Colorado Springs' first classical Catholic high school opened in 2021 as Chesterton Academy of Our Lady of Walsingham, one school in a network of 50 private Catholic high schools in the U.S. and Canada. The school re-launched fall 2023 as Our Lady of Walsingham Academy.

"The resources and services of the Chesterton Network are designed primarily to assist those new to, or unfamiliar with, the operation of a classical Catholic high school," said headmaster Mark Langley.. "Since the school was founded, we've been able to attract to the faculty some real veterans of classical Catholic education, folks who bring a world of experience to our enterprise. Add to that the preference for local autonomy based on the Catholic concept of subsidiarity and it became clear that the independent route was the best way for us to deliver an education true to the classical Catholic tradition."

Our Lady of Walsingham is a title for the Blessed Mother first popular in 11^th Century Europe.  The logo renders the school's name in an Old English font reminiscent of calligraphy-crafted medieval manuscripts. The seal is flanked by the treble clef, a nod to the sacred music and student choir for which the school is known, and finished by the Greek letters Alpha and Omega as Jesus Christ calls himself in the book of Revelation. The Madonna is depicted with a Saxon crown to reference Walsingham, England, and holds a royal scepter of three lilies to denote the Holy Trinity.  The Christ Child extends a two-fingered blessing to reference the dual nature of Jesus and holds a book to represent both the Gospels and the Great Books of Western Civilization upon which the school curriculum is based. A shield version of the logo also includes a chalice to reference the importance of the sacraments in religious formation, and is segmented by a "budded cross" wherein the 12 buds that cap the cross allude to the apostolic Catholic Church.