A Trip Inside Timothy Leary's Cultural Crucible and Millbrook's Gilded Age: The Hitchcock Estate
One of the most historically significant, and intriguing properties in New York State is for sale. RI takes an exclusive tour.
The Hitchcock Estate in Millbrook is the most expensive piece of real estate on the market in the region today, on sale for $65 million. It’s most famous for a five-year period in the `60s when LSD pioneer Timothy Leary used the site as his counterculture laboratory. The bucolic and historically significant 2,079-acre property, larger than the Village of Millbrook itself, is saturated with fascinating details and lingering mysteries.
The estate was originally established in the 1890s by industrialist Charles F. Dieterich, who combined four farms and built the original Victorian mansion. He then erected an even more architecturally interesting 10,000-square-foot Italianate guest house in 1914, designed by legendary South Florida architect Addison Mizner. It was there that the lion’s share of the estate’s infamous 20th-century activity took place.
Along with the main houses, the grounds are filled with a number of castle-like structures made of large fieldstone, including the iconic gatehouse near the entrance of the village and the almost medieval-looking cattle farm complex. Exploring deeper, the rolling property contains multiple other homes, an Alpine-themed standalone bowling alley, tennis courts, a pool, two lakes, bridges, walled gardens, and vast expanses of hayfields.
Touring the property with the listing agent, Heather Croner, matriarch of regional high-end real estate, is to be transported to an era of opulence rarely seen in the modern age. The current owners, heirs to the Mellon and Hitchcock banking and energy fortunes, have used the estate with diminishing frequency over the past half century. So, while there is a bit of a vacant, ghostly atmosphere to the place, the lack of occupancy has preserved the historic detail of the site immaculately.
“It’s an incredible property,” says Croner, who became the first Sotheby's agent for Dutchess, Columbia, and Ulster County in 1980. “It just needs to be woken up.”
The guesthouse.
A Vision of the Gilded Age
Dieterich, a German immigrant and a founder of chemical company Union Carbide, established the estate at the height of the Gilded Age, envisioning a sprawling retreat that would showcase European craftsmanship and aristocratic grandeur. His dream led him to Italy, where he recruited artisans who built the estate’s impressive fieldstone walls, turrets, and intricate details. “Mr. Dieterich went to Italy and he brought back a number of artisans, and they settled in Millbrook,” says William M. Hitchcock, current owner of the estate, interviewed from his home in Houston Texas. “A lot of the folks with Italian names in Millbrook have their origins there because of Dieterich’s estate.”
For decades, the property served as a model of Hudson Valley luxury, boasting not only grand architectural features but also fully operational farmland. It later became a private hunting preserve for Standard Oil executives before the Hitchcock family acquired it in 1963.
The Birthplace of Psychedelic Counterculture
Though the estate’s origins lie in a time of note, its legacy is forever tied to 1960s counterculture. Leary and his Harvard research compatriots found a protected base of operations at the estate through the patronage of the Hitchcock siblings—William (or Billy, as he is still known), his twin brother Tommy, and sister Margaret "Peggy" Hitchcock. According to accounts from the time, Peggy was the primary associate of Leary and his colleagues. Today, Billy Hitchcock, 85, says he had little to do with the goings on there, but accounts vary. With his brother and sister now deceased, Hitchcock remains one of the last direct links to the untold history of those heady days. When asked about his experiences from that time, he’s quick to change the subject.
New York State historian Devin Lander has been captivated by the estate for over 20 years. He’s currently writing his doctoral dissertation on the history of the property and is presenting a lecture on its artistic influence at the Millbrook Library March 20. Lander contends that Millbrook, rather than San Francisco’s Haight-Ashbury, was the true birthplace of 1960s psychedelia.
“By late 1963, the Millbrook estate became the center of the burgeoning psychedelic counterculture, just a short two-hour drive from New York City,” Lander says. “Access to artists, writers, and musicians began for Leary and the Harvard group through their relationship with Peggy Hitchcock and Allen Ginsberg, both of whom introduced them to a who’s who of New York’s creative elite.”
The estate became an experimental hub where psychedelics, art, and radical thought intertwined. Ken Kesey and the Merry Pranksters famously visited in 1964, though their wild, performative approach clashed with Leary’s more academic and introspective experiments. The communal atmosphere fostered collaborations between visual artists like USCO, Jackie Cassen, and Don Snyder, alongside writers such as Diane di Prima, Alan Watts, and R. D. Laing. Musicians including Charles Mingus and members of the Grateful Dead were also drawn to the estate, creating an incubator for psychedelic artistic expression.
The main house in the 1960s.
A Legendary Guesthouse
Though the old Victorian famously got painted with a giant face depicting Leary’s idea of the turned-on and tuned-in man, according to most accounts the guest house was the center of the action. “Somebody said it was a copy of Malmaison, which was Napoleon’s wife Josephine’s house after she split from Napoleon,” Hitchcock recalls in his low, gravely, aristocratic voice. “I’ve never seen Malmaison, so I don’t know, but that’s what I was told.” The house's opulent design, featuring palatial painted ceilings and fine inlaid molding, as well as proto-Miami-Art Deco finishings in the bedroom and kitchen wings, were an inspiring backdrop for the visiting celebrities and the intensive research that went on in the grand living space.
“My brother really did a lot of rehabilitation to the property,” Hitchcock recalls. “He spent the time, effort, and money to put this back, best as possible, to what it was.”
The End of an Era
Not everyone welcomed Leary’s Millbrook commune. In 1966, the estate was raided by law enforcement, led by Dutchess County Assistant District Attorney G. Gordon Liddy, who later became infamous for his role in the Watergate scandal. Liddy and his team sought to dismantle what they viewed as an illegal drug operation, though no large-scale LSD production was ever found on-site. The Hitchcocks did ask the group to leave however, as the negative attention was getting too hot. “LSD was never manufactured at Millbrook, as far as I have ever found out,” Lander confirms. “Later in the commune’s existence, introductions were made between West Coast LSD manufacturers and folks on the East Coast, but that was after the estate was closed in early 1968.”
Despite the raid and the eventual dispersal of Leary’s commune, the estate’s reputation as the epicenter of psychedelic exploration persisted. According to Lander, its influence on the broader counterculture movement was profound, providing a space where ideas, art, and alternative lifestyles flourished.
Inside the bowling alley.
Today, the Hitchcock family says it is committed to ensuring the estate’s historical integrity. “We want to see the estate go to someone who understands its value, both architecturally and culturally,” Hitchcock says. “We’re very concerned about how this property would be sold. We want to make the community happy with the eventual sale and ensure it goes to a responsible steward.”
The Hitchcock Estate is not only a historic property but also a living artifact of two vastly different eras of American culture. “I would certainly say that I believe it would qualify for listing on the State and National Register of Historic Places,” Lander says. “The history is deep and rich, and it remains one of the last great estates of its kind."
