The preparation of medical students for clerkship has been criticized, in terms of both students understanding of their new role as clinical trainees and their ability to carry out that role. To begin to address this gap, the authors report the development, implementation, and assessment of a novel program in which first-year medical students shadow first-year residents during their clinical duties. The program matches each student to a single resident, whom they shadow for several hours, once per month, for eight months. In the programs inaugural year (2009–10), 83 student–resident pairs participated; over 70% responded to pre- and post-intervention questionnaires, which included an 18-item preparedness scale. The authors used those responses to evaluate the program. Compared to students in a control group, the students in the program assessed themselves as better prepared to learn in a clinical setting. The low-cost student–resident shadowing program described in this article provided an early and structured introduction to the clinical environment, which may help prepare students for the transition into clerkship.