Abby F. Goodsell ’69, who was a teacher in the department of ancient languages from 1872 until 1874 and who became assistant to the lady principal in 1874, was appointed lady principal.

The musical soirée prelude to the commencement events for 1881 was given by graduating students in the School of Music, among them Shigeko Nagai, Gertrude Nichols and Fanny Littlefield.  

Vassar’s Class Day exercises for the Class of 1881 began at 3 pm in the Chapel.  Students and guests watched as the seniors and juniors entered to the music of an orchestra from New York’s Twelfth Regiment Band.  Class president May Bryan ’81 called upon class orator Caroline White ’81, class historian Mary Stockwell ’81 and class prophet Alice Shove ’81.  “The oration, history, and prophecy,” The New York Times reported, “were full of hits and sarcasm, and much applause followed each.”

Marching to the band’s music, the assembly moved to the class tree, where Caroline Augusta Lloyd ’81 bid “Friends and Fellow Students” welcome and said that the tree was planted “to sing the glory of her class in coming years, to whisper ‘”81’ in the idle breeze of Summer, and to shriek it through the naked boughs in the wild storms of Winter.”  After the burial of the class records under the tree and the junior reply by Ella Varns ’82, the class song was sung, to the band’s accompaniment, and the afternoon’s exercises concluded.

During the afternoon, at the annual June board meeting, President Caldwell acknowledged that Vassar was experiencing a significant decline in students and resulting financial difficulties.  He attributed these problems to the establishment of Wellesley, Smith and the Harvard Annex, and he called for an increase of $200,000 in the college’s endowment funds.

In the evening the college grounds were illuminated by calcium lights for an outdoor promenade concert.

President Caldwell conferred the baccalaureate degree—“that mystic ceremony which transforms the chrysalis Senior into the brilliant butterfly, the alumna,”according to the Vassar Miscellany—on 35 members of the Class of 1881. The "Oratio Salutatoria," given by Maria Abbott, was followed by seniors' essays on "Dogmatism in Science," "The Utility of the Study of Philosophy," "The Province of Mathematics in the Curriculum," "The Papacy in the Fifth and the Ninth Century" and "The Emotional Element in Religion." 

The question in the traditional debate, "Is the Negro Doomed?" was argued by Alida Katharine Fitzhugh in the affirmative and, in the negative, by Annie Lowry Lyon. The "short but impressive" validictory address was given by Mary Lora Freeman.

President James A. Garfield was shot in Washington, DC.  He died, exactly two months before his 50th birthday, on September 19.

Matthew Vassar, Jr., nephew of the Founder, died in Poughkeepsie after a brief illness, aged 73.  He and his brother, John Guy Vassar, had retired from the family brewing business in 1863 and had engaged in several philanthropies, including the college's Vassar Brothers Laboratory, in 1879, and a Poughkeepsie home for aged men, in 1880, built on the site of Vassar Jr.’s birthplace, the house erected in 1702 by Poughkeepsie’s founder Baltus Van Kleeck, Vassar Jr.'s mother’s great-grandfather.

Matthew Vassar, Jr., served as the college’s treasurer and the overseer of its endowments until his death. His will contained bequests to the college of nearly $150,000, along with provision for his share of the Vassar Brothers Hospital, completed by his brother, John Guy Vassar, after his death.