On Monday, February 9th, at the Winter Park, Florida campus of the 2025 $1 million Yass Prize winner, Chesterton School Network, the 2026 Yass Prize competition was officially launched!
Known as the “Pulitzer of Education Innovation,” the Yass Prize rewards and celebrates schools and organizations delivering a Sustainable, Transformational, Outstanding, and Permissionless – or STOP – education. This announcement launches a national call for new applicants to vie for the 2026 $1 million Yass Prize.
The announcement occurred during the kick-off of the annual Yass Prize Roadshow for Opportunity, where team members and alumni gather to visit the most recent awardees of the Prize and STOP Awards Initiative in action.
Among those who traveled to the Sunshine state from across the country to see firsthand their peers’ schools in action were 2025 Yass Prize Finalists:
Jeff Skowronek of Pepin Academies, Mimosa Jones Tunney of School House, Tiffany Thenor of WonderHere, and Mercedes Grant of Path of Life Learning , who all shared powerful updates and reflections on their work and the collaboration happening amidst the Yass Prize cohorts.
But the heart of the visit was celebrating and recognizing Chesterton Schools Network for its commitment to the STOP principles. Chesterton is a rapidly growing national network of classically Catholic high schools rooted in the belief that education should form the whole person – morally, spiritually, socially, and academically. Built on the wisdom of G.K. Chesterton and the tradition of a content-rich liberal arts education, Chesterton Academies are committed to “getting back to the soul of education,” as President Dale Ahlquist describes it – passing down truth and tradition from one generation to the next and fostering intellectual curiosity grounded in timeless principles.
“Students read the Iliad “because all of life is a battle” the Odyssey “because all of life is a journey”, and Dickens “because all of life is a great expectation.”
At the heart of Chesterton’s model is an integrated curriculum that connects literature, philosophy, history, science, theology, and the arts into one seamless tapestry. Students learn not as passive recipients but as active thinkers engaging with fundamental questions of life. As Executive Director Emily de Rotstein shared, “Students are essentially getting a four-year liberal arts college education in high school.”
We witnessed high school scholars debating A Man for All Seasons, explaining their science project on whether plants can grow on the moon, and ending the day singing Salve Regina confidently with the school choir – a glimpse into the holistic experience that defines Chesterton’s approach. “Teenagers love asking why,” Principal Jim Hickel shared. “We give them the why here.”
Founded in 2008 in the Twin Cities, Chesterton’s growth is powered by a parent-led grassroots movement. “You can never underestimate the power of parents,” shared de Rotstein.
Chesterton parents today remain deeply involved – from launching academies in their communities to sustaining them with unwavering commitment.
Brandon Vogt – Founder, Board Chair, bestselling author, and parent – emphasized, “The Network not only helps people open schools, but open them with a high level of expertise, and that’s why it’s been so successful.” The alignment of network guidance, parental leadership, and Florida’s robust school choice policies has allowed Chesterton Academy of Orlando to thrive. “School choice enabled us to come and to succeed,” Vogt noted, as evidenced by the 4 Chesterton locations in Florida, with 4 more opening soon.
The Chesterton Schools Network has ambitious plans for the future, in part thanks to the recognition of winning the $1 million Yass Prize this past December. They have seventy schools nationwide, 18 new schools slated to open in 2027, and an additional 30 schools that are in development, with a bold vision to grow from 100 to 1,000 schools worldwide by 2040. “We are grateful, energized, ready,” de Rotstein shared. “The Yass Prize is not only the recognition – it is the fuel.”
To learn more about the Yass Prize and apply, visit YassPrize.org. And be sure to follow along for our next Roadshow stop – our 2025 Yass Prize Finalist – WonderHere in Lakeland, Florida!
To enjoy more photos from this visit, please see the entire gallery here.