The fountain in front of the Woodrow Wilson School was created by James Fitzgerald in 1966 and is one of the largest bronze castings in the United States. Fitzgerald named his work the "Fountain of Freedom" to symbolize Woodrow Wilson's vision of lasting world peace.

For some Princeton seniors, however, the fountain represents a different kind of freedom: the completion of their senior theses. Each spring, Woodrow Wilson School seniors continue the tradition of jumping into the fountain after handing in their papers. Also, whenever the Tigers win a home football game, the Princeton University Band plays a celebratory a concert from inside the fountain's pool.