Wenona celebrates 140 years in 2026. Since its founding, Wenonians have been driven by the School's motto Ut Prosim, that I may serve. This page traces that journey.

Miss Edith Hooke founded Woodstock in 1886 in a two-storey stone building on the present-day Pacific Highway, educating young girls and boys. She adopted a crest based on the Southern Cross, five white stars in a blue cross with the Union Jack in the upper left quadrant. 'Ut Prosim' sat across the top of the shield; the School name across a banner at the bottom. Both Woodstock and Wenona share this crest, differing only in the name.

The Hooke family ran Woodstock from domestic buildings across North Sydney, moving from the highway to Miller and McLaren Streets in 1890, and then to West Street in 1901. Miss Hooke and her sisters taught a wide range of subjects as the School grew. In 1913, facing ailing health and shifts in education, Miss Hooke closed Woodstock, farewelling its 120 total students and graduates before Easter. She reopened in West Street as Wenona, later moving to St Thomas's, where the School outgrew first a small stone building and then the church hall. Miss Hooke stepped down, and two former Woodstock students, Miss Messiter, followed by Miss Ralston, took the helm. The Ralston family purchased today's School House on Walker Street, where Wenona has stood for the past century.