Author Alexis Brooke Redding is an advanced doctoral student and instructor in education at Harvard University. In the spring of 2015 she spent six weeks interviewing administrators and students about the myriad pathways that bring students to Hampshire College. More than simply understanding the nature of this singular campus, her study focused on understanding how high school students discover schools that are the best fit for their needs. Highlighting the pathway to a nontraditional institution such as Hampshire College allowed Redding to look closely at how students gain access to information about colleges that are not part of the mainstream dialogue. Over dozens of hours of interviews, students described their pathways to Hampshire. In this portrait, Redding reveals three stories of students who were unlikely to find their way to this campus: a student on a powerful pre professional track to the local university in Colorado; a struggling first-generation student from a college preparatory high school in Texas; and an international applicant from China who had been tracked into a science program as a child. All of these students shared the story of a serendipitous discovery of Hampshire and the process of figuring out that it was a match for their intellectual goals. From engaging in this process, Redding learns that it takes listening to individual stories, again and again, to begin to piece together a picture of where the important gaps exist and, ideally, to consider how one can start to fill them with adequate support mechanisms.