Backpacks, Big Feelings and Bright Smiles: Wilton Students Return for the First Day of School [PHOTOS]

New backpacks, new sneakers and a wide range of emotions arrived at Wilton Public Schools’ four schools on Tuesday morning, Aug. 25, as students returned for the first day of the 2026-27 school year.

Under a cloud-free sky, faculty and staff greeted children stepping off buses and being dropped off by their parents. Some students moved eagerly toward the doors, already talking with friends. Others approached more cautiously, taking in unfamiliar faces and surroundings. In more than a few cases, the parents appeared more nervous than the children.

District administrators made the rounds from Cider Mill School to Middlebrook Middle School and Wilton High School before ending the morning at Miller-Driscoll Elementary School to welcome students and staff, with Superintendent Kevin Smith moving from building to building.

For Smith, the annual return carries a sense of possibility no matter how many first days he has experienced.

“I love — capital-L love — the ritual of starting a new school year,” Smith said. “It’s an opportunity every single year that we get that most other professions don’t to reset, be a better version of yourself, try some new things, the whole thing.”

A New Welcome at Wilton High School

Greeting students at the front entrance to Wilton High School were junior and senior Link Crew members, the student leaders selected to help freshmen make the transition to high school and find their way around.

Tuesday also marked the first day for some new adult faces at Wilton High School, including new School Resource Officer Bill Whitman, the first-ever Dean of Student Life Michelle Shoop, and new WHS Principal James D’Amico. As he welcomed students into the building, D’Amico said he was excited to start working toward a personal goal for his new role: learning as many student names as possible each day.

First Steps at Miller-Driscoll Elementary

The morning’s final stop was Miller-Driscoll, where the first day of school was also the first day of kindergarten — and, for some children, their first day of school ever.

Staff members helped children find their teachers and where they needed to go as families gathered outside. The scene mixed nervousness with excitement: children compared colorful shoes and new backpacks, met new friends and waited in groups before heading inside.

Kindergarten teacher Sal Giamo was beginning his 25th year in Wilton and his 32nd first day as an educator.

“It’s full of excitement. It’s the new start. It’s an amazing day,” Giamo said. “You only have one chance to make a first impression. That’s what it is — giving these kids a chance to walk in, be really excited about the first day of school and know that’s going to be a wonderful year.”

He called kindergarten “a special place” and described the opportunity to give children their first experience of school as “a blessing that we have.”

Smith said the youngest students give Miller-Driscoll a particular kind of first-day energy.

“When the kids roll in, they’re just ear-to-ear grins,” he said. “There’s just a lot of joy, which I absolutely love. And versions of that are true for all of our schools, but this place in particular, with the fresh faces of our pre-K and kindergarten for the first time, there’s really nothing quite like it.”

Smith recalled former First Selectman Bill Brennan telling him that Miller-Driscoll should be “the gateway to the community” — an idea, Smith said, that has stayed with him through his 13 years of first days in Wilton and continues to be part of his conversations with the school’s staff.

Parents Mark a Milestone, Too

For parents, the morning was its own milestone.

Erin and Mike Forte watched their youngest son’s kindergarten experience begin as he eagerly climbed aboard the bus, and then followed it to Miller-Driscoll.

“He’s not as nervous as we are. He just hopped right on the bus,” Erin Forte said. “But we actually followed the bus here because we wanted to see him get off and go in. But he’s so happy.”

With an older son already at Cider Mill, the Fortes said their previous experience at Miller-Driscoll made them less worried about how their youngest would do. Still, Erin Forte described the moment as “emotional, but happy.”

Joshua Kopac, whose first child Isabelle was also starting kindergarten, was just as impressed by the first-day welcome — and also aware that his own emotions might arrive after hers.

“It’s incredibly organized here, so hats off to the staff. I’m very impressed, but I haven’t fully processed it yet,” Kopac said. Asked how Isabelle handled the morning, he answered simply: “Better than me. Better than my wife.”

Watching families and staff come together, Kopac said the experience “really defines and emphasizes the role of community in Wilton.”

“Just coming here and seeing that and everyone fitting in and it working seamlessly — I’m not inside the building, but I’m really impressed, and it makes me proud to live here,” he said.

The day’s fashion also made an impression. Kopac spotted rainbow unicorn shoes and hockey gear among the sparkles and sequins. “These kids are coming out excited in style,” he said.