While classical schools today typically exhibit a carefully considered approach to the linguistic arts of the trivium, the equally important mathematical arts of the quadrivium have received relatively little consideration. This being so, mathematics is often approached in ways that are not distinctly classical. This article seeks to establish the importance of the quadrivial arts as a means of ascending from lower to higher things. Though most know Plato’s comparison of a lack of education to being imprisoned in a cave, (...) relatively few are familiar with the role the quadrivial arts play in ascending from the cave. Because the mathematical arts cultivate and direct the imagination, they enable students to move beyond sensible particulars to the formation of forms and figures by the mind. Thus, the mathematical arts help free us from an undue preoccupation with lower things and direct us toward the pursuit of knowledge and what truly is. (shrink)