Social-ecological systems are complex, dynamic systems with strong interdependencies between their ecological components and the social actors that depend upon and shape them. They are characterised by resilience, multiple stable states and adaptive capacity and are constantly exposed to variable environmental conditions. These characteristics vary across space and time as does the supply of the ecosystem services they provide. Whilst such systems and their characteristics are well documented from a conceptual and theoretical standpoint, the quantitative examination of social-ecological interdependencies and their impacts on system dynamics has been less extensive. Furthermore, studies of historical service delivery are rare, as most provide a ‘snapshot in time’ of present-day service provision. The present study adopts an ‘evolutionary’ approach to explore long-term system change in the New Forest National Park, a complex social-ecological system with a millennia-long history of human-environment interaction. Palaeoecological records, historical maps, documentary evidence and instrumental records are used to examine past dynamics and ecosystem service provision in order to better comprehend contemporary processes and dynamics. There is a particular focus on the last 400 years and the Park’s ancient pasture woodlands. Dynamic system modelling is used together with historical records to examine in more depth the potential future evolution of these woodlands. Using this approach, we aim to answer the question: ‘Can the New Forest social-ecological system support multiple and potentially conflicting uses whilst remaining resilient to (undesirable) environmental and societal changes?’ Results show that when social and ecological influences have exceeded their historic range of variability, this has frequently resulted in drastic system change. Declines in traditional management practices related to the ancient commoning tradition, and a shift towards more intensive large-scale land-use strategies such as forestry, together with anthropogenic climate change and sustained high grazing pressure from Commoners’ stock, have been important factors influencing the extent, composition and structure of the Park’s habitats and its ancient pasture woodlands in particular. In the coming decades, continued high grazing pressure and extreme weather events are likely to be amongst the main challenges faced by the Park. These may lead to widespread regeneration failure in the pasture woodlands and, in the long-term, canopy collapse, opening up of the landscape, and a shift from woodland to grassland in some areas. These insights show the need to achieve a balance between multiple uses of this landscape and to consider the potential impacts of climate change in future management strategies.