This chapter discusses fieldwork as a transition pedagogy. It builds on my experience of a module, ‘Changing Landscapes of Singapore’, one of the pillars of general education that students must fulfil before graduation. Through fieldwork students are immersed in an experiential learning environment where they interact first-hand with the landscapes of Singapore they learn about in the module. The purposes of this chapter are two-fold: first, to share strategies for how fieldwork may be deployed as transition pedagogy to promote a spirit of discovery, networking and peer learning, as well as acquire soft skills that students can take with them as they progress to higher level modules and beyond the university; second, to compare the outcomes of different fieldwork exercises students have had to engage with over the years. In particular I compare lecturer-guided ‘look and see’ fieldwork and self-guided field work using student feedback for the module. The chapter concludes with a summary of the key findings and challenges as well as suggestions for areas of further research.