The Hill School Celebrates a Century of Community, Character, and Student Confidence

Written by Shayda Windle | Photos by Michael Butcher

Nearly a century ago, in 1926, three visionary families founded The Hill School in Middleburg to provide their children with an education grounded in community values, right in the heart of Hunt Country. The first class of five students met in an upstairs room of what is now King Street Oyster Bar. In its third year, The Hill School settled into its permanent home off South Madison Street. The original campus occupied just half an acre, a modest start compared to the more than 170 acres the school grounds span today. That move marked a defining leap for the young school, both in space and in spirit.

In 1990, Stephen Clark and his daughter Jane Forbes Clark, an influential force in the equestrian community, generously donated 135 acres of land included in the school’s current footprint. Their gift also encompassed three homes and a barn, inspiring administrators to reimagine what the school’s campus could be. The result is a place designed not only for function, but also where students and faculty may live out Hill’s three core values of community, character, and confidence.

“We believe in educating the whole child — intellectually, socially, emotionally, and physically,” Head of School Treavor Lord says. “Hill’s program integrates academics with cocurricular activities like the arts, music, and athletics, ensuring that all students participate in the entire program.”

The campus itself reflects that philosophy with its village-like design, which fosters connection and belonging. Hill maintains a strong partnership with parents and prides itself on knowing every child personally. With a 6-to-1 student-faculty ratio, Hill ensures that every child receives individual attention. “Children are known here,” Lord says. “It feels more like a home than an institution.” 

“Hill’s program integrates academics with cocurricular activities like the arts, music, and athletics, ensuring that all students participate in the entire program.” –Lord

That sense of comfort extends even to the dress code, where students are encouraged to wear their own clothes within modest guidelines rather than formal uniforms. On any given day, students can be seen walking between classrooms, the gym, and lunch across the school’s scenic grounds, breathing fresh air and greeting friends and teachers. The layout encourages interaction among all ages, shaping the confidence they will carry into adult life.

The school also invests deeply in its teachers and provides affordable housing, a tradition that began in 1950 when philanthropist Paul Mellon donated the first faculty home. Today, Hill owns 16 houses throughout Middleburg, a testament to the institution’s roots and continued commitment to those who make the school thrive. 

As Hill approaches its centennial milestone, its leadership team has dedicated the 2025-26 school year to honoring the school’s rich history. “Generations of people have come before us and we are so grateful for what we have,” Lord says. “We need to do our part to make sure the next generations have the same opportunities.”

Three years ago, Hill launched a fundraising campaign to celebrate its first hundred years while securing the next hundred. With an initial goal of $15 million, the campaign surpassed expectations, raising $17.3 million to support faculty housing, need-based scholarships, the annual giving program, and the school’s $20 million endowment.

“We need to do our part to make sure the next generations have the same opportunities.” –Lord 

This summer, Hill purchased an additional 30 acres of land, expanding the vision first imagined by its founders nearly a century ago. As the school approaches its 100th anniversary in 2026, preserving The Hill School’s culture will ensure that the spirit of its founders endures for decades to come. ML

For upcoming centennial celebrations and alumni events, visit hillschool.org.

Published in the December 2025 issue of Middleburg Life.