Translation has long served as the vital bridge connecting modern readers to the intellectual, aesthetic, and philosophical worlds of classical literature. From Homer’s Iliad and Odyssey to Kalidasa’s Shakuntala and Confucius’ Analects, classical texts embody the foundational expressions of human thought and creativity. Yet their continued relevance across centuries owes much to the art of translation, which enables these works to transcend linguistic, temporal, and cultural boundaries. This research paper explores the intricate relationship between translation and classical literature by examining how translation functions as a medium of preservation, interpretation, and reinvention. It analyzes theoretical perspectives on translating classics, historical developments from antiquity to the digital age, and the translator’s role as both mediator and creative participant. It further discusses challenges such as linguistic equivalence, stylistic fidelity, cultural transference, and ideological bias, drawing examples from Greek, Latin, Sanskrit, and Chinese classics. Ultimately, the paper argues that translation not only safeguards the legacy of classical literature but also continuously renews its vitality, ensuring that ancient voices remain audible and meaningful in contemporary times.