Shady Side Academy is an independent preparatory school Fox Chapel, Pennsylvania in Greater Pittsburgh.

[7] Formed to provide for the education of the sons of newly moneyed industrialists of Pittsburgh's East End,[8] the academy counts the Frick and Mellon families among its early patrons.

The school is a member of the Chewonki Foundation's Maine Coast Semester at Chewonki in Wiscasset, Maine, CITYterm at the Masters' School, and the High Mountain Institute's HMI Semester in Leadville, Colorado, and sends a significant number of students to both programs annually.

[15] Shady Side Academy was founded as an all-male day school in 1883, on Aiken Avenue in the East End neighborhood of Shadyside, Pittsburgh.

The $6.8 million renovation of this primary Senior School facility emphasized environmentally friendly approaches, from glass that allows more light into classrooms (allowing the building to maintain lower electricity usage levels) to rainwater collected in an underground cistern, then used to flush toilets and urinals.

In the fall of 2007, the Rowe Hall Complex earned Gold LEED (Leadership in Energy and Environmental Design) Certification, becoming the only high school in the Commonwealth of Pennsylvania to have done so.

The Mcllroy Center is a Gold LEED-certified "green" building with sustainable features that reduce environmental impact while creating teaching opportunities, such as a rooftop solar array and monitoring system and a rain garden to collect storm runoff.

[17] Academic life at Shady Side Academy operates on a trimester system, dividing the year into three thirteen to fourteen-week terms.

Classes begin each year before Labor Day with Convocation in late August and finish with Commencement exercises in early June.

Because students spend weekends at home, boarders almost always came from the three-state area of eastern Ohio, western Pennsylvania, and northern West Virginia.

The academy also houses residential faculty representing almost every academic department, both in apartments in the dormitories and homes on the Senior and Middle School campuses.

[25] Since 2003, Shady Side has sponsored a benefit concert called "Untucked"—an homage to the school dress code, which, before 2004, required all shirts to be tucked in.

Untucked is usually held at the end of the year in the Roy McKnight Hockey Center and includes food and carnival games.

The academy's early athletic program was organized to promote the ideals of its day, particularly amateurism in sport and the spirit of Muscular Christianity.

Team sports, initially informal organizations of students and occasionally faculty, became increasingly structured as the academy developed athletic links and interscholastic competitions with nearby public and private secondary schools and, occasionally, colleges such as Washington & Jefferson College and what is now Duquesne University.

After seventy years of competition for the annual "Championship Cup," Shady Side Academy withdrew from the "crumbling" IPSL in 1993.

Although most teams now compete at the varsity level in the WPIAL and PIAA, a minority of programs maintain prep-level affiliations in smaller sport-specific Prep Leagues consisting of other regional independent schools.

It also occasionally plays semi-professional hockey clubs in Germany and Italy, including ESV Kaufbeuren, SV Kaltern, and EV Landsberg.

Shady Side Academy has four campuses in Pittsburgh with almost 200 acres (81 ha), predominantly in heavily wooded Fox Chapel.