The gatehouse that visitors to the Hitchcock Estate, located at Route 44 and Franklin Avenue, Millbrook and leased by Timothy Leary, passed as they entered the realm of psychedelic possibilities.
When author Tonia Shoumatoff attended a Millbrook Historical Society (MHS) presentation May 16, 2019, about psychedelic guru Timothy Leary, it made a big impression on her.
In fact, as she related at another MHS presentation Thursday, Jan. 18, 2024, she told the audience that the presentation — made by New York State Historian Devon Lander about the life and times of Millbrook in the Timothy Leary era — inspired the second part of her latest book, “Historic Tales of the Hudson Valley: Life at the End of the Line,” which came out in July 2023.
Shoumatoff told the by now well-known story: Leary had started on the Psilocybin Project while at Harvard University, researching the use of psychedelic drugs and their potential for use in the treatment of mental health issues. Through meetings with different people, and some haphazard events, the Project devolved from there, into something not that scientific and not widely regarded as serious research.
But was Millbrook an odd choice for Leary? No, said Shoumatoff. This area has been a home, a birthplace, for many innovative projects, she said, naming some of the many religious orders that found homes here, such as the Millerites, the Shakers and the Quakers.
Perhaps the beautiful landscape lends itself to solitude, or that the closeness to nature fosters a closeness to prayer. Whatever the reason, Dutchess County, in particular its northeastern corner, has attracted, many peculiar utopian and religious groups.
She read an excerpt from her book:
“A Victorian utopian community claiming to see fairies settled in Wassaic, attracting Japanese samurai and remaking the townscape of Amenia. An early version of the “Borscht Belt” began on the shores of Lake Amenia, where a once-thriving resort community vanished along with the lake itself.
Amidst a crisis of dwindling membership, the NAACP was brought together at major conferences held at Amenia’s Troutbeck estate, then owned by Joel Spingarn, the organization’s first Jewish president. Young graduates from the Rhode Island School of design and other art schools launched the Wassaic Project, a festival and art residency using a converted agricultural grain elevator as their venue.”
Leary and fellow Harvard professor Richard Alpert started the Psilocybin Project in 1960, but by 1962, the project had gotten bad reviews from others at Harvard; Alpert was accused of having given psilocybin to an undergraduate, and both were fired from the university.
In 1963, the Hitchcock brothers invited Leary to rent the estate, consisting of 2,300 acres, for $1 per year, and he lived and entertained there for the next five years. The estate is at Route 44 and Franklin Avenue, and the impressive gate house is still there.
They entertained an assortment of hirsute celebrities such as Allen Ginsberg, R.D. Laing, and Charles Mingus.
Depending on who you’re talking to, the estate is remembered for its endless parties and all kinds of happenings; others say it was all research and science.
At any rate, after five years and a lot of FBI raids, Leary and his entourage left, and we can imagine that Millbrook gave a collective sigh of relief.
John Flanagan, a member of the MHS, was a young reporter at the time for The Poughkeepsie Journal. He related a story involving Leary and Rosemary Woodruff, whom Leary married at the estate in 1967:
Sent by the paper to cover the event, Flanagan was with fellow a fellow journalist when Woodruff began talking to them. Realizing that Flanagan was from The Poughkeepsie Journal, which continuously made negative comments about Leary through its editorials, she flew into a rage and insisted he be thrown out.
When Leary resisted, she said she wouldn’t get married as long as Flanagan was present. He went off to another part of the estate, the marriage was conducted, and Flanagan got his pictures and story through his friend. Because the Journal was a feed for the Associated Press, it ran in newspapers across the world. Begged Flanagan, “Just don’t use my name! I have to live in Millbrook.”
Many people still remember that time in the ’60s when Millbrook became known for its infamous inhabitant. But like all things in the past, memories soften a bit with age, and become substance for historical society presentations.
Shoumatoff was entertaining, at times funny, but still got the message across that however serene the scenery may be, there is always something interesting festering beneath the surface, and even Millbrook has some wild tales to tell.
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Students dressed in neon lined the soccer field for senior night under the lights on Thursday, Oct. 16. The game against Lakeview was the last in a series of competitions Thursday night in celebration of Homecoming 2025.
As homecoming week reaches its end and fall sports finish out the season, an air of school spirit and student participation seems to be on the rise across Housatonic Valley Regional High School.
But what can be attributed to this sudden peak of student interest? That’s largely due to SGA. Also known as the Student Government Association, SGA has dedicated itself to creating events to bring the entire student body together. This year, they decided to change some traditions.
Spirit week from Oct. 14-17 was unlike those of the previous years. From wearing Housatonic merch to Boomer vs Baby day, this year’s spirit week held a little friendly competition to see which grade could participate the most.
