As Jonah Maidoff reflects on his 28 years as a social studies teacher at Martha’s Vineyard Public Charter School and his pending retirement, he says he will miss the school community the most.

“It’s a family and it’s exciting, and it’s close, and it feels very warm,” Mr. Maidoff said. “Our morning meetings are beautiful. And I have relationships with my students that are honest.”

Mr. Maidoff will say goodbye to the classroom and school he has called home for nearly three decades at the end of this school year. Graduation is Sunday, June 2. The charter school opened its doors in West Tisbury in 1996. It currently serves students from kindergarten to 12th grade, focusing on experiential learning, with students, parents and teachers working together to create individual education plans.

Mr. Maidoff has had a front row seat since the beginning, helping the school transform over the years.

“We were a tiny space with 74 students because this was designed as a K-12 school with a mandatory limit of 180 students,” he said. “We’ve expanded out and the playground has changed overtime. But the primary goals have not, which is creating lifelong learners in a sort of democratic system in which students participate in their education.”

Paul Karasik, one of the co-founders of the school, expressed his admiration for Mr. Maidoff.

“One of the great things about Jonah is that he is indefatigable,” Mr. Karasik said. “For a school that prides itself on student-centric learning, Jonah is a tireless advocate for the students. He always puts them first.”

Mr. Maidoff was also known for leading the eight grade trip to Italy each year. — Ray Ewing

Being an educator was not always part of the plan, though.

Initially, Mr. Maidoff pursued a playwriting career while living in New York City, Maine and Los Angeles, as well as a brief stint in property management. But soon after he and his wife Ingrid settled on the Island, Mr. Maidoff heard about plans to open the charter school and decided to enroll at Goddard College to pursue a master’s in education.

He said that readings he did in graduate school, such as one by Parker Palmer, inspired his teaching methodology.

“One of [Palmer’s] foundational ideas is to know each other as you would have them know you,” Mr. Maidoff said. “Having a real responsive relationship with students and other faculty and whatever staff you are working with has been very crucial in my career. The absolutes are a little fuzzy, so engaging with each person from where they are is really important.”

Former student and recent graduate of Amherst College Owen Favreau recalled many memorable moments with Mr. Maidoff as his teacher.

“When I was writing some draft of an essay for [Jonah], he kept giving me comments back and I was getting so frustrated,” Mr. Favreau said. “He pulled me aside and showed me an email from his alma mater, Kenyon, because he had been trying to write something for them and they had been giving comments [back and forth]. He told me it never ends. The editing process lasts forever. Showing me that we were going through the same process was very helpful.”

Mr. Maidoff is also known for leading the eight grade trip to Italy each year, an experience students said was a highlight of their educational experience.

“We traveled around and got to go to the art school that his dad worked at the time,” said former student Kyra Whalen. “It didn’t always necessarily feel like a class trip. I couldn’t imagine going on that kind of trip in eight grade with somebody else. He was well-seasoned and he made the trip really special.”

Ms. Whalen currently works as a voyage guide on the Shenandoah with the Martha’s Vineyard Ocean Academy, educating kids about life at sea, incorporating the lessons Mr. Maidoff taught her.

“I learned a lot about how to be my own person [from Jonah],” Ms. Whalen said.

Mr. Maidoff said he feels that reciprocated energy and respect are key to interacting with students.

“One of the things I’ve discovered is you get back exactly what you put in,” he said. “So if you come into a classroom and you are angry, upset, annoyed, it is reflected back immediately. If you can welcome people into your space with compassion and love and real concern for their good day, it changes the atmosphere.”

Mr. Maidoff’s retirement will have a large impact on the school and community, according to charter school board member and former student Keith Chatinover.

“He’s so important in the charter school community but also to the Vineyard community with all his work with climate and affordable housing,” Mr. Chatinover said. “He is sort of a pillar of a connection to the rest of the island.”

For Mr. Maidoff, his retirement doesn’t signify an ending, but rather a chance to achieve other dreams.

“I really do want to explore more of the world,” he said. “I want to take walks before I can’t and write a lot of poems and plays and teach playwriting and have some more adventures. I want to walk with Ingrid across Portugal. That all seems so exciting to me.”