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The littlest students lined the first floor hallway May 28, cheering and holding their hands out for, well in most cases, a low five slap as Winchester High School’s soon-to-be graduates poured through the hallways while Kool & the Gang’s “Celebration” played in the background.
It was Senior Walk day, when WHS seniors revisit the places where their education got started, their elementary school, and for roughly a fifth of them that was Ambrose Elementary.
Winchester High School seniors breezed through the hallways revisiting their past while being celebrated by current students at Ambrose Elementary School during the Senior Walk event on May 28, 2026. WINCHESTER NEWS STAFF PHOTOS/CHRIS STEVENS
“Everything looks so small, everything,” said Sloane McCarthy. “The lockers look small.”
“It smelt the same,” said Oscar Cobbold.
After breezing through the hallways, their red graduation gowns fluttering in their wake, the seniors poured out onto their old playground, where they chatted with their former teachers and reminisced about life at Ambrose.
“I remember building fairy tree houses over there,” said Celia Nag, pointing to a corner of the playground.
“It’s so crazy, it doesn’t feel real,” said Zara Poole.
Lila Griffin said she remembers the senior walk when she was an Ambrose Husky.
“We thought they were so old,” she said.
While Celia Nagtegaal said her days at Ambrose felt like a lifetime ago that was not the case for her mother. Janel Nagtegaal said for her, the last 13 years have gone by “in the blink of an eye.”
“She’s my third and my last so it is really emotional,” she said. “They are a really sweet group of kids.”
Michelle McCarthy said her daughter Sloane and Nagtegaal’s daughter, along with Nag, Griffin, Poole, Mya Salyards and Sarah Adams all started Kindergarten together at Ambrose and have been friends and classmates ever since.
It was also a little emotional for Principal Andrea Phelan.
“This is so fun,” she said. “This is the very first class when I became principal, and the first year is always a journey … so this is extra special.”
Cooper Spence said the visit was “pretty cool,” but the feeling was hard to describe.
“It brings up a lot of memories,” he said, adding quickly, “good, all good.”
Chris O’Callahan, who plans to head to Holy Cross in the fall, also got his start on High Street.
He called the Senior Walk “pretty awesome, very nostalgic.” and like McCarthy, said, “it feels the same as I remember it but smaller.”
When asked what he remembered most, he said, without hesitation, “Mrs. (Anne) Brown, she was my second grade teacher. She was the best.”
Cobbold, who said he had a great time at Ambrose, admittedly spending much of it in the principal’s office, also said he had some great teachers, among them Jamie Rankin.
“I loved Oscar,” Rankin said. “I had him during his first year here when he came from England. It was transitional.”
For Rankin, the Senior Walk is always a bit sentimental. She said she recognizes the little ones she had connected with instantly when she sees the young adults, and some it seems have never changed.
“I remember Celia (Torres) as exactly as she is right now,” she said, indicating a girl a few feet away.
It can’t help but make you reflect, she added, and realize that things you might have thought were major issues then weren’t.
“They all turned out OK, in their own unique way,” she said.
Isola Spence echoed that sentiment.
Spence said one greatest gifts of watching your child grow up is realizing that, despite all the changes that come with time, they remain the same person at their core.
“Returning to Ambrose gave me the opportunity to reflect on who Cooper was in elementary school, and even before that, and to see that the qualities that defined him then are still the qualities that define him today,” she said.
She said her son Cooper was always kind, hardworking and curious, was kind and he put effort into everything he did. Over the years, teachers, coaches, and parents have always commented on what a good kid he is, she said.
Clockwise, from top: Winchester High School seniors reminisce with building Educational Support Professional Cathy Leo during the Senior Walk event; Teacher Anne Brown, center, with some of her former students; Once a Husky, always a Husky; Seniors arrive at the place where it all began for them, Ambrose Elementary School. WINCHESTER NEWS STAFF PHOTOS/CHRIS STEVENS Childhood friends, from left, Sloane McCarthy, Lila Griffin, Zara Poole, Celia Nag, Celia Nagtegaal, Mya Salyards and Sarah Adams all started Kindergarten together at Ambrose Elementary School. Students were at the Ambrose on Senior Walk Day, May 28, 2026. COURTESY PHOTO/MICHELLE MCCARTHY
And seeing Brown, who was also Cooper’s second grade teacher, brought up a lot of memories reminding her that the young kid Brown taught is still at heart the same person he is today, she said.
“And seeing Mrs. Brown, brought back so many memories and reminded me that the young kid she taught is, at heart, the same person he is today.
“Watching Cooper return to Ambrose was a powerful reminder that while children grow, mature, and achieve great things, the essence of who they are often remains remarkably unchanged,” Isola Spence said. “Thanks to all the elementary schools for letting this moment happen. It is the highlight of the graduation season.”
The Senior Walk is traditionally the final day of school for Winchester High School seniors. The Class of 2026 will graduate on Friday, June 5, from 6-7:30 p.m., at Knowlton Stadium.
Chris Stevens is an award-winning journalist who has spent 25 years chasing, editing and photographing stories on the North Shore. She is the co-founder and managing editor of Gotta Know Medford.
