This article explores how walking in a particular type of terrain, the moorland area of north Derbyshire known as the Dark Peak, contributed to a localized sense of place which was framed by regional and national discourses and also testified to broader social and cultural uncertainties strongly shaped by gender and class. The punishing physical values of such wild upland areas offered challenges of stoicism, hardiness and endurance which were central to late-nineteenth century ideals of manliness, as masculinity was increasingly defined by forms of sporting activity which encouraged character-building battles against nature. Sensibility is not readily associated with this robust discourse of adventure. The ‘wild’ outdoors, so easily seen as an extension of the public, masculine world was, however, of far greater complexity. More than a focus for physical activity and trespass ‘battles’, it was a place where emotion and the elating intimacy of open space gave expression to needs which also intimate the masculine anxieties of the era.