Wedged between her parents, each hand attached to one of theirs, Hannah McCormick approached the Oak Bluffs School. She wore a favorite light pink dress and colorful sneakers that lit up pink when she pressed into the toes. Her mother, Kate, slung a Little Mermaid backpack over one shoulder, while her father, Benjamin, carried little Olivia, a preschooler, on his shoulders. Hannah was excited, she said, especially about seeing her friend Eva, who is also a new student in Miss Davey’s kindergarten class.

“We’re very proud,” Mr. McCormick said, looking down at his daughter. “We couldn’t be prouder,” Mrs. McCormick echoed.

They posed for a photo and continued toward the front door, preparing for the momentous occasion. “All right, girls,” Mrs. McCormick said, trying to peel herself away from them so she could make it to Edgartown to open her own classroom there, where she teaches first grade. “Big hugs . . . I’ll call Dad at 12 and see how your day was,” she said.

A few minutes later, veteran seventh grader Matthew Jenkins entered the building, coming off a good summer. The big event? Shaking the hand of Kevin Kline at his uncle’s wedding in upstate New York.

He didn’t look it, but he professed to feeling “some nervousness, like any other student,” on the first day of school, he said. He didn’t know his teacher’s name yet, but was confident he’d find his way, especially since he already knew some of the other kids in the same class.

“It’s a nice place,” he said of the school, which he commutes to from Edgartown each day. “It’s sturdy. They make sure that you learn.”

Matthew and Hannah are two of 392 students enrolled at the Oak Bluffs School this year. Hannah is one of 53 kindergartners.

Two years ago the school was in its fourth year of not meeting the state performance benchmarks. But recently the school has turned itself around and now ranks in the 87th percentile in academic progress.

“The teachers and the students restored good work and it’s showing up in our state benchmarks,” said Principal Richard Smith over the phone last week.

District wide, about 1,422 schoolchildren flood the hallways of the Island’s five elementary schools today, and more than 700 at the high school. An additional 180 students are enrolled at the Martha’s Vineyard Public Charter School in West Tisbury.

Among the crowd of parents that assembled to observe their children line up by teacher and file eagerly into the Oak Bluffs School stood Kimberly Cartwright and Ewell Hopkins, proud parents of Tripp, a sixth grader and avid cyclist, like his parents.

Ms. Cartwright and Mr. Hopkins accompanied their son to school on bikes for the first day of school, but it may be the last escort they perform. “I don’t think we will get many more chances to do this,” Mr. Hopkins said with a sense of nostalgia. Tripp is their third child.

For the rest of the school year, Tripp bikes the two miles from home independently, sometimes catching up with his friends downtown after school. To his parents chagrin, he sometimes leaves the bike without locking it, but so far so good. Tripp’s bike has never been stolen in the four years he has been biking to school.

When Tripp stepped inside the glass school doors, his parents turned to bike to their respective workplaces — Kimberley to her business in West Tisbury and Ewell to Martha’s Vineyard Community Services for a meeting. They’ll bike together up Barnes Road to the roundabout, then part ways.

Inside the lobby area a turtle perched on the highest point of his habitat watched the students march single file down the hallways to their classrooms. Upon entrance, the students scanned the room to find the desks bearing their name and unpacked the contents of a supplies list they’d received over the summer.

Students had almost one extra week of summer this year, due to the timing of Labor Day and Rosh Hashanah, the holiday celebrating the Jewish New Year, which began last Wednesday.

At the regional high school, bleary-eyed students were weighed down by sports gear and book bags full of notebooks and writing implements. Some wore flip flops and shorts despite the autumn chill.

Freshmen, clutching printouts of their schedules, claimed lockers and located their homeroom classrooms. Savanna Aiello of Edgartown said she was quite pleased with her locker real estate. “It’s on the end, not squished between two lockers, and my homeroom is right over there,” she said, pointing to room 201 a few steps away.

Savanna was homeschooled in middle school, so she’s a little nervous to be starting high school, but is looking forward to meeting new people. She is one of more than 185 students in the freshman class, the largest in several years.

Savannah’s first class was Vocational Exploratory, an introductory class to the course offerings in the vocational department. The department has a new head this year in Bob Drobneck, who replaced Jeff Rothwell this summer. He is one of 100 new personnel hired by the school district. Several other employees have switched roles within the district, including West Tisbury’s new principal, Donna Lowell-Bettencourt, who previously served as director of student support services.