This chapter considers challenges in researching outdoor play and learning that involves children and young people actively moving through space and time. It illustrates some of these through case studies drawn from the authors’ empirical research, reflecting that resolution of some problems through participative and dynamic methodologies may yet produce other issues such as distortion of the focus of study or privileging anthropocentric perspectives. A common strand across the described methods is acknowledgement that reliance on words alone will not enable the researcher to understand the multisensory context of outdoor studies, and that multiple data sources help us to appreciate its complexity.