While the classical education program finds its genesis with the pagan Greeks, Christendom has long seen the value in a program that has as its goal the freedom of human beings. We can see from the Medieval period that the classical program is best worked out when it is appropriated within a rich and robust Christian worldview which values Truth and sees the human being as a glorious image bearer of God. At the same time, the goal of the classical, liberal arts tradition has always been to produce men and women who seek out Truth by questioning, investigating, and dialogue. This can only be done when there are questions to ask and matters to be discussed. Thus, a theological foundation that is too thorough might stifle a true search for knowledge by rendering all of the important questions answered. The quest for knowledge and understanding, according to Socrates, begins with acknowledging one’s own ignorance. We can also find wisdom in this approach by understanding how the modern search for certainty had the ironic effect of ushering in our relativistic age of uncertainty. Therefore, it seems appropriate both historically and philosophically to root the classical, liberal arts tradition in a creedal Christianity which provides a proper trajectory for the educational program, places limits on the paths which it can take, and allows freedom for those paths to be explored in an intellectually honest manner.