This Men's Halls Association (MHA) proclaimed an annual spring formal in honor of the Duke of Windsor in 1936, resulting in the first Dormsylvania celebration. When the duke abdicated the English throne to marry a commoner, Wallis Simpson, the men of the dormitories that comprised the MHA were impressed with his decision to choose love over monarchy, and they created a new kingdom, Dormsylvania, for the duke and his bride. The duke was invited to rule over Dormsylvania, but when he declined the invitation, the MHA held elections to choose a substitute duke.

Campaigning for the title of Dorm Duke was fierce. For 10 days, student candidates and their followers had parades, performed skits and stunts, and competed in athletic contests in an attempt to win votes. The week of rowdy competition culminated in the crowning of the Dorm Duke at a semiformal dance.

In addition to the election of the duke, Dormsylvania featured contests for each house of the MHA. The contests included a talent (non-talent) show, beer bash and midnight movie, a bicycle race, an egg throwing contest, a gunnysack race, a beard growing contest, tug of war, a beer chugging contest, a picnic dinner and a bed race. In the late 1960s, the ecology be-in trash pick-up was also added to the list of events. There was a traveling trophy presented to the winner of the title of Dorm Duke, and a Dormsylvania sweepstakes trophy awarded to the house that had earned the most points for contests throughout the week.
From its inception, Dormsylvania became an annual event for the lakeshore dorms and was celebrated for nearly 40 years. The week of festivities was a time for students to forget about the stresses of UW, let loose and celebrate the end of the semester and the coming of spring. The annual event received a lot of attention on campus, and was even featured in a Life magazine article in 1953.

Unfortunately, the magical world of Dormsylvania vanished in the mid-1970s. But, residents of lakeshore dorms still have something to celebrate each spring: The annual spring festival is now called Springfest, and although the traveling trophies, stunts and parades have ceased, Springfest is a collaborative effort among all the lakeshore dorms, and still provides residents with a chance to take a break from classes and celebrate the coming of spring by delivering free movies, music, a housefellow dunk-tank, T-shirt tie-dyeing, picnics and contests.

In addition to Springfest, the Wisconsin Alumni Student Board (WASB) also celebrates the end of the semester when they host the All-Campus Party, sponsoring a week's worth of alcohol-free entertainment and activities for students, faculty, staff and the surrounding community.