This paper details the potential contribution of outdoor education (OE) in Singaporean education given the recent raft of national curricular reforms aimed at fostering holistic and exploratory learning opportunities. In this context, we contend that increasing recognition of the value of OE, both internationally and locally, heralds specific challenges within unique Singaporean educational conditions that must be taken into account for this subject area to flourish. In particular, we seek to distil the ways in which local community, cultural and school conditions signal the need for a more place-based and contextualised version of OE. Our analysis further addresses the need for adequate professional development frameworks to be installed in order to enhance existing local teachers' capacities to substantially educate pupils through the outdoors, within a Southeast Asian urban context.