After nearly 15 years at the helm of the Chilmark school and 49 years as an educator, head of school Susan Stevens last week announced she plans to retire at the end of the school year.

“I have loved being a part of this community and working with all of your children,” she wrote in a letter to school parents. “I will miss all of the children and their families and I appreciate all the support you have given me.”

The announcement has elicited well-wishes from school committee members and sparked a debate about the future of up-Island school administration.

Susan Stevens keeps her dancing cactus handy. — Jeanna Shepard

The Up-Island Regional School District school committee began talking this week both about the merit of regionalization and whether a single principal should oversee the Chilmark and West Tisbury schools.

Mrs. Stevens’ departure comes at a transitional moment as school enrollment rises, the building undergoes a major renovation and the nonprofit Chilmark preschool, which uses classrooms in the school, looks to construct its own building.

In a tearful interview this week in her office packed with stuffed animals, picture books and colorful troll dolls, Mrs. Stevens reminisced about her years heading up the small, up-Island school.

“I’m going to really miss it,” she said. “I was kind of on the fence about [retiring], and I still get upset because I really enjoy it. But it’s time.”

Mrs. Stevens’ tenure has been marked by a dramatic rise in enrollment, with the student population nearly doubling from 38 students in 2008-2009 to 70 last year, a growth pattern expected to continue.

The school follows a multi-age learning model, where each class combines a younger grade with an older grade. Second and third grade, for example, are paired together. It’s the only school on the Island that follows the method, a legacy of the community school character that’s remained through its recent growth.

“[Mrs. Stevens] has been able to champion a pedagogy, a model that is unique,” said school committee member and former Chilmark school parent Robert Lionette, in an interview.

“To be able to…grow the school, but at the same time stay true to its ethos, its identity, I think it’s really incredible,” Mr. Lionette said. Mrs. Stevens, he added, is currently the longest continuously serving principal on the Island.

The announcement of her retirement earlier in the academic year gives the school district more time to find a replacement, Mr. Lionette said, but the path they will take is still up in the air.

At a meeting of the Up-Island Regional School District school committee Monday to discuss how to replace her, committee members Jeffrey (Skipper) Manter and Alex Salop pushed for an administrative shift to a single principal for both the Chilmark and West Tisbury schools, with assistant principals at both sites.

“I think would it be a more efficient operation [and] a more regional operation … if one principal led both schools,” said Mr. Manter.

Susan Stevens checks in on some students at the Chilmark school. — Jeanna Shepard

Superintendent Richard Smith advised against the proposal, saying it would steeply increase the administrative workload for West Tisbury principal Donna Lowell-Bettencourt.

“I worry about the capacity issue … if we look at a single-principal model,” Mr. Smith said.

The committee voted to continue discussing the administrative model, budgeting and hiring implications at a meeting on Oct. 19.

While that plays out, Mrs. Stevens says she is focused on savoring her final year with the students.

“I just really like the kids…I’m here because they don’t walk by without giving me a hug in the morning,” she said.

Coming to the Chilmark school was something of a culture shock for Mrs. Stevens, who began teaching in 1976 in Florida and seldom encountered classes with fewer than 35 students. It was there that she met her husband, former Edgartown school principal and current schools assistant superintendent John Stevens.

The couple were longtime seasonal residents before Mr. Stevens, who grew up on the Island, returned to become the school principal in his hometown. Soon after, Mrs. Stevens followed, to head up a school that was much smaller than she was accustomed to.

“I was coming from a school of 3,500,” she said. “I remember the first day I came [to Chilmark], and they all were having lunch on the floor in the big room, and that was very different.”

But with a background in teaching and guidance counseling, Mrs. Stevens quickly took to the school’s atmosphere.

“I realized how they were building community, and that was really just as important, because then [the students] worked together better in all the academic tasks,” she said.

Her office is a testament to her hands-on approach, filled with toys and games. A mechanical, dancing plush cactus is among the favorite attractions, and kids often stop by to see Mrs. Stevens perform magic tricks.

“I have a couple students who if they are having a rough day, or they need to take a break, they can come sit in here and play,” she said. “They know it’s a place that they’re safe.”

Aside from cultivating those relationships, Mrs. Stevens has also spent many hours getting to know the building itself as the school has undertaken several upgrades.

“There’s been a couple of times when I’ve been asked to describe exactly what’s going on with the HVAC system,” she said. “That’s a little frustrating…but all principals are in that situation.”

But throughout years of the sometimes-contentious construction process, Mrs. Stevens said, her focus has remained on the students. As she steps back into retirement next year, she is still not sure exactly how she will spend her time.

“I’m not sure yet. I really don’t know,” she said, but added that, on a small Island, she won’t be far away. “They’ll be able to find me.”

Louisa Hufstader contributed to this report.