This paper is about how rural landscape is experienced according to combinations of practical engagements with land and the ways meaning is made in relation to it. It presents the case of the ambiguous position of the Orkney Islands within categorisations of Highland and Lowland landscapes in Scotland. Through a discussion of the physical and highly visible boundary between heather and grass in Orkney farms, the paper unpacks notions of what landscape means and how it fits with socio-economic processes of continuity and change. It uses the history of hill reclamation in 20th century farming to explore how economic, moral and aesthetic judgements are made about land. Current engagements with hill land are then examined, showing how a fragmentation of hill into different uses and meanings is taking place. Amongst these are agri-environment schemes which revalue the hill. The paper ends with a discussion of hill land and farm land in Orkney in relation to the wider construction of Highland and Lowland. In Orkney opportunities to construct new ‘Highland’ identities and forms of rural development now exist.