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Facing sinking enrollment, Maine's island schools are finding unique solutions to stay afloat

Third grader Isaiah Alley on the ferry from Islesford to Great Cranberry Island, going to school on May 27th, 2026.
Tulley Hescock
/
Maine Public
Third grader Isaiah Alley on the ferry from Islesford to Great Cranberry Island, going to school on May 27, 2026.

Many school districts across the country face declining enrollment, teacher shortages and funding uncertainties. For small island communities off the coast of Maine, these challenges can be even more daunting.

On an island with fewer than 100 year-round residents, declining enrollment can close a school down and force families to relocate.

Every morning, the five students at the Longfellow School on Great Cranberry Island start their day by sitting in a circle and greeting each other over breakfast.

On this day, the circle includes Yvonne Thomas of the Maine Seacoast Mission, which supports schools on these outer islands.

"For year-round island communities, the school is one of the absolute pillars that sort of is linked to a vibrant community, because if you don't have a school, it's hard to have young families," Thomas says.

An alternating approach

Residents of Great Cranberry Island know this all too well because their school was closed for more than 15 years. When it reopened a decade ago, students from both Great Cranberry and Islesford began attending each other's school for two years at a time, connected by the island ferry.

Yvonne Thomas of the Maine Seacoast Mission and Ashley Greenleaf on the ferry between Great and Little Cranberry Islands on their way to the Longfellow School.
Tulley Hescock
/
Maine Public
Yvonne Thomas of the Maine Seacoast Mission and Ashley Greenleaf on the ferry between Great and Little Cranberry Islands on their way to the Longfellow School.

The agreement is designed to ensure both communities can keep their schools and attract new residents like Cranberry Isles teacher, Ashley Greenleaf.

"I grew up really rural, and so I was like, 'I don't want to move to a city. I don't think I would like it. I like small communities,'" Greenleaf says.

Greenleaf says that while she previously taught fourth grade at an elementary school in Jay, teaching on a rural island for the past two years has been a completely different experience.

"The planning is a lot more challenging because I have five students who are in five different grades who are reaching or going towards five different standards every single day," Greenleaf says. "So it's a lot more intensive in that regard, whereas, like, the classroom management is a lot easier, so it's just a lot of give and take, I would say."

Cranberry Isles Teacher Ashley Greenleaf leading the school's morning meeting over breakfast on May 27th, 2026.
Tulley Hescock
/
Maine Public
Cranberry Isles Teacher Ashley Greenleaf leading the school's morning meeting over breakfast on May 27th, 2026.

Teaching Principal Gloria Delsandro spends her days managing those multi-age groups in math. On this day, Delsandro is working with fourth grader Ezra Bunker and Isaiah Alley, a third grader, on some tough word problems involving fractions.

"It's super important to be responsive to the kids that you have in front of you, not just their math skills, but their social emotional needs, and their ... attention spans, and their interest levels," Delsandro says. "So if something's not working, my first reflection is, 'What do I need to do differently, or how do I need to scaffold this, or where is the hang up?' And so I pivot a lot."

Delsandro says these strategies work well in small groups, and the individualized attention may actually offer benefits over traditional classrooms. In fact, Greenleaf says the Cranberry Isles have entered into a contract that would allow mainland students from the Mount Desert Island Regional School System to attend school here on the island.

"We are a really unique school with really unique access to place-based education and to individualized student support that you can't get in a larger classroom, and so we're really welcoming anybody who thinks that their child would benefit from this," Greenleaf says.

Teacher Ashley Greenleaf working with Sixth Grader Ari Pease and Fifth Grader Audrey Sumner on their poetry writing.
Tulley Hescock
/
Maine Public
Teacher Ashley Greenleaf working with Sixth Grader Ari Pease and Fifth Grader Audrey Sumner on their poetry writing.

So far, no one has taken them up on it, but the school will be growing next year with a new pre-K room.

Bunker says he knows both of the pre-k students who are joining next year.

"Theo is my next-door neighbor and Elijah's my brother," Bunker says.

This is the only way the islands have been able to bolster their student numbers. They are hopeful they may be able to draw mainland students in the future, like another island community down the coast in Casco Bay.

