Alumni Day was first observed on Lincoln's birthday in 1915. Designed to give alumni a glimpse of campus life when the University was in session (and not just at Commencement or Reunions), the event drew 100 people in what the "Princeton Alumni Weekly" called "an intellectual pilgrimage" to Princeton. From 1916 to 1955, Alumni Day took place on Washington's birthday; thereafter, it was and remains observed on the Saturday nearest to Feb. 22.

Today, Alumni Day draws over 1,000 alumni, parents, friends and family, who attend lectures by distinguished faculty and alumni, family programming, workshops and campus tours. At the Alumni Day luncheon, several awards are presented to alumni in recognition of their achievements and volunteer service. Among those awards are the Woodrow Wilson Award and the Madison Medal. The Woodrow Wilson Award was established in 1956 and is conferred upon an alumnus or alumna of the undergraduate college whose achievements exemplify Woodrow Wilson's memorable phrase "Princeton in the nation's service." The Madison Medal, named for James Madison, the person considered to be Princeton's first graduate student, was established in 1973 by the Association of Princeton Graduate Alumni (APGA). It is conferred each year on an alumnus or alumna of the Graduate School who has had a distinguished career, advanced the cause of graduate education or achieved a record of outstanding public service.

Later in the afternoon, in a tradition that began in 1970, the Service of Remembrance in the University Chapel honors those Princetonians — alumni, students, faculty and staff — whose deaths were recorded during the prior calendar year.