1990
An After School program until 5:30 each day is started. The school begins a Students of Color lunch/affinity group. The school conducts a Multicultural Assessment Plan (M.A.P.).
The new Beginners Building & Lower School Commons is completed.
1991
The concept of a Flex Week in April is approved by faculty as a permanent part of the curriculum.
1992
The Alumni Board hosts a Faculty Festival in May. More than 500 people participate in the celebration honoring teachers who had taught at the school for 20 years or more: Ruth Abbott, Bill Bellows, Faith Chase, Di Droste, Mary Eliot, Madeline Gabron, Marjorie Gatchell, Jane Hakes, Jerry Hakes, Jane Hardy, Bob Lawler, Don Mapel, Ted Martin, Jack McKernan, Oddvar Nordal, Vera Nordal, Jean Seaver, Carol Segar, Joe Segar, David Smith, Adelaide Sproul, Agnes Swift, Susan Walsh, and Ed Yeomans. The event included a panel presentation about "The Challenges of the Times for Shady Hill School," class visits for former faculty and apprentices, alums, and parents, an Artsfest and Songfest, and a gala dinner.
The school becomes a two-division school, rather than a three-division school. Because of declining interest, the school no longer offers Latin as a language option.
1993
The Board of Overseers and faculty participate in anti-racism training. The school creates the position of Diversity Coordinator.
Medieval Civilization becomes the Grade V central subject.
Jonathan Slater announces that he will leave at the end of the 1993-1994 school year.