Fourth grader Ezra Bunker and Third Grader Isaiah Alley working through some math problems with Teaching Principal Gloria Delsandro.
Tulley Hescock
/
Maine Public
Fourth grader Ezra Bunker and Third Grader Isaiah Alley working through some math problems with Teaching Principal Gloria Delsandro.

Drawing from the mainland

On a clear but brisk sunny spring morning, nine students are lined up to board the ferry from Cousins Island in Yarmouth.

"It's not just like hopping on the bus and getting right to school, especially standing on the dock. That's the hardest part, waiting for the boat to come. It's pretty cold," says Isla Werrell of North Yarmouth.

Werrell has been taking the boat out to the Chebeague Island School, which serves kids from kindergarten through fifth grade. Werrell is a sixth grader, but was accepted for another year.

"I had a hard time with some of the kids at my other school, and I like how it was a lot smaller here, and it was like a lot bigger at my old school. I liked the idea of taking a boat every day, and it was just very different," Werrell says.

Isla Werrell (center) grabbing snack from recess with her brother, Evan at the Chebeague Island School.
Tulley Hescock
/
Maine Public
Isla Werrell (center) grabbing snack from recess with her brother, Evan at the Chebeague Island School.

Mainland families pay $5,000 to send their kids to Chebeague Island school. There's the additional cost of a ferry pass that goes for over $500. But Werrell's mom, Leda Werrell, says it's all worth it, as she felt both her children were getting lost in the larger classroom in the Greely school system, and she wanted something different for them.

"It just appeared to really value allowing the kids to be themselves, and we just wanted to protect their childhood as much as possible, while still giving them the best academic chance," Werrell says.

And Werrell says she felt reassured that the teacher was someone she knew from Isla's kindergarten year on the mainland.

"I don't think I would have stayed in teaching if I didn't make the shift," says Mary Train, who has been teaching for over three decades.

Teacher Mary Train's dog, Bella, resting in the hall of the Chebeague Island School.
Tulley Hescock
/
Maine Public
Teacher Mary Train's dog, Bella, resting in the hall of the Chebeague Island School.

Train says she was starting to fall out of love with the profession before coming out to Chebeague three years ago. She says the island school setting reminds her of her childhood.

"Things like play opportunities, hands-on experiences, a lot of social, just getting used to school, it's almost like there's not time for that anymore, and I think some families were feeling like it was too much for their students," Train says.

Chebeague residents voted to secede from the Cumberland school system nearly 20 years ago. The island school was renovated, but ran at half capacity for some time. Enrollment has since rebounded with 23 kids, including nine from the mainland. That may be in part due to the small class sizes.

"I think that kind of smallness, both in terms of overall school size, as well as just the individual classes, is a real draw for kids who are just, you know, can be overwhelming in the bigger context," Chebeague Superintendent Aaron Townsend says.

Backpacks hung in the main hall of the Chebeague Island School in May 2026.
Tulley Hescock
/
Maine Public
Backpacks hung in the main hall of the Chebeague Island School in May 2026.

Townsend says it helps that the school is so close to a number of large southern Maine communities that it can draw from with only a 20-minute ferry commute.

"Having that cohort of like academic and social peers as a way to sustain the island school, and we're certainly unique, and being able to do it because of the (Chebeague Transportation Co.) ferry connection," Townsend says. "There aren't many of the unbridged islands that have that close a ferry connection, even here within Casco Bay."

Isla Werrell will age out of the Chebeague Island School next year and will have to take classes on the mainland once again. But her mom says Isla's two years on the island have helped her to blossom academically and as a person.

"Had I looked back this time last year, I was very nervous about putting her back in the school system, but she is now more prepared than ever," Leda Werrell says.

Students playing on the playground during recess at the Chebeague Island School.
Tulley Hescock
/
Maine Public
Students playing on the playground during recess at the Chebeague Island School.

And Townsend says the appeal of the program has helped the island maintain enrollments at a consistent level — enough to support its budget and its mission.

Though Chebeague Island is hopeful for its school's future, it's a challenging time for other island communities in Casco Bay. There was talk recently of closing Cliff Island School, which serves just two students. The idea was strongly resisted by residents.

Journalist Madi Smith is Maine Public's Emerging Voices Journalism Fellow this year and is sponsored by support from the Abbagadassett Foundation.
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