On Tuesday morning, second grader Phoebe Esposito let go of her mother’s hand and ran across the Chilmark School field, her backpack bouncing with each step, to greet her best friend, Virginia Wallace.

Summer had ended and the first day of school was about to begin.

“I missed you,” Phoebe told Virginia as she threw her arms around her friend.

A rite of passage at the Chilmark School: morning drop-off. — Albert O. Fischer

And so it went all over the Island Tuesday, as the new school year started.

At the Chilmark School, which hosts preschoolers to fifth graders, there were tears (mostly parents) and grins (mostly students) at the first-day dropoff.

Susie Bologna’s son, Willie, began fifth grade today and said he is excited to be a leader for the younger kids. Despite his years of experience at the school, his sister Charlotte, who is beginning sixth grade today at the West Tisbury School, promised to show him the ropes.

“I’m gonna coach him through the year,” Charlotte said.

Independence is a full backpack and some friends. — Jonathan Fleischmann

Virginia Barbatti held each of her daughters’ hands as she dropped them off. Valentina and Georgiana are starting kindergarten and preschool, respectively, and Ms. Barbatti said she is excited to return to Chilmark School.

“I love the school and I love the community,” she said.

Sebastian Whitcombe also expressed his gratitude for the preschool as he dropped his three daughters off.

“I’m excited about the first day,” Mr. Whitcombe said. “But I’m most excited to keep the preschool here with the community’s support so that it can continue to support the community.”

At the kindergarten hallway at the Edgartown School. — Jonathan Fleischmann

As he spoke, his eldest daughter, Zaza, was called over by the head of school, Susan Stevens, to act as bell ringer for the day. A smile spread across Zaza’s face as she dropped her mother's hand and ran to the school to assume the responsibility.

Tasher Kisiel, dressed in an oversized baseball cap and a backpack that nearly grazed the sidewalk, entered the building as a kindergartner today after years of playing in the school’s playground. He said he was both nervous and excited to take the big step across the school’s threshold.

At the Edgartown school, which runs from kindergarten to eighth grade, parents and students were shaking off their morning drowsiness. Parent-teacher association president Brooke Leahy said her daughter Maeve is in first grade this year, and her son Michael is in fifth.

“Michael is playing in the gym now because he’s a middle schooler,” she said. “Only fifth grade and up can go into the gym before school... it’s a big deal.”

A little help from a pink teddy bear. — Albert O. Fischer

Despite Michael’s new fifth-grade status, Maeve is convinced that her brother still has plenty of skills to work on — skills that she plans to master in the first grade, including penmanship.

“Michael needs to work on that, too,” she said. “Even though he’s in the fifth grade.”

Nearby, another fifth grader, James Gould-Lamont, was showing off his handwriting with a handmade sign announcing his first day of middle school. He creates a sign each year with his parents for a back-to-school photoshoot.

“Mom definitely facilitates and I cut out the board,” said James’ father, JB Lamont. “James helps color it in.”

Mr. Lamont works from home and he said it can be difficult at times to balance family and work in the summer. But now that James is back in school, Mr. Lamont wishes the season had lasted a little longer.

Gisela Coelho and Renata Nascimento, who both have sons in eighth grade, also longed for a bit more summer. Watching as the boys entered the building for their last first day at the Edgartown School, they clung to each other and wished time would slow down.

When the bell rings there's no turning back. — Mark Alan Lovewell

“[The boys] were born on the same day and we are best friends,” said Ms. Nascimento. “It’s all going too fast. It’s sweet and bitter. Just the other day they were going into kindergarten.”

But for others, time at the Edgartown School is just beginning, and kindergarten teacher Katie Kelly revels in being able to make her students' first day as smooth as possible. Ms. Kelly used to teach first grade, but said that kindergarten is now her forte.

“This is my fifth year teaching kindergarten, and I really just love being able to meet new families and welcome new students here,” she said.

When the school bell rang, parents and children exchanged final hugs and then the kids, clutching their lunch boxes tightly, followed the teachers into their classrooms to start the new school year.

More pictures.