This paper explores a novel application of the Literary Method of Urban Design to predict and shape the future forms of three new “case study” towns set in Wales: Swansea, Gilfach Goch and Dinas Mawddwy. This method uses literary works to create “design fictions”. These design fictions aim to provoke debate about potential future opportunities for towns and cities and potential future problems for towns and cities. The three novel case studies explored in this paper are variously inspired by Alan Garner’s novel The Owl Service, Richard Llewellyn’s novel How Green Was My Valley and Dylan Thomas’ poem The Force. Each case study invokes a graphic representation - in the form of scenario art - which visually narrates a future shaped by the themes of the respective works: so transforming the town of Dinas Mawddwy into an urban woodland, reimagining the town Gilfach Goch as a post-industrial paradise and harnessing natural forces to create the living city of Swansea. This approach attempts to consider the vagaries of human characters within unpredictable and dynamic ecologies and social structures but which also integrates cultural and aesthetic dimensions into the art and practice of urban design. The emerging scenarios underscore the potential value of considering artistic methods with qualitative narratives and historical insights to achieve a potentially more holistic understanding of future urban developments - at least in the land of legends and stories that is Wales.