Shady Side Academy was founded in a one-room schoolhouse in the Shadyside section of Pittsburgh in 1883. Since its founding, Shady Side Academy has seen many changes, including the addition of a Junior School in 1909, the move of the Senior School from the city to a "country" locale (Fox Chapel) in 1922, a merger with The Arnold School in 1940, the opening of the first standalone Middle School in Western Pennsylvania in 1958, coeducation in 1973, and a 2017 merger with Fox Chapel Country Day School, which gave the Academy a second elementary school campus, Country Day School.
Today, Shady Side Academy enrolls more than 1,100 students across four beautiful campuses, offering a unique and balanced education of academics, arts and athletics and a diverse and inclusive learning community. Nearly 100 percent of SSA graduates go on to further their education at a four-year college or university. The Academy boasts an extensive global network of alumni who remain an important part of the Shady Side community.
The Academy celebrated its quasquicentennial (125th) anniversary in 2008-2009.
- Members of the Shadyside Presbyterian Church found a college preparatory academy for their sons, called “Shady Side Academy" and located in the Shadyside neighborhood of Pittsburgh's East End.
- Initial grades for the school were 7-12, known as “Forms I-VI.”
- William Ralston Crabbe becomes the first “principal” of Shady Side Academy
- Shady Side Academy and three other schools form the Western Pennsylvania Interscholastic Athletic League (WPIAL); Principal Crabbe serves as the WPIAL’s first president.
- A Junior School division is added to the Academy (grades K-6).
- Principal Luther Adams invites the Country Day Association of America to meet in Pittsburgh, hosted by Shady Side Academy.
- U.S. entry into World War I, as well as the emergence of public high schools such as Peabody and Schenley, results in a considerable drop in enrollment, and the Academy almost closes its doors forever.
- Under new “headmaster” Harold Nomer, Shady Side Academy begins its first substantial capital campaign and starts to plan for its “country school” campus in suburban Fox Chapel.
- Ground is broken at 423 Fox Chapel Road in February; builders lay cornerstone of Rowe Hall in May; and new “country school” campus opens in October with only two buildings (Rowe and Ellsworth) near completion.
- Senior School (grades 8-12) moves to new Fox Chapel campus; Junior School (grades K-7) stays in Shadyside.
- Shady Side Academy merges with The Arnold School for Boys; Arnold’s seven-acre campus on South Braddock Avenue in the Point Breeze neighborhood of Pittsburgh's East End becomes the Academy’s new Junior School campus.
- Original property in Shadyside is sold to the University of Pittsburgh (and later to Winchester Thurston School).
- Shady Side Academy opens the first standalone Middle School in Western Pennsylvania, serving grades 6-8 and housed in a mansion on a 30-acre property just north of the Senior School in Fox Chapel.
- Shady Side Academy experiments with coeducation, as no local schools are available in Fox Chapel for girls in grades 6-8. Forty-four girls, including faculty children, attend the Middle School in the late 50s and early 60s.
- African-American students are admitted to the Middle School (later to the Junior School in 1964 and the Senior School in 1966).
- After briefly considering a merger with The Ellis School for Girls, Shady Side Academy’s Senior School adopts coeducation and the first girls are admitted to grades 9-12. It would be nearly 25 years before coeducation is formally adopted at all three divisions (Junior School in 1994; Middle School in 1997).
- The first K-12 female “Lifers” graduate from Shady Side Academy.
- Shady Side Academy opens a pre-kindergarten program in a new free-standing facility on the Junior School campus;
- Shady Side Academy merges with the PK-5 independent school Fox Chapel Country Day School, which becomes the Academy’s second elementary (PK-5) campus, Shady Side Academy Country Day School in Fox Chapel.