The Underground was first opened at its current location on April 26, 1974 as "The Cage." It has a history of being operated and funded by students and providing lively entertainment and an atmosphere for fun and socializing. It has undergone many changes since it first opened. It began when live music was popular and moved into a phase of disc jockeys.

During the early 1980's the name was changed to "Ichabod's." Initially, Ichabod's obtained funds through the Student Activities Board. Due to the efforts of the former members of Ichabod's staff and the Ichabod's Administrative Committee (IAC), self-sufficiency was attained for several years, receiving no direct programming funds from SAB. In 1986, however, the College lost the liability coverage which allowed Ichabod's to sell beer.

That, along with legislation raising the drinking age to 21 yrs (with a grandfather clause) and the national trend to promote alcohol-free events, made it necessary for the student pub to "go dry" for a year. When Ichabod's went dry, the Board of Trustees, recognizing the value of Ichabod's to the campus, gave renovation funds to help counteract the effects of its inability to sell alcohol. Effective for the 1987-88 school year, however, Ichabod's again began selling beer to anyone 19 yrs old by July 31, 1987.

After successive years of decreasing attendance more changes seemed necessary. During the spring semester of 1989, the IAC discussed and implemented a majoy plan for renovations funded by college capital funds. The changes included structural changes to the entrance, new tables and chairs, fresh paint, audio equipment cabinets, televisions, a VCR, a microwave, a new cash register, and a new name, The College Underground.

Having celebrated its 35th anniversary in April 2009, The Underground receives some funds for programming, although it is generally a facility in which other campus groups and departments program their events. The Underground shares a close relationship with Wooster Activities Crew (W.A.C.), the student activities board, for they still plan many events in The Underground each semester. Other campus organizations may reserve the facility to host parties, bands, talent shows, etc. The Underground staff is encouraged to generate ideas of events on their own to enhance the atmosphere at The Underground. Over the past few years, the popularity of The Underground has substantially increased, particularly with Dance Parties. The Underground is in a constant state of change and has much room for growth.