The school was founded in 1889 by Captain Robert Stringfellow Walker, who had been a member of the 43rd Battalion Virginia Cavalry (Mosby's Rangers) during the American Civil War.

Today, the campus is known for its historic Jeffersonian brick buildings and state-of-the-art science and arts facilities.

According to Elizabeth Copeland Norfleet in A Venture in Faith, his plans to go on to law school were interrupted by his father's request that he serve as "head teacher."

Woodberry, nicknamed the Tigers, competes in the Virginia Prep League in a variety of sports, including basketball, soccer, baseball, golf, swimming, lacrosse, wrestling, Cross country running, Tennis, track and field, and football.

Before every game between the two schools, Woodberry has a bonfire reaching heights of four stories, where students line up to throw torches into a tower of logs.

The Tigers send numerous athletes to play college sports at all levels, including multiple NCAA Division I recruits each year.

Faculty undertake a similar process, and later, the administration interviews the individual candidates as determined by the initial elections.