Walking is a popular leisure activity throughout much of the world, and is widely endorsed for its benefits to health. Contemporary bushwalking in Australia and New Zealand, while sharing the romantic origins of British, European and American leisure walking cultures (Edensor, 2000; Solnit, 2000), has evolved within the distinctive settings, history and symbolism of the region (Harper, 2007). In recent decades the development of hut-based and designated trails, the availability of lightweight camping equipment, and the growth of support services have encouraged participation in multi-day walking by novices and active older adults. Given the frequent association of long-distance walking with contemplation, self-development and achievement (Edensor, 2000; Pearce, 2011), a closer examination of the walking experience and its outcomes has the potential to offer insights into the under-researched transformative potential of travel, and associated benefits to well-being through positive personal change. This chapter presents and discusses findings of a study exploring ways in which adults come to make positive changes in their lives following longdistance walks. Guided and self-guided walking experiences are included in the study, in settings recognised for their natural or cultural significance. The research presented here is part of a broader qualitative exploration of transformative experiences associated with long-distance walks within Australia and nearby regions. Participants, recruited through walking clubs, websites of popular tracks and snowball sampling, were self-selected after having ‘personally significant’ experiences on a walk of at least three days duration. In-depth, semi-structured interviews (Wengraf, 2001) were carried out with 25 adults, including follow-up interviews with participants who reported significant change. Additional insights were obtained from personal journals and other written material provided by participants. A phenomenological approach is taken in the analysis, with themes and interpretations emerging from participants’ articulation of their walking experiences, reflections and subsequent actions. The nature of any self-reported change is explored, along with insights participants provided about their change processes.