Ossining High School Welcomes Back Graduates for Alumni Day

On April 11, Ossining High School opened its doors to welcome back former students for Alumni Day. The annual event brought together alumni from a range of graduating classes and career paths to share their post-graduation journeys with current students, offering real-world insight and powerful inspiration.

Throughout the day, alumni visited classrooms, participated in panel discussions, and engaged in candid conversations with students about their time at Ossining High School, the paths they've taken since, and the lessons they’ve learned along the way.

“It’s pretty surreal,” said Jeremy Levine, Class of 2003. “I haven’t been back here since I graduated, so it’s a bit weird—it brings back a lot of memories. It’s great to have those conversations and to be able to share something that can be of value, and something the students find useful.”

The event is designed to help students see the many different shapes success can take—and to reinforce the idea that their time at Ossining can be a strong foundation for whatever future they imagine.

“Being back at Ossining High School is really fun for me,” said Roslyn Wertheimer, Class of 2012. “It’s just really fun and nostalgic, reflecting on the good memories that I have here.”

For nearly a decade, Alumni Day has been organized by Social Studies teacher Barry Jaffess, providing a meaningful opportunity to foster connection across generations.

“It’s one of my favorite days of the year,” said Mr. Jaffess. “I’m asking the alumni to come and give back to our current students—about life, about the ups and downs, how they got to where they are, some of the mistakes they’ve made along the way… you don’t need to know all the answers right away.”

For current students, the chance to hear firsthand from those who once walked the same hallways is both eye-opening and motivating.

“I really appreciate their time and effort—returning to the school and giving their advice on what they are doing, the steps they took to get where they are, and what it looked like in high school for them,” said Cavan Brouder, a member of the Class of 2025.

The day served as a vivid reminder of what’s possible and what’s shared—a common history, a supportive community, and an enduring connection to Ossining High School.

“This event is a powerful reminder of the lasting impact an Ossining education can have,” said Principal Latoya Langley. “Our alumni are doing incredible things in the world, and their stories are inspiring. We want our students to know that the same opportunities are available to them—and that they are part of a proud, supportive Ossining community that extends far beyond graduation.”

Alumni Day is part of the district’s ongoing efforts to strengthen community connections and inspire students through real-world stories and mentorship.