This article examines two Canadian high school work experience programs that focus on rural youth. The first encourages students to consider work in skilled trades, while the second encourages them to become qualified as healthcare aides. Both programs were designed to encourage high school students to explore careers in fields where labor market shortages were anticipated. Yet as this study shows, they are likely to perpetuate gender-based inequalities in the economic and social mobility of rural youth. We draw on socio-cultural learning theories to show how socialization and workplace practices serve to reinforce gendered participation patterns in healthcare and trades. We conclude with the recommendation that policy related to youth career exploration and work experience include strategies to disrupt social processes that systematically disadvantage rural women.