Discussion on toddlers’ outdoor play practices in various cultural spaces is rare in literature. In Australia, toddlers’ physical development and well-being is promoted but less attention is given to cultural nuances of outdoor play. We ask the question: How does outdoor play impact on toddlers’ imagination and cultural formation? Conducted in three Australian long day care (LDC) sites, an ethically approved project “Studying babies and toddlers: Cultural worlds and transitory relationships” examines the process of three Australian toddlers’ outdoor enculturation. The concepts of imagination and play from Vygotsky’s cultural-historical theory are drawn upon in relation to Hedegaard’s institutional practices model, to link contextual relations between society, community and family. Cultural formation processes in toddlers’ outdoor play, we argue, are more completely understood when daily life across home and local community is acknowledged. Data findings illustrate complexity of movement and experimentations in cultural conditions, where different spaces hold possibilities for imaginative transformations in toddler’s play. Implications suggest toddlers’ imaginative and culturally responsive outdoor play aligns with availability of interested adult/peers, shared family and community values, and varied local spaces. In this way, affective and dynamic outdoor interactions imbue cultural formation of toddler’s play and imagination with local personal meaning.