There has been a decline in children’s use of active school transportation (AST) while there is also limited research concerning AST in winter conditions. This study aimed to explore the prerequisites and experiences of schoolchildren and parents participating in an empowerment- and gamification-inspired intervention to promote students’ AST in winter conditions. Methods: Thirty-five students, who were aged 12–13 years, and 34 parents from the north of Sweden participated in the study. Data were collected using photovoice and open questions in a questionnaire and analyzed using qualitative content analysis. Results: The results show that involvement and togetherness motivated the students to use AST. In addition, during the project, the parents changed to have more positive attitudes towards their children’s use of AST. The students reported that using AST during wintertime is strenuous but rewarding and imparts a sense of pride. Conclusion: Interventions for increasing students’ AST in winter conditions should focus on the motivational aspects for both children and parents. For overcoming parental hesitation with regards to AST during winter, addressing their concerns and empowering the students are key factors. To increase the use of AST all year around, targeting the challenges perceived during the winter is especially beneficial.