The Middle School academic program is centered on a traditional curriculum and is designed to strengthen core skills while preparing the boys for future success in the Upper School. Middle School boys take courses in Art, English, Foreign Languages, History, Mathematics, Music, and Science. Complementing the core curriculum at various points in the Middle School years are courses in Technology, World Religions, Drama, Health, and Character Development.

In the fifth and sixth grade, the boys continue to build upon many skills introduced in the Lower School. The content is not only delivered to increase the boys' understanding of a particular field, but also to learn and develop the fundamental skills needed to be a successful student. Reading, writing, organization, note-taking, and test preparation are just a few of the skills focused on by the boys in fifth and sixth grade. In the seventh and eighth grade, the boys are encouraged to apply these skills to a more intensive, content driven course of study. The students are aided in and out of the classroom by a skilled and caring faculty who help prepare the boys for the transition to Upper School and who understand the challenges of being a Middle School boy.