Student affairs is a relatively new profession in higher education, and only recently has its history begun to be systematically examined. This article describes one of the earliest venues in which student affairs leaders gathered to discuss current issues and to reflect with colleagues about the emerging student affairs profession. This article identifies the changing topics discussed at Allerton House in Monticello, Illinois, over a period of 45 years, as well as the special legacy that the Midwest Deans meeting had for many student affairs staff throughout the Midwest and nation. Although this article examines the conference only through 1993, the year the author stepped down, others have managed the conference, which continues to occur annually.