Throughout the school's history, students were open to wander the woodlands and gardens, utilize the lawns and tennis courts, and swim in the Olympic-sized pool.

The school had a gymnasium class, amateur theater group, folk singing, a swimming pool, and an economic forum.

The school flourished during almost two decades under the helm of Dr F. Dean McClusky, who went on to a career as a professor in the Department of Education at UCLA.

Frank Vanderlip enjoyed teaching simplified political economy at the school; he would act out Swiss Family Robinson on an imaginary island with students to demonstrate the development of capitalism.

A 1959 development plan made way for a new primary school in 1961, new science facilities in 1962, expansion of the library in 1963, and the creation of an organization for alumni, of whom there were more than a thousand living in 1977.

In 1980, the buildings and property were taken over by The Clear View School Day Treatment Center, which opened in September 1981 after major renovations.

[11] The main Scarborough School building, Vanderlip Hall, was designed by William W. Bosworth, known for landscaping Kykuit and restoring Versailles.

[8] In addition to a grand porticoed entry, there were two wings that housed classes, a library, cafeteria and gymnasium, basement science labs, and an art room measuring 1,000 square feet (93 m2), ringed on three sides with French windows.

[5] Details were closely examined upon construction; the lighting equipment, the scene lofts and fly gallery, and the dressing rooms were well-designed and state-of-the-art.

Lecturers and performers in the Beechwood Theater included Sarah Bernhardt, Robert Frost, John Masefield, Vachel Lindsay, Eleanor Roosevelt, H. G. Wells, Stephen Vincent Benét, and a King of Siam.

Frank Vanderlip Jr., ten years old at the time, later recalled that he saw the detonation shake the jammed theater building, and that Paderewski had played on as if nothing had happened.

The automatic fire doors at the top of the theater had sprung open, and two men were sent aloft to sit on them until the end of the performance to prevent a cold draft from entering the room.

[4]: 109  Other notable alumni include Mark Helprin, a writer who graduated in 1965;[17] the three children of Ely Jacques Kahn, Jr.;[4]: 218  John Kelvin Koelsch, a U.S. Navy officer during the Korean War and the first helicopter pilot to receive the Medal of Honor, who also lived in Scarborough;[18] Ralph J. Menconi, a medallic sculptor; Ilyasah Shabazz, an author and a daughter of Malcolm X; and Richard Yates, a writer who attended from 1937 to 1939 while his mother taught sculpture there.

[19] The theatrical traditions of the school attracted many pupils with interests or family connections in the performing arts, including actresses Joan Evans, Tina Louise, Alexandra Berlin,[20] Broadway producer Dasha Amsterdam Epstein,[21] musical theater composer Henry Krieger[22] (who attended the school with his sister), Margot Feiner (a niece of Richard Rodgers), and Daniel and Margaret Da Silva (children of Howard Da Silva[23]).