To report on contextual variance in the distributed rural family medicine residency programs of 3 Canadian medical schools. A constructivist grounded theory methodology was employed. Rural and remote postgraduate family medicine programs at the University of Alberta, the University of British Columbia, and the University of Calgary. Twenty-six family practice residents were interviewed, providing descriptions of 27 different rural sites and 10 regional sites. Interviews were audiorecorded, transcribed verbatim, and thematically analyzed. Participants differentiated between main campus academic health science centres; regional referral hub sites; and smaller, rural, and more remote community sites. Participants described major differences between sites in terms of patient, practice, educational, physical, institutional, and social factors. The differences between training sites included variations in learning opportunities; physical challenges related to weather, distance, and travel; and the social opportunities offered. There were also differences in how residents perceived their training sites, both in terms of what they noticed and how they interpreted their observations and experiences. Although there were contextual differences between regional sites, those differences were a lot less than between different smaller rural and remote sites. These differences shaped the learning opportunities available to residents and influenced their well-being. Although there may be some similarities between distributed training sites, each training context presents unique challenges and opportunities for the family medicine residents placed there. More attention to the specific affordances of different training contexts is required.