The interpretation of landscape, the significance of walking and the relationships that exist between them are rarely considered or critically examined in much of leisure research or outdoor pedagogic practice, despite their significance within other fields of academic study such as anthropology and cultural geography. This research seeks to explore how a variety of landscapes are perceived, how cultural and social interpretations influence this perception, and whether these interpretations may be re-envisioned by walking, or wayfaring, as an alternate way of making understandings and meanings with landscape. In exploring the disparate interpretations surrounding landscape, the concept of place and its specificity comes to the fore, as does the importance of the relationship between walking and how we make sense of place. A mixed methodological approach is employed to explore this relationship, combining auto-ethnography, phenomenology and the practice of walking itself. Utilising written notes, photographs, and recordings of personal observations and impressions made whilst on a combination of single and multi-day walks in a variety of locales both familiar and unknown in England, a series of reflective narratives were produced. These narratives serve to describe the experiences gained whilst wayfaring, and provide the data through which critical consideration is given regarding how landscape and place are interpreted in cultural and social contexts. Themes emergent from the narratives and discussed include psychogeography and the urban environment, countryside and suburbanisation, and landscape as amenity. In addition, consideration is given to stories of place, authenticity of place, the changing demographics of walkers, walking alone and with others, walking in different types of landscape, and the significance of paths. Key findings are that landscape is increasingly becoming places of consumption through practices of conservation, urbanisation, heritage and recreational amenity that produce a homogenous and hybridised character, and reflects an urban sensibility in regards to rural culture and nature. This might be resisted by walking where an engagement with the sedimented characteristics of a taskscape and its multi-generational footpaths are experienced. Such an embodied practice is a meaningful activity that might be understood through the concept of existential authenticity and, particularly with regards to long distance walking, might be 3 recognised as having components similar to that of pilgrimage. Furthermore, it is suggested that wayfaring offers an alternate perspective as a practice in the development of a particular relationship with landscape and place and has profound implications for outdoor pedagogic practice.