The study of literature begins in the early grades and includes readings from great works of poetry, fiction, and drama. In addition, each student, beginning in grade 1, is required to read during the summer and to report on at least four books chosen to complement their literature course during the upcoming academic year. In eighth grade, students delight in concentrated study of the ideas, drama, poetry, and myths of ancient Greece and Rome. This is followed in ninth grade by a study of general literature and an introduction to philosophical thought. In the tenth grade, the students study American Literature and in eleventh grade, British Literature. Finally, an extensive survey of world literature is conducted in twelfth grade.

In the upper school, students spend about an hour each day reading and discussing the great literature of the western world. A rigorous study of grammar is combined with intense concentration on vocabulary, which includes a thorough knowledge of etymology.

Wakefield Country Day School offers a coherent composition curriculum in the upper school to further improve each student's writing skills. All Wakefield Country Day School prep school students participate in several challenging writing projects. Each year, Wakefield Country Day School students garner numerous awards in regional writing competitions such as the Samuel's Library Christmas Contest and the Virginia Junior Classical League contests. The composition curriculum culminates in their senior year with a required 20-page thesis on topics of their choosing.

Finally, the drama program is a dynamic supplement to literary studies. All 8th grade students participate in a classical drama recital, featuring scenes from Greek tragedies and comedies. The drama class regularly stages Shakespeare and recently performed a delightfully successful adaptation of the Canterbury Tales.

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