The British authority accompanied this expansion but had little weight in the independent and revolutionary-minded Berkshires. Lenox and the neighboring village of Richmond were named for Sir Lennox of Richmond, a member of the House of Lords who argued for greater economic freedoms for the colonies. And it was economic freedoms that were sought in the Berkshires. The rising topography meant falling water, which was harnessed to power the mills. Farms provided grain and wool for these mills. Iron ore deposits quickly fueled the expansionist markets of a post-revolutionary America. All the while the primitive forests of the region fell as the wood provided housing, transport, and fuel through the long and difficult Berkshire winters.

The landscape that was to become Foxhollow was impacted and transformed by these forces. By the mid-nineteenth century it became sheep pasture. But agriculture in the Northeast, rooted as it was in the thin soils of a land once scoured by continental ice sheets, was no competition for the thick, rich soils of the Midwest, now made accessible by the railroads. As farm after farm was abandoned, the great northeastern forest began its recovery. The Berkshires became highly prized for the subtle beauty of its rolling landscape and by the 1870s America's new industrial elite sought large properties for their "cottages." Eventually nearly 80 mansions would be built, laying the foundation for diverse cultural offerings that are the hallmark of the Berkshires today.

George and Marguerite Erskine Westinghouse purchased the high promontory above Laurel Lake and built Erskine Park. Its 120 acres of open lawns, crushed marble roads, engineered ponds and marble bridges, over one mile of iron fence, and nearly 400 white pines were as much of an achievement as the construction of one of the early alternating current power plants. Westinghouse, whose fortune came from the commercialization of electricity, lit up his estate and channeled excess capacity to light the streets of Lenox.

In 1912, both of the Westinghouse's died and the property was sold to Alfred G. Vanderbilt. Mr. Vanderbilt was unfortunately a passenger on the Lusatania, the sinking of which by a German submarine off the southern coast of the British Isles in 1917 ushered the US into WWI. A widow, Mrs. Vanderbilt was an enterprising socialite. She razed the Westinghouse Mansion and built Holmwood, a more modern mansion. It was she who first brought the Boston Symphony Orchestra to the Berkshires, which first performed on the lawns of Foxhollow. This was an historic event that marked the beginning of the summer performance series that was to become the internationally renowned Tanglewood Music Festival.

In 1939, the property was sold to Aileen Farrell and Meigs Fowler, who sought to establish a school for girls. In 1941 the neighboring estate, Edith Wharton's home, was also acquired and used as a dormitory. For nearly forty years Foxhollow Girls School occupied the property. There were many private schools in the Berkshires, and many continue today. However, economic forces shut the doors on several in the early 1970s and Foxhollow was among them. The property was then purchased in 1977 with a different vision, one that was to create a resort and conference center. The Mount was donated by the developer to Shakespeare and Company. The Ponds, a timeshare condominium complex, and the Lakeside Condominiums were developed in the 1980s.

The conference center and resort concept financially collapsed and the property was purchased by Kripalu, the yoga and alternative health center located above Stockbridge Bowl in Lenox. At this time the Apartments were built, though Kripalu had to later sell the property. It was acquired in 1996 by EnlightenNext, which now houses its main administrative facility in the Manor House.