This article responds to calls for the historical sciences to inform adaptation in the Anthropocene, in this case, the sustainability of hill farming in view of EU habitat conservation. Focusing on Kerry, Ireland, it highlights the difficulties that conservation of upland bog, heath and grassland habitats faces due to rural depopulation. It then uses landscape history to assess the long-term feasibility of conserving/restoring these habitats according to EU directives, pointing to the remarkably recent disappearance of woodland due to grazing and deforestation. Instead of being 'traditional', as conservation discourse holds it to be, historical management of uplands by farmers could vary greatly depending on socio-political factors and economic trends. I discuss how this historical ecology of change helps to explain the failure of conservation in parts of Ireland, and outline how 'lessons from the past' may contribute to sustainable upland management if co-evolution is accepted as an on-going process.