Using land owned by William Lynn's mother, they constructed a school building and opened enrollment for students in 1972.

William Lynn also wrote the first Word of the Day and Great 100 books and established traditions such as the annual competition between "Spartan" and "Athenian" athletic teams.

[7] Throughout this process, Wakefield Country Day School, at its original campus and under the leadership of founder Pamela Lynn, continued to operate.

Because of low enrollment, it has experienced funding crises that threatened to force its closure, but it has always survived thanks to donations and long-term loans from the alumni and community at large.

Through the 10th grade students spend two class periods per day studying English literature, composition, vocabulary, and grammar.

Ambassador to Uzbekistan Jon Purnell; investigative reporter and editor of the Rushford Report[14] Greg Rushford; attorney, law professor, and Senior Vice President at the Campaign Legal Center Paul M. Smith; and former Clerk of the United States House of Representatives Jeff Trandahl.

They also speak at the WCDS Forum, which is an opportunity for the public to hear adjunct faculty discuss topics and engage one another in expert dialog.

[16] From May to November 2019, benefactors donated more than $2 million to the school for tuition assistance and to support ongoing operations.

[18] From 2020 to 2024 the school received major gifts from two anonymous donors, and one from Tobias Dengel, WCDS 1989, President of WillowTree, and his wife, Lynn.

The school's colors are red and white; in the Spartans vs. Athenians competition, which is inspired by the Ancient Olympic Games and serves essentially as a field day, the students are divided into two teams, with the Spartans wearing red and the Athenians wearing white.

First, each team assembles into a formation of parallel rows for inspection by the faculty for proper discipline and deportment.

[24] While stationed overseas in the Iraq War, he wrote a series of guest columns to the Culpeper Star-Exponent about his experiences and observations as a tank platoon leader.

[25][26] After exiting his tank[27] to secure a building near Karbala's Mukhayam mosque, which had been the scene of intense fighting during a recent raid to oust the Mehdi Army insurgents who had been using the mosque as a base of operations,[28][29] he received enemy sniper and rocket-propelled grenade fire and was killed.

[31] Another notable student was Jacob G. Foster, who placed number one in the world on advanced placement tests in French literature, calculus, modern European history, biology, Latin, physics, and other subjects; scored a perfect 1600 on the Scholastic Aptitude Test;[32] and became a Rhodes scholar and later a mathematical physicist and sociologist.