Josh Rilla, one of the most beloved teachers at Williston, will be leaving Williston at the end of the 2024-2025 academic year. For a lot of students, it’s hard to imagine Williston without Rilla.
Rilla graduated from Amherst College in 2006 with a dual major in English and Spanish, and later earned his M.A. in English Literature from Middlebury College in 2016. Prior to Williston, he spent 10 years teaching and coaching at Beaver Country Day School in Newton, Mass. His global experiences include living in Europe and China, where he worked as a professional tennis player, coach, and English teacher.
Rilla came to Williston in 2021 as his wife, an emergency room doctor, accepted a job in Springfield, Mass. While looking at schools in the area, he reconnected with a familiar face.
“Luckily, Mr. [Kyle] Hanford remembered me from graduate school and helped me get to know Williston,” Rilla told The Willistonian. “We were also excited to move back to this area after we both spent four years studying at Amherst College.”
At Williston, Rilla teaches English 9 and ELL, and serves as Head Coach for both the Boys Varsity Tennis and Squash teams. He lives in Hathaway House with his wife and two children and serves as the dorm head.
Kaylee Le, a sophomore from Hanoi, Vietnam, took Rilla’s ELL class freshman year.
“He is very nice and he made the class very engaging,” she said. “He cares about our improvement in English a lot, both inside and outside of the classroom.”
For Kaylee, Rilla’s classroom wasn’t just a place to learn grammar or read some books.
“I could feel comfortable speaking in English in his class, which was something I was really scared at first.,” she said. “He always gave us games during class and he also always tried to make the classroom environment very welcoming so that we could easily ask questions or work in groups.”
Sarah Lucas, a sophomore from Melrose, Mass., also took Rilla’s English class freshman year. She credits Rilla with helping her discover a love for the subject.
“Mr. Rilla really makes you enjoy the subject,” she said. “When I first came to Williston, I hated English class. I remember the first day he said to all of us that ‘my goal is to actually make you guys enjoy English because I know that a lot of people don’t.’ He really helped us understand new writing topics and things like poems. And he made me love English. English is my favorite subject now.”
His fellow English teacher agree with Kaylee too. Jessica Rohan, an English teacher also known as JRoh, respect Rilla’s adaptability and deep care for his students.
“As a teacher, in my understanding, is that he’s a really good listener, and I think that he’s able to cater his instructions to the type of kids there are,” she said. “I think he’s a special teacher who is able to shape and shift throughout the year.”
Rohan described Rilla as a colleague using three words: “welcoming,” “approachable,” and “collaborative.”
“He’s so willing to share anything he has,” she said. “He has really unique background of majoring in Spanish and English and he shared with me a different perspective.”
Rilla’s impact extends far beyond the classroom. As Head Coach for both the Boys Varsity Squash and Tennis team, he has played a crucial role in shaping student athletes on and off the court.
Nevin Conroy, a senior captain of the Boys Varsity Squash team, has had Rilla as his coach for the past three seasons. What stands out to Nevin the most is Rilla’s unwavering positivity.
“The first word that comes to my mind is positive,” he said. “He always got a smile on his face, he is always looking at the positive side even though there is times that seem very tough and there’s a lot of things that are against us, he always finds the light.”
Nevin thinks Rilla has helped him grow both as a squash player and as a leader.
“As a leader, he helped me navigating what it means to be a captain on the team,” he said. “but also, he’s just very great squash player in the first place, so just playing with him, and having him show us the little things he picked up along the way was very helpful.”
The relationship Rilla builds with his players is based on mutual respect.
“I’ve been on teams before where the coach is like a dictator,” he said. “It was kind of intimating to trying to bring up anything. But for Rilla, it almost felt like a friend in a way. There’s things I could bring up, acknowledge that we messed up, and still come back to where we started as a team.”
Though Rilla is leaving Williston, their connection is not ending. Rilla is moving to Portland, Maine, near where Nevin is from.
“He is moving to where I live, so we are going be playing squash over summer and I know I still get to see him,” he said. “But looking at the program, he has helped to bring the program. The program was at rock bottom, I felt like, but he brought it up, so I’m kind of sad that he is not going to bring that energy back next season. And I will miss being in the team with him.”
Boys Varsity Squash team finished second in NEPSAC Class E tournament last trimester.
For some, Rilla was their spirit of their daily lives. Annika Stackmann, a senior proctor at Hathaway House, appreciates the warm and welcoming atmosphere Rilla created in the dorm.
“He makes the dorm feel like a safe and welcoming place where everyone feels supported,” she said. “You can talk to him about anything, and he genuinely listens and cares. He brings a constant sense of energy, fun, and encouragement that really shapes the atmosphere. He was truly the spirit of Hathaway, he was the energy, the joy, and the heart of our community.”
Annika will never forget two bonfires she had this year in the dorm, one at the beginning, and another at the end.
“The first one felt a little awkward as we were all just getting to know each other, but by the time we had the second one, it truly felt like we were a family with Mr. Rilla at the center of it,” she said.
Annika also appreciates Rilla’s respect towards Annika and Francesca Gionfriddo, another junior proctor.
“I also really appreciated the moments when he told Fran and me how much he valued us as proctors,” she said. “Hearing that from him genuinely felt like an honor, and it meant a lot.”
When asked what he will miss the most, Rilla wrote “all of the above.”
“There are small moments, like s’mores night at Hathway or sitting by a fire with my proctors after Phoenix night,” he said. “Those conversations and experiences are unforgettable and only made possible by the fact that we teachers live with the students.”
Rilla is currently looking for a position at schools in and around Portland, Maine.
“I would love to continue teaching 9th grade English, if I get lucky,” he said.
Rilla thinks he will miss his “English office team” the most next year.
“Haas, Loftus, and JRoh. They make every day more colorful,” he said. “And by extension, the whole English Department. The department is chock-full of inspiring writers and parents that have helped me so much over these four years.”
The Williston community will miss Rilla too.
“Every time I see him, he always ask me how my day is and how singing is, and I just feel like I’m gonna miss that a lot,” Sarah said. “Also, [I am going to miss] how he supports everyone here. Even if he didn’t have you in his class, he still reaches out. And I wrote a letter at the end of last year making fun of my grade that he gave me and he still has that letter on his desk, and I think those little things show how sweet he is and I’m gonna miss that a lot.”
“I’ll miss his energy and his ability to bring a smile to the room no matter what kind of day it is,” Annika said. He has a gift for making people feel better, whether it’s through a laugh, a thoughtful conversation, or just his presence. He gives great advice and is someone I really look up to. I’ll also miss how easy it was to talk with him in Spanish, it felt natural and comfortable to switch between languages without any pressure or judgment. And of course, I’ll miss seeing his kids around the dorm, bringing even more life and joy to the space. It was just another example of the warmth and heart he brought to our community.”
