The initial transition to graduate school provides a critical opportunity for promoting a positive educational experience among incoming students. This study discusses the importance of this transition and then describes a novel student-led orientation approach to facilitating successful entry of new students into criminology and criminal justice graduate degree programs. Results from an evaluation of this approach are presented. Analyses of focus group and student survey data indicate that graduate students matriculating into a criminology and criminal justice program in a southern state felt welcomed and found the information, guidance, and social networks that they developed to be helpful. At the same time, students identified ways the orientation could be improved for future cohorts. A student-led orientation, along with evaluation of it, provides a promising strategy for criminology and criminal justice graduate programs to create positive educational and professionalization experiences for their students.