Originally known as the Riverdale School for Boys, it began with 12 students and four teachers and promised scholarly, intimate teaching amid abundant recreational space.

In 2018, Riverdale was in the news[11] for cancelling an Israel-Palestine seminar,[12] purportedly forcing out a teacher who had taught at the school for over 25 years, even though parents stated that he welcomed debate.

[13] In a Huffington Post article, titled "How An Elite New York City Prep School Created A Safe Space For Angry Zionists," board members Tal Keinan, Dan Rosen, Seth Berger, and David Westin were reported to have used their status as donors and board members to organize meetings with the Headmaster and pressure him to fire another teacher.

[14] The article notes, "By HuffPost’s calculations, the parents who received the May 30 email had donated upward of $500,000 to Riverdale in the 2016–17 fiscal year alone.

Specifically, an individual or couple is listed as having given anywhere between $10,000 and $24,999, $25,000 to $49,999, over $50,000 and so on — meaning one year’s worth of their donations could easily have surpassed seven figures.

"[14] In 2022, media reported that Richard Blumenthal, a senator from Connecticut, had helped establish Riverdale Country School's “Slave Day” when he was president of the student council in 1962.

[15] Riverdale also attracted attention in 2021, for allegedly teaching students to monitor each other in order to determine if they were practicing "allyship" sufficiently, which meant that those perceived as non-compliant would be reported to school administrators.

[16] The practice, introduced as a replacement for the Pledge of Allegiance, caused Bion Bartning to withdraw his children from the school, protesting "a kind of religion taking hold in American education that forces people into categories according to their race.

[18] Covering 19.5 acres (79,000 m2), the Hill Campus is located on Fieldston Road, overlooking Van Cortlandt Park.

Interdisciplinary courses in the Lower, Middle, and Upper Schools encourage students to draw connections across disciplines.

Integrated Liberal Studies is required of seniors and concentrates on virtue, the self, social justice, and the environment.

[24] Riverdale students may participate in the jazz and concert bands, orchestra, chamber music ensembles, chorus, dance team, and the a cappella singing groups, the Rivertones and Testostertones.