In 1958, author and historian George P. Swetnam opened “So Stand Throughout the Years: A History of Shady Side Academy 1883–1958” by declaring, “A school such as Shady Side Academy is like a tree which rises from small beginnings and grows throughout the years, in good seasons and bad, in tempest and sunshine.”

Sixty-eight years later, President Bart Griffith ’93 P’28 extended the metaphor while speaking at the ribbon cutting for Rockwell Middle School. “Just behind me — outside the north façade of Rockwell Middle School — stands one of the Academy’s oldest trees, planted in the early years of this campus. For more than a century, through countless seasons and changes at the Academy, it has taken root and offered shade,” Griffith said. “Shady Side itself has grown in much the same way. Each generation adds something to the whole: a decision, a building, a standard held firm. What we do here lasts longer than we do, and that is precisely why it matters.”

If Shady Side Academy is like a tree, it continues to flourish because its stewards — administrators, faculty, students, alumni, and staff — remain attentive to its roots and the many years of experience built into its widening trunk.

In a speech given during an assembly before the first day of classes at Rockwell Middle School, Head of School Michelle Merson P’28 reflected on the occasion’s significance in a long history of growth and purpose. She told excited students, “You are standing as part of Shady Side Academy — a school whose story spans more than one hundred and forty years, built by generations of students, teachers, and families who once stood exactly where you are now, ready to take the next step in their own journey of discovery and growth.”

Reuniting with Our Roots

When Rockwell Middle School officially opened its doors on Tuesday, January 6, 2026, a new chapter in Shady Side’s storied history began. While the building was constructed with an eye toward the future, its presence on the Upper School Campus represents a reunification that honors Shady Side’s history.

Shady Side’s first middle school and senior school-aged students were taught together, not just on one campus, but in one room. In 1883, head of school Professor W. R. Crabbe grouped roughly 16 boys ages 12 to 18 into grades seven through 12 and taught them in a one-room schoolhouse on Aiken Avenue. With a single teacher at the helm, the students collaborated across grades.

After a successful first year, the small school building got an addition that allowed room for another teacher and up to 35 students in grades seven through 12. Shady Side moved to a property on Ellsworth and Morewood Avenues in 1885, and by 1889, the School’s imprint included a gymnasium, two additional classrooms, and a large study room available to members of every grade in the School. In addition to opportunities to study together, that same room also provided space for younger students to observe and learn from their older peers. Carl D. Schultz, Class of 1903, was quoted in “So Stand Throughout the Years”, “Each Friday afternoon, as I remember, there was a meeting in the Study Hall. At this meeting, each boy, at least once in the year, was required to appear on the stage and either recite or be in a play.”

Shady Side’s residence on Morewood and Ellsworth Avenues sufficed through the first decade of the 1900s; a Junior School adding grades one through six also opened on the property in 1909. Crabbe’s successor, Luther Bentley Adams, led the School during a financial crisis, war, and flu and measles epidemics. He suggested Shady Side should consider a move to the country and adopt boarding practices for grades seven through 12 if it were to continue to grow and flourish. Trustee Wallace H. Rowe, founder of the Pittsburgh Steel Company, agreed with this vision. In early 1916, he climbed a hill in Fox Chapel with his two young granddaughters and admired an expansive view of quiet farmland. He purchased 125 acres and issued a challenge to the board: if they raised $500,000, he would give the property to Shady Side Academy. 

“Rowe, along with other early stewards of this campus, made a practical bet with moral stakes,” Griffith says. “They believed that Pittsburgh — then in its boom years, while still restless and unfinished — was worthy of a school that would do more than instruct, a school whose very design would reflect our city’s enduring values and help shape intellect, character,
and leadership.”  

After Rowe’s death in 1919, his wife followed through on her husband’s plans to hand over the deed to the Fox Chapel farmland. In May 1922, Rowe Hall’s cornerstone was laid. That fall, students in grades seven through 12 moved to the Fox Chapel campus, while first through sixth graders occupied the Junior School. In 1940, when Shady Side’s Junior School merged with The Arnold School, a smaller school, seventh grade students moved to the Junior School’s new building on Braddock Avenue along with kindergartners through sixth graders.

By 1930, with its dust long since settled and its grounds covered in lush grass, Shady Side’s Senior School had “some fourteen buildings, two main athletic fields, eight tennis courts, a soccer field, two practice playing fields, a hockey pond, and a nine-hole golf course,” Shady Side’s third headmaster, Harold Nomer, told “Fox Chapel Magazine.” He boasted of the School’s athletic requirement for all students in grades seven through 12, and noted that two-thirds of the student body were boarders residing in “the four dormitories, named Ellsworth, Morewood, Aiken, and Bayard, after the streets closely connected with the early history of the School.”
 

Rockwell's Moment in History

The benefits of building a school meant for today’s middle school students are clear. “Rockwell Middle School is designed for how middle schoolers actually learn and how teachers actually teach,” says Griffith. “It is a working place, built with intention, flexibility, and pride.” Adaptable classrooms, collaborative learning hubs, think tanks, a makerspace, and intentionally-designed common spaces are certainly highlights of the new space. But just as importantly, the new building tightens the connective tissue that makes Shady Side a collaborative community.

For the first time since 1922, Middle School and Senior School students encompassing grades six through twelve are mere steps from one another. Their presence together on the unified Upper School Campus has faculty and staff energized by opportunities for connection. Senior School Dean of Student Life Chad Green P’19,’22,’24 and Amy Hurtuk P’39, Middle School Dean of Students, are already collaborating with students to build connections. Shortly after Rockwell’s opening, the Senior School Speech and Debate team led a Middle School assembly. Other students have expressed interest in exploring academic, athletic, and social mentorship opportunities. 

“So much of what we learn in schools we learn by virtue of our interactions with others,” says Head of Senior School Andrew Prince. “Community and connection matter, and bringing students into closer proximity creates a meaningful opportunity for older students to take responsibility for those coming up behind them.”

Preserving the Past for the Future

When Middle School Social Studies & History Teacher Kaitlyn Willesen first joined the faculty at Shady Side Academy two years ago, she was thrilled to learn that her orientation included a crash course in Shady Side’s history.

“I was fascinated by how much the School knows about its own history, and delighted that they want the teachers and the community to engage with that history,” she says.

Knowing that she and her students would move from Benedum Hall to Rockwell Middle School in the near future, Willesen felt called to help preserve this period in history. She suggested an archive committee and encountered a group of students who were eager to join. “When this project started, I thought we would focus on getting pictures of the architecture, but as students talked to their parents, several of whom went to the Middle School too, they told me they wanted to focus more on what the building meant to them and try to preserve the story of how our school community has grown and changed,” she says.

“We realized the archive committee should be more than just documenting architecture. We wanted to capture the actual spirit of the school,” says Sumukh Bajpai ’30, who was a committee co-chair in his eighth grade year. Fellow co-chair Dylan Kushner ’30 says the committee spent the last year recreating old photos that have lined the walls of Benedum Hall for generations and distributing questionnaires to record Middle School student’s memories of Benedum Hall, predictions for Rockwell Middle School, and reactions following the move. “My favorite part was restating a student’s predictions about Rockwell and asking them how accurate it was after we moved in,” Kushner says.

“Through this project, these students are learning that history isn’t just big events; it’s everyday experiences that get remembered many years later,” Willesen says. The process is particularly special for students like Kushner, whose dad Jason Kushner ’89 also attended the Middle School. “Traditions were formed here. Identities were formed. When Dylan talks to his dad about the school, his dad gets to tell him what he was doing in the building,” Willesen shares. “Those memories can’t be recreated, but they can be preserved for generations.”