This paper is an inquiry into debates around: Englishness; rural nostalgia and the anti-development narrative surrounding landscapes of ‘cultural significance’ and ‘natural beauty’. The text’s particular focus is structured around how these decisions are cultivated and impose a specific societal response to the landscape of Dedham Vale. It charts how these passive inferences have been imbedded in legislation for the last one hundred years and explores the current political debate around reviewing their ethical and practical legitimacy. The inquiry is underpinned through challenging the traditional reading of landscape and artistic practice through the paradigm of Constable’s paintings, which inform past and current positions on landscape preservation and cultural management. The country’s contemporary geopolitical landscape is examined through the prism of new nature writing and artistic practices, both of which provide an alternative model for establishing a new awareness of ‘landscape’.