Initially, Miss Jacobi began her program as a "brother-and-sister" school, counting among its first students the son and daughter of Franz Boas, one of the founders of American cultural anthropology.

It gradually evolved into a girls' school, attracting the daughters of socially prominent Jewish families, including Peggy Guggenheim, the children of the Morgenthaus and the Strausses.

Eleanor Steiner Gimbel remembered Miss Jacobi's commitment to civil liberties and her "teaching of race understanding as one of the high points of her school days.

[6] Calhoun offers an extensive physical education program that promotes team play and individual fitness, and a full roster of interscholastic sports under the auspices of the New York City Athletic League (NYCAL).

[8] DesignShare, a journal of educational facilities planning, called the four-floor addition a "courageous design," with special mention of the School's Green Roof as "an innovation in the architecture for learning.

Ten years later, in the summer of 2014, the school began another 3-month renovation project of the 81st Street building with FXFOWLE, to expand the interior of the first floor by enclosing an outdoor plaza.

[9] The result had a significant—and positive—impact on the face of the iconic building while maintaining the "overhang" effect that—when first built in the 1970s—people claimed looked like a Brownie camera flash cube or a television set.

The yearly series hosts professional Children's Theater, Music Concerts, Dance, Documentary Films, and Town Hall Meetings and Lectures, all at nominal cost and all open to the public.

[10] Students and faculty have the added benefit of meeting with many of these artists and guest speakers prior to the events, in class or specially arranged assembly programs.