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Alumni Staff Profile: Kathy Flannery

Some 31 years ago, Kathy Flannery was a young mother living in New Paltz. She was part of La Leche league, and through connections there, learned about High Meadow. Fast forward to today, and Kathy is a High Meadow legend.


Kathy in her PreK classroom during the 2018-19 school year.

Back then, as Kathy's son, Conor, got closer to school age, “I didn’t necessarily want to put him into a big, rigid, overwhelming school,” she recalls. With an October birthday, Conor was going to be on the young side for his class, so Kathy called and set up a visit at High Meadow. She spent a morning in the Kindergarten classroom, “and I loved it.”


When Conor joined in 1998, the school had moved to Stone Ridge and was operating out of our current Main Building with a total of about 50 students through 6th grade. Offices were upstairs, with all classrooms downstairs in combined grade-level groups. 


At first, Kathy planned to make a switch to public school after the PreK-Kindergarten room. “At the end of the year, I was really torn,” she recalls. “My husband was saying ‘whatever you think’.” Though not everyone in her circle approved, when Kathy received Conor’s end-of-year report from teachers Barbara Piambino and Jackie Katzen, “that sealed the deal. I remember showing it to everyone, [saying] ‘they know my kid’. We wound up staying for the whole thing.”


A 2002 article about High Meadow's expansion in the Bluestone Press, from Kathy's archives.

Kathy, Conor, and younger brother Tiernan’s time at High Meadow coincided with a period of major growth for the school. “I always think back on this,” Kathy says. “When we came for the first parent meeting, we all met in what’s now the PreK room, and the [all-school] events were in the Dance Studio. It was all woods where the [middle] school is now; that’s where the original PoPo Village was.” 


“At the time, 6th grade was often small,” Kathy explains. “Parents pulled in 5th to avoid starting [public school] in middle school. So it became the plan to try to expand. The way they did it was great. They didn’t just say, ‘now we have 7th and 8th’.” Instead, an existing class led the way year over year, “to keep the culture of the school.” 


Conor’s class followed close behind, on a path that included construction of two new buildings in the decade to come, the Nest and the Performing Arts Center. 


The changes did not come without resistance. “There was a barn where the Nest is,” Kathy says. “A few neighbors fought the building of the Nest. I remember going to a town meeting. But ultimately, the school won. There was one great tree that kids used to be able to sit on. The older kids were upset when that was cleared to build the new building.” The need was clear, though. “It felt like more and more people were hearing about [High Meadow].”


Kathy and her kids in a Bluestone Press article celebrating Mother's Day.

During this time, Kathy’s role at school grew, as well. “I started working doing lunch duty for tuition reduction,” she recalls. “From there, I got to know people and they got to know me. Hope Wootan ran the afterschool program. She needed a day off for some reason, so I started working aftercare one day a week, [then] a couple weeks of camp.”


When Tiernan, Kathy’s younger son, started Kindergarten, “I was offered a position as assistant in PreK and Kindergarten for a year. Then there was an opening in the PreK part time, so I took that.” The next year, circa 2007, she became the lead teacher, and remained in that role until 2020. 


“It was really weird to leave, let me tell you,” Kathy says. She first took time off during the COVID pandemic, then returned for a year before retiring for good. “My last year here, that class was an amazing group of parents and kids,” she recalls. Earlier in her career, when she was dealing with health issues, “the school took up a collection for me and the kids sent home bread and cakes and cards and pictures and I remember feeling, ‘this is not just a school for my kids, this is not just a job’.”


Today, Kathy’s family is thriving. Conor lives in Highland and works with Earth Design Coop, which just bought the dairy farm across from Marbletown Town Park. Tiernan lives in Albany with a position in construction management, the focus of his degree. Though they are not close with their High Meadow classmates, “One of my close friends is someone I met through Tiernan’s class,” Kathy says. She also stays connected via social media: “I get to see Conor’s classmates’ babies!”



“It’s kind of weird, because at this point, I’m not part of the community – only because I’m not here. Up until the pandemic, I felt like there was still – even though the school was bigger and I didn’t know the names of everyone in the school – the community was still here and I felt like that was very obvious. I believe that this is still the case. The teachers all supported each other. I had teachers coming to ask about kids I’d had years earlier; you could fill in blanks for each other about kids’ families, et cetera. I really hope that still exists.” If the reception Kathy receives when she returns for a visit is any indication, it certainly does.

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