At the core of Wakefield's methodology in the cultivation of capable, ethical, and articulate citizens is its rigorous academic program.

While the school acknowledges the essential role of meaningful co-curricular pursuits and student leadership outside of the classroom, it is in Wakefield's vibrant classrooms that students are invited to do the kind of disciplined, thoughtful, creative, and inquisitive intellectual work that will complete a core part of the school's mission: to "help students distinguish that which is true from that which is not, and to use that knowledge in positive ways."

Throughout all three Divisions, students are encouraged to master content, to develop sound study habits, and to think independently about what they are learning. The curriculum is characterized by inquiry-based science classes, an English Department that focuses from first grade through twelfth on sound writing and communication skills, and a strong emphasis on interdisciplinary connections.

The confidence that comes with Wakefield's combination of focused scholarship and freedom of speculation shows itself clearly in the Senior Thesis project, a year-long inquiry process into an area about which each student is passionate. While the culminating projects that cap this year of investigation vary widely in form, all reveal that they were created by students not afraid to ask hard questions, and possessing both the skills to seek answers, and the discernment to probe the meaning of what they discover.