As president of the Marblehead High School Class of 2026, Will Cruikshank has spent the year helping lead his classmates toward graduation while reflecting on a high school experience shaped by challenges, friendships and miles of running through town streets.
“Remote learning during COVID and the teacher strike were probably the two biggest challenges,” Cruikshank said. “My class has been fortunate to be a part of some memorable and unique events — a special football game at Fenway, hockey at TD Garden and so many state championships along with some really great musicals over the years.”

A lifelong Marblehead Public Schools student, Cruikshank began kindergarten at Eveleth School before moving to the newly built Glover School.
“Yes — MPS since day one!” he said.
Asked to describe the Class of 2026 in one word, Cruikshank chose “dynamic.”
“We have standout athletes, artists, actors, musicians, bright minds, leaders and creators, but what I admire most is that nobody I know is just one thing,” he said. “Nobody fits into just one category, and I think that says a lot about who we are.”
While Cruikshank has participated in a wide range of activities, he said running had the greatest impact on his high school years.
“Hands down, the highlight of my time at MHS has been running cross country and track under coaches Brian Heenan and Will Herlihy,” he said. “Running made my high school career. Through running, I’ve met the best of friends, and I’ve learned so much about myself. Marblehead is a beautiful place to run, and I think I’ve been down just about every street. I’m grateful that it’s something I can continue for years to come.”
Academically, he said two classes stood out.

“It’s a toss up between AP Art History with Ms. Huller-White and AP Biology with Mr. Heenan,” he said. “Those classes stand out simply because I learned so much. The material was fascinating, and the teachers were excellent. I’d love to study more art history and biology in college.”
This fall, Cruikshank will attend Middlebury College, where he hopes to explore several academic interests before choosing a concentration.
“Their international politics and economics major stands out to me, but honestly, I’m looking to study a wide range of things, including biology and possibly Japanese,” he said.
Beyond school activities, Cruikshank said his work with the youth leadership nonprofit Project 351 has had a lasting influence on him over the past five years.
“One of the coolest parts of it has been getting to work with students from all over Massachusetts, people from towns and backgrounds that are completely different from my own,” he said. “I’ve helped mentor younger ambassadors and worked on outreach projects together, and through all of that I’ve seen how much young people can actually accomplish when they care about the same goal.”
Looking ahead, Cruikshank said he hopes to build a meaningful career while remaining connected to Marblehead.
“I’m not sure yet what I plan to do professionally, but I hope to find a meaningful career where I can make a difference,” he said. “Ultimately, I’d love to work in Boston and end up in Marblehead.”
Cruikshank said he hopes people recognize the strengths of Marblehead’s schools and community.
“I want people to know that I and many of my friends and classmates have done well at MHS,” he said. “Our schools are not perfect — no place is — but I’ve had some amazing teachers and coaches, and I feel prepared for college.”
He also reflected on the connection he feels to the town itself.
“I also feel very much a part of my community, and I’ve loved being able to ride my bike to MHS nearly every day,” he said. “This town is a special place. For years, people have invested in our schools, arts programs, athletic fields, libraries and the spaces where we grew up.”
He added, “As my fellow graduates and I become voters for the first time, I hope we remember that communities stay strong because people choose to participate in them.”
