According to The College on The Hill a book about the history of SDSU, in 1911 the South Dakota State College administration declared that it was “undignified” for college women to be wondering the streets of Brookings in bed sheets. Effectively ending, what had been since 1907 a yearly homecoming tradition, known as the nightshirt parade, in which male students would dress in their nightshirts and female students would dress in bed sheets and then parade through town before the homecoming football game.

Homecoming in 1912 looked to be in a bit of trouble until Adams Dutcher suggested holding a Hobo Day as a possible substitute for the nightshirt parade. Dutcher had apparently witnessed a similar event at the University of Missouri. Thus on November 2, 1912 the men of South Dakota State College dressed as hobos, the women dressed as Indians and marched down to the Brookings train station to welcome the Yankton football team.

The celebration took hold and for all but two of the last 100 years SDSU has celebrated Hobo Day. There have been many changes throughout the years, the bum mobile arrived in 1939, Weary Wil and Dirty Lil were adopted as the official mascots of the celebration and a number of other traditions have sprung up around the largest one-day event in the Dakotas.