The Gilded Age in the Berkshires

When the railroad reached the Berkshires in the middle of the eighteen hundreds, it changed the character of Great Barrington almost overnight. Wealthy families from New York and other cities, seeking to escape summer heat and smoke, discovered these cool green hills, and the region became a fashionable resort. The train from Grand Central could carry them here in just a few hours.

Along the valley they built enormous seasonal mansions that they modestly called cottages, though many held dozens of rooms. Grand estates rose in Great Barrington, Stockbridge, and Lenox, surrounded by manicured grounds and sweeping views. One of the earliest was a sprawling estate built by a New York banker named David Leavitt, who also helped develop the local Housatonic Railroad.

The grandest of all was Searles Castle, the dolomite castle built for the widow of a railroad tycoon. This was the Berkshires of the Gilded Age, a playground for the very rich that drew artists, writers, and musicians in their wake. The great fortunes eventually faded, and many of the cottages were lost or converted to schools and institutions.

But the era left a lasting legacy of grand architecture, cultural life, and the enduring reputation of the Berkshires as a summer retreat.