Abstract: The purpose of this thesis was to explore the perspectives of sport parents to understand factors, in particular messages that impact parents and their decisions within the context of children’s sport and free play. Guided by interpretive description (ID), data were collected through interviews with 12 parents who had children between the ages of 8 to 10 years old, registered in a club soccer program. A socioecological framework applied to this study highlighted a multitude of factors, from various levels of influence that impacted parents’ perspectives and decisions within the contexts of children’s sport and free play. In the first manuscript, interviews revealed that parents’ perspectives on children’s sport and free play were influenced by their own personal childhood experiences and framed within the notion that times have changed. Parents viewed competitive team sport participation as a priority over free play, particularly for the development of life skills, socialization, and a sense of community. Free play was primarily viewed for the benefits of relaxation and down time, yet was also associated with increased opportunities for problem behaviours. Schools were seen to play an important role in the sport and free play opportunities and experiences of children. Broader levels of influence in social and physical environments (i.e., sport organizations, coaches, local parenting norms, parenting ideologies) impacted the decisions and behaviours of parents within the context of sport and free play, particularly the accelerated pace of children’s sports, and safety concerns in free play. Parents generally embraced the busier lives that are prevalent in our current milieu. Furthermore, parents generally viewed the multitude of opportunities for children to be involved in, positively. The findings of this study highlighted a gap in the literature with regard to free play in middle childhood, and parents’ understanding of the benefits of it. Furthermore, this study points to the need to consider addressing broader levels of influence, such as physical and social environments in supporting healthful and positive behaviours in the context of children’s sport, free play, and IAM. In exploring the impact of messages in the second manuscript, interviews suggested that formal messages (i.e., mass media commercials, social media, etc.) had limited direct impact on parents’ decisions within children’s sport and free play except to validate decisions already made. Parenting ideologies, local parenting norms, and parenting labels inherent in children’s sport and free play (i.e., helicopter parent, hockey parent, etc.) did influence parent behaviours and decisions. Parents wanted to be the ‘good parents’ rather than ‘that’ parent which are often highlighted in popular media and empirical studies. These parents observed, and opposed the strong presence of the 10,000 hours of deliberate practice theory (Ericsson, Krampe, & Tesch-Römer, 1993) influencing children’s sports experiences, and felt that it challenged their decisions to have multisport children. Furthermore, parents expressed how messages and the information they received were often contradictory. The findings of this study acknowledge that parents recognized the importance of sport and free play yet suggest a tension exists between them highlighting the notion that play is often presented in opposition to sport.