It is a member of the Connecticut Association of Independent Schools.

The Wooster School motto is Ex Quoque Potestate, Cuique Pro Necessitate, roughly, "From each according to ability, to each according to need".

Founded in 1926 as a boys' school of 10 students by Episcopal priest Dr. Aaron Coburn,[1] it is named for General David Wooster, who fought at the Battle of Ridgefield with the Patriots in the American Revolution.

[3] The school continues the legacy of the jobs program, in which the entire student body engages in a daily period dedicated to cleaning and physically maintaining the campus.

[5][6] From 2001 to 2004, Wooster School made some improvements to its physical plant, notably the addition of a new gymnasium and a distinct Middle School building.