The pencils are sharpened, the buses are ready to roll and teachers returned to their classrooms this week to prepare for the arrival of the new school year.
Across the Island, the five elementary schools, regional high school and public charter school will all welcome back students on Tuesday. When they arrive, they will be greeted by new staff, new infrastructure and new strategies for keeping students educated.
Jaime Curley is one of the new faces. Ms. Curley, the former assistant superintendent at the Old Rochester school district in Plymouth County, was hired in February to replace the retiring superintendent Richard Smith.
Ms. Curley started in July, and said in an interview this week that she was ready for the school year to start.
“I was so excited when I got appointed to the position back in February, and then July 1st could not come soon enough,” she said at the administrative offices in Vineyard Haven. “I couldn’t wait to get in here and meet people and just be a part of the community.”
In addition to Ms. Curley, the regional high school ushered in a new principal, Bryan Lombardi, and the Martha’s Vineyard Public Charter School hired Christopher Nace to take the reins from former school director Peter Steedman.
All three said they are listening to the community during their first year to understand how the Vineyard approaches education.
“All schools are unique to their communities,” said Mr. Lombardi, who came to the Island after serving as the principal of Stoneham High School. “My job is to come in and learn about that.”
Each of the seven Vineyard schools are expecting changes at the start of the new year, whether it be from fluctuating enrollment to new programs.
In Tisbury, principal John Custer said he has one of the largest kindergarten classes in recent memory with 40 students. That has forced the school to increase the number of kindergarten classrooms, a rarity during Mr. Custer’s nearly two decades as principal.
“We will have three kindergarten homerooms,” he said. “This is only the second time we’ve had to carve out a third section for any grade level.”
After years of teaching students in trailers, the Tisbury school staff has started to get comfortable in their new school building, which was totally redone and reopened in 2024.
“We are going into our third year with this beautiful building,” Mr. Custer said. “It feels really good to be settled.”
Infrastructure improvements is a common thread across many schools.
The Chilmark School staff are ready to move back to their well water after PFAS was discovered in the water in 2025. The school had been running on bottled water ever since, but had a new filtration system installed over the summer that was inspected by the state last week. The Massachusetts Department of Environmental Protection still needs a final sign off, but it should be ready for the beginning of the year, said principal Kate Squire.
The Chilmark Preschool also opened its new school, which has freed up space within the elementary school.
The Martha’s Vineyard Public Charter School has added a new project room, a 224-square foot space, and new offices to deal with a space crunch at the West Tisbury campus.
One potential use for the project room could be as a practice area for the strings music program, which currently rehearses outside.
“They will give us more flexibility to do the things we know we need to do,” said Mr. Nace.
In Oak Bluffs, principal Jeremy Light was celebrating the installation of a new boiler. While that may not sound exciting, Mr. Light said getting the essentials of a building right helps education overall.
“One room would be 60 degrees and the other would be 80,” he said.
Mr. Light was also eager to welcome the school’s first ever resource officer, Julia Levesque. A police officer with Oak Bluffs, Ms. Levesque will be in the school full-time. Mr. Light credited the addition to Oak Bluffs police Chief Jonathan Searle.
Ms. Levesque will be at the school for safety in the building, as well as educating students, according to Mr. Light.
“I plan to have her in the classrooms to talk bike safety and pedestrian safety,” he said. “Having her here to educate them, that’s something that I really hope helps our community.”
Other principals also highlighted new hires. Sarah Karlinsky is starting out as the new librarian at the West Tisbury School, and is bringing a redesign to the library there. Dr. Scott Goldin is the Edgartown School’s first director of student success. In the new position, Mr. Goldin will support teachers and students to ensure students excel in school, whether it be academically or socially.
“It supports students to be their best selves,” said principal Kate Campbell.
Several of the educators who spoke with the Gazette said that programming changes are also on the horizon.
Chilmark, for instance, is moving away from its traditional multi-grade classrooms this year — a decision which caused some concern from some members of the community.
Only kindergarten and 5th grade were single grade classrooms in recent years, but that practice is now extending to all grades with educational standards becoming stricter and enrollment up. Students would often have to shuffle around for English and math class, leaving students unsettled during the day.
“We are really going to be able to focus on extending time on learning,” Ms. Squire said. “It was becoming performative and that didn’t feel like it was right for the kids.”
The Chilmark School is also bringing Wampanoag Tribe of Gay Head (Aquinnah) education department director Brad Lopes to help integrate Indigenous history into the curriculum there.
Schools are also rethinking how they deploy technology in the classroom. Educators said that the use of computers and other devices during the school day has become so ubiquitous that many are considering ways to dial it back.
The regional high school is continuing its “Away for the Day” policy where students’ phones are secured in locked pouches. At the West Tisbury School, teachers have stopped giving students their own computers for classes, and the school is adding more programs that allow students to choose what they do during down times during the day.
“We have been really focusing on how to look at more opportunities to share things they want to do and do that in the school day,” said principal Donna Lowell-Bettencourt.
The idea is that students will be more likely to interact with each other, and less with screens.
“One of the things we are going to do is move away from screens as much as we can,” Ms. Lowell-Bettencourt said. “It’s really an attempt to get back to more face to face, pen and pencil.”
The elementary schools are also all now using the same English curriculum, with students in all the towns reading the same materials. This was enacted last year, according to Superintendent Curley, in an effort to standardize and help students who move from school to school.
“We’re excited to carry that forward into year two,” she said.
The biggest change for any of the schools is one that won’t be felt this year, but will be in the planning stages.
Officials are working on nailing down the plans for an overhaul of the regional high school building after voters approved $333.5 million in June.
Bryan Lombardi, who went through the school building process when he was at Stoneham, said that construction could start in the spring of 2027. He said he was determined to help students thrive, even as the building is being torn down and then rebuilt around them.
“They are laying out the phases and what they are trying to do is be as least disruptive to our environment as possible,” Mr. Lombardi said.
This article appears in September 4, 2026.
So delighted to hear the positive news not only about the new spaces but most importantly, the move away from screens and back to paper and pencil tasks! I have been in private practice on the island since I returned to live full-time in June 2017. With that, has come the distinct privilege of working with island learners and during the summer, learners from other states.
Always, we work with classic workbooks and pencils. Manuscript and cursive handwriting are critical elements in the intervention as we work to build language skills for both spoken and written purposes. Our personal ‘art’, our handwriting, is a part of our identity and importantly, a brain mechanism that we use for building language skills!!
Less screen time? More time to build social interaction, learning to look at the world around us and yes, ultimately critical thinking. Thank you for this ‘new’ agenda!
Amen, and it has been proven that information is more efficiently retained when a student writes with pencil and paper rather than with a computer. Thank you.