It was founded in Huntly, Virginia in 1972 as Wakefield Country Day School, and changed its name to Wakefield School in the early 1980s when it established a small boarding department (boarding was discontinued after a few years).

After a disagreement with the founders of the school, half of the board of trustees moved the school from the Huntly location and re-founded the school at Marshall, Virginia in 1991, and moved later to Archwood Farm in The Plains (the first campus owned by the board of trustees) in 1996.

Between 1996 and today, Wakefield grew from a school of 240 students to the current enrollment of about 332 as the campus was developed.

Significant alums include reddit and Hipmunk cofounder Steven Huffman.

Wakefield is a member of the Greater Piedmont Athletic Conference (GPAC).