In my timeline, I present the evolution of college from its foundation at the University of Bologna in the eleventh century to contemporary initiatives centered on the idea of a more accessible and affordable academic institution. In particular, I focus on the triumphs that college as an institution reached in the course of time, as well as on the struggles and frustration inherent to this academic path. For instance, to cite one of the positive entries, the formulation of the Constitutio Habita, an historical document in which for first time rules, rights, and privileges of universities are officially defined, is a moment of great importance in history as today’s generations are still enjoying the results of this conquest in terms of academic freedom. In contrast, to cite an example from the negative entries, poor nutrition is a major problem today on the university campuses of the United States, as many students cannot follow a healthy diet due to the sudden transition to a new lifestyle, irregular schedules, lack of sleep, and bad eating habits. While motives of pride were more common in the past ages, nowadays college tends to be associated with social and cultural issues. As we can see, college has its ups and downs as many other institutions. However, it seems that there is space for improvement as some people have recently worked on interesting initiatives that aim to promote a more positive image of college. For instance, Shai Reshef founded an online institution that spreads awareness of higher education’s importance, and at the same time widens the range of students who can afford a degree. Therefore, the timeline emphasizes the role of college throughout history by underlining its negative and positive consequences on the student population and even those who cannot afford to be students in modern society.