Through an integration of philosophical analysis and qualitative fieldwork, this dissertation explores understandings of and approaches to character formation in the context of contemporary K-12 classical education. Although classical education is associated with a range of cultural, curricular, and pedagogical features, I argue that the heart of the approach is distinguished by the foundational philosophical and anthropological commitments of classical education. These commitments support a vision of character education centered on the formation of love and the creation of aspiration. Given this broad framework for character formation, I examine a pair of virtues that I suggest are very important within this perspective: humility and magnanimity. Drawing on philosophical texts and the richness of my fieldwork, I argue that classical educators can be understood as seeking to cultivate humility through engagement with tradition and magnanimity through a holistic elevation of school life. I conclude by addressing some challenges for classical education, ending with a call for classical educators to maintain the integrity of their work by pursuing humility and magnanimity themselves.