Play Day Origins - Mount Holyoke Senior rope skipping and Junior top spinning, from which Upperclass Play Day evolved, had their origins as part of the activities for May Day, begun in 1896. By 1903, the custom had evolved into two days, one for each of the upper classes. On the first day, the Seniors, dressed in white dresses and cap and gown solemnly processed to the large walnut tree in front of Williston hall, and “for the edification of all, skipped rope.” On the second day, the Juniors, wearing their class color and led by the president and vice president of their class, would process from inside Williston to in front of the library, where they would spin their tops and sing their “spinning song”. The spinning song was often composed by a member of the class and set to a popular tune. Afterwards, the students would keep their tops and jump ropes as treasured tokens of Mount Holyoke. Underclasswomen were excluded from this event since 1899, but in 1917 the freshman class attempted to "trespass upon this sacred rite" by "bringing out hoops, marbles, or balloons", and repeated the attempt their sophomore year.

Upperclass Play Day - By the twenties, the two days of class activities had evolved to one Upperclass Play Day. Both classes participated in “playtime” activities, and for several years nursery-rhyme characters visited the activities, including the Old Woman in the Shoe, and Jack and Jill. For at least one year, participants dressed up as babies and their nursemaids, probably in keeping with the “playtime” feel of the day. Play Day seems to have ceased completely by the thirties, perhaps becoming re-absorbed into May Day celebrations or ceasing altogether with the onset of the depression.