Recent times have seen much reflection on the nature of the Anglo-Scottish border region; its past, present and potential future. Political concerns have rightly absorbed much of the attention, but at the same time important light has been shed on the legacy of cultural engagements and forms of interaction that might be said to perform and produce this border over time and render it particularly distinctive. A soft, internal border, the territory considered in this article is one with an ancient feudal past and a heavily conserved, preserved and, in parts, still militarized present. It is predominantly rural and characterized by large swathes of forestry, agriculture, and moorland, all of which raise issues of aesthetic and environmental, as well as social and economic sustainability. The concern in the case studies presented in this article is how, through the relational and processual perspectives of border studies and cultural landscapes, we might comprehend the over layered and sedimented histories, the nature of identities, heritage and experience of place here. I consider too the ways in which recent forms of creative practice are contributing to a wider investigation of this region and re-conceptualizing the cultural significance of the border.