“I think that students are bored of the same old activities and events, so it’s good to switch things up even slightly to incentivize interest within students,” said SGA president and senior Mollie Ford. “Plus the point system is super beneficial because it gives students a reason to participate.”
The school spirit sentiment can be seen outside of just the school. Senior Simon Markow is known for his photography throughout the community, and has dedicated time to help Housy sports teams’ social media posts.
“Since I’ve started photography, I think school attendance [at sports games] has gone up,” Markow said. “I feel this year, students will be more aware of games and are more likely to be at the games.”
Whether it’s a pink-out volleyball game or an under the lights soccer match, it’s likely you’ll see some familiar faces.
Social media has played a large role in this over the years. Almost every student organization at Housatonic has an Instagram account, and it’s helped reach students more efficiently than a poster or email would.
“The increase of social media use, with the help from me but as well as the teams themselves has definitely increased student interest,” Markow said. “With Housy teams posting more about their upcoming games, and my help showing the cool goals, spikes, or touchdowns, it’s enlightened students to watch the games themselves.”
In a small school, promoting pride has proven to be a challenge. But this year’s senior class has made some adjustments in the hopes to change that.
“The SGA community has spent the last few years really focusing on student participation, because we think it’s the students who contribute to a better climate,” Ford said. While Housatonic’s student body may be small in size, it seems they certainly aren’t small in spirit.
The weekend of Homecoming at HVRHS was packed with events including rival games under the lights, senior night, and a new take on Homecoming that moves it outside — and it wouldn’t have been possible without the students of Housatonic.
Orchestrating was no easy feat, especially considering much of the work was left up to the students.
Historically, HVRHS has hosted night games for boys and girls soccer and the GNH football team, but when members of the soccer team asked the athletic director, Anne MacNeil, she left it up to the students to acquire the lights necessary to host a night game.
“I said, ‘Hey, if you can find the lights, we can make it happen,’” MacNeil said. “I usually take control of it, but I really wanted to have the teams have the initiative and take responsibility for it. I think by having them do that, they have a lot more invested in it.”
Finding lights for the game was a challenge in and of itself, and it fell on the students, parents, and alumni to come together if there was to be a night game at all.
Luckily for the players, Patricia and Dino Labbadia, parents of senior Anthony Labaddia, were able to amass the support of the community and get all the necessary equipment donated for the night game.
“We’re fortunate with our communities. Our parents know people in communities and they were able to ask… [and] find the resources,” MacNeil said. “We’ve got a great senior group and senior parent group who have really taken charge … and really made the whole season possible.”
In the end, the night came together spectacularly, and the senior ceremonies, rivalry games, and nighttime fixtures made for a memorable night on the day before Homecoming.
The action began at 4 p.m. Thursday, when the JV Girls Volleyball team played rivals Lakeview High School at home.
At 4:30, the middle school boys soccer team as well as the cross country team faced Northwestern at Housatonic’s lower field and cross country course respectively. Also at 4:30, the JV boys soccer team took on rival Lakeview at Housatonic’s upper field.
At 5:15, the girls varsity volleyball team honored their seniors at Housatonic’s Senior Night ceremony, including captains Katie Crane and Victoria Brooks, before an intense match against Lakeview.
At 6:15, the boys varsity soccer team honored their seniors, including captains Everet Belancik and Abram Kirshner, before kicking off under the lights at Housatonic’s upper field against the Bobcats.
Friday night changes
Typically, Homecoming is hosted in the cafeteria with a DJ and the entire room open as a dance floor. Dancing is the main event, with a small photo op stationed next to one of the exits.
The typical formal dance filled with LED lights and glitter looked a bit different this year. For the HVRHS 2025 Homecoming, the activities all took place outside. There was a large bonfire for students to hang around, a tented area perfect for dancing, and lawn games to play.
The inspiration for this change comes from the Homecoming hosted during the COVID-19 social distancing restrictions put into place at the time. Senior class President Madison Graney said “Other years passed, graduating classes really enjoyed it and we wanted to give it a try.”
Although the theme of Homecoming remains the same, new tasks came in preparation for the event. Including the Bonfire “adds a whole new component,” Graney said. “[We] have to contact the fire department to ensure that the bonfire is being contained.” Hosting the dance outside also demanded “more preparation the day before … set up the tents and make sure it’s a safe and fun space for everyone to enjoy.”
Opinions about Homecoming’s new look vary amongst the student body, with some excited for change and others comfortable with the familiarity of an inside dance. Alexa Meach, an HVRHS senior, expressed that “Everyone that I’ve talked to’s plan is to get dressed up, take photos, and then change into more comfortable clothes because it’s going to be freezing. I feel like we could have had a different event for the bonfire. I think they could have been two separate events.”
Graney said the change is “A really great way to change up the tradition ... [and] another good way to get to know your peers and your teachers and interact with the student body all at once.”
