A large amount of research has been conducted on play and in recent years the disappearance of play has been questioned (e.g., Brown in Kindergartners get little time to play. Why does it matter? 2016; Ebbeck and Waniganayake in Play in early childhood education: learning in diverse contexts, Oxford University Press, South Melbourne, 2016). Researchers and practitioners alike have expressed serious concerns that academic pressures on the curriculum have reduced the amount of time given over to play (Nicolopoulou in Hum Dev 53:1-4, 2010). This paper raises some important issues in relation to outdoor play and presents a research study conducted in Singapore--a highly urbanised country. The research examined early childhood teachers' views on the value of outdoor play and their teaching practices in outdoor play with young children. Findings showed that most teachers enjoyed conducting outdoor activities; however, they were concerned about the lack of physical and human resources. At a follow up sharing of the research results, teachers were able to suggest some ideas to cope with the challenges identified in the study findings. Implications are drawn for practitioners, education policymakers, and for town planners working in urbanised countries like Singapore.