest road map to how we got here: America in the 21st Century
We were all outlanders once. The original settlers came from outside Berkshire. It is even hypothesized that the Indians were seasonal visitors. Nevertheless, we have a strong sense of us and them.
In 1899, a letter written to the editor of the Pittsfield Evening Eagle expressed the feeling:
“It is a reign of summer people. These patronizing pleasure seekers fence off our mountains and valleys and forbid natives to place a foot on them.”
There is vitriol in that letter. Not just a sense of us and them, but a tone of self righteousness about us.

The feeling that people who come from outside ruin our landscape and our way of life, is not a new feeling. Nor is it completely unjustified.
In 1893, Justice Thomas Post received a letter at his law office in Lenox. The letter included a map of Berkshire County, and on it, Becket, Lenox, and Lee were circled. The text was short and to the point: buy anything available in the circled area.
Post set about the task, but he would not tell anyone who his client was. As the total number of acres purchased grew, so did the public’s curiosity.
By 1896, on behalf of his client, Post had purchased 14,000 acres. To imagine the size of the holding, consider this: the land spread over three towns, Washington, Lenox and Lee. The 14,000-acre land mass included forty-two farms, an entire school district, a saw mill, a brickyard, a tavern, and some forestland. The mystery man was now the largest individual landowner in the state of Massachusetts.
Who was he? He was identified as William C. Whitney. Whitney was born in a small town in Massachusetts on July 15, 1841. His father, James, was a shopkeeper with no money but impeccable lineage. He could trace his roots back to Governor William Bradford of Plymouth Plantation.
Cash-strapped, William Whitney attended Yale where – as luck would have it — his roommate was one of the richest men in the United States, Oliver Hazard Payne.
The son of wealth, Payne increased his fortune exponentially by venturing into iron and oil refining. His oil refinery was the first acquired by Standard Oil. Payne served as treasurer of Standard Oil and also had interests in U.S. Steel and the American Tobacco Trust.
Whitney married Payne’s sister, Flora, and received as a wedding present from his brother-in-law, an $800,000 home on 5th Avenue and 57th Street, New York City. Not content to live on his wife’s money, Whitney set out to establish himself in business, politics, and society. He was adept at attracting the richest men of the Gilded Age as business partners. He established a system of electric trolley cars in New York and Pittsfield. He served as Secretary of the Navy in Grover Cleveland’s administration (1885-9), and he was listed as one of “the 400”.
Put aside Whitney’s 14,000 acre October Mountain Reserve with the 5-acre man-made lake for pleasure boating and the 8-acre game reserve for imported and exotic animals. Put aside the impact of the greatest of the great estates. The sum of smaller Cottages changed the Berkshire landscape.
There is more than one way to count Cottages depending upon how you define a Berkshire Cottage. The definition, from The Berkshire Cottages 1984 is: “a second home with more than twenty rooms on more than thirty acres”. Accepting that definition, there were 30 cottages built in Lenox and Stockbridge between 1880 and 1895. That is two estates per year over fifteen years.

Each of the thirty was massive with multiple buildings constructed on huge land masses some as large as 700 acres. That means that in 15 years between 1880 and 1895, two things changed: up to 21,000 acres in South County were reconfigured, and more important, the economic base shifted from agriculture to servicing the estates.
The farmers watched as the price per acre rose from $5 to $50 and then went higher; some reports allege as high as $1,000 an acre. The farmers sold. They deposited the new-found wealth, and then went to work on the estates.
For more than a hundred years, the “outlanders” who came were some of the richest and most influential among us. The first land owners, the proprietors, were men of substance, favorites of the King or at least favorites of the King’s representatives in the New World. In mid-nineteenth century, the influx of “permanent summer residents” was the cream of Boston society and the literati. In the late nineteenth century, the Cottagers were the nouveau riche of the Gilded Age. These were “the 400” – “the robber barons” — people with deep pockets and a broad reach. The proprietors changed the face of Berkshire as radically in the eighteenth century as the Gilded Age Cottagers did in the nineteenth.
The man who wrote the letter to the editor in 1899 was angry but not necessarily incorrect. There is no doubt those who came from outside changed the Berkshires; the argument centers around the word “ruined.”