This paper emerges from joint research by scholars in South Africa and Germany on a literary trail devised in 2006 by the research project KwaZulu-Natal Literary Tourism. This urban trail, set in a historically Indian-occupied area of Durban, highlights writers who lived in and wrote about it. Coinciding with the tenth anniversary of the Grey Street Writers’ Trail in 2015, the literary trail was the focus of an MA dissertation by Bettina Pahlen on the relationship between the literature trail and ongoing urban renewal activity in the quarter.The research suggests that the Grey Street Writers trail represents a narrative of what trail designers, guides and authors consider meaningful about a place. Participant's engagement with this trail narrative shows its potential to change the perception of the area under regeneration. Informed by the work of Michel de Certeau (walking the city), Hubert Zapf (literature as cultural ecology), Throgmorton (storytelling in urban planning) and Edward Relph (placemaking, sense of place), this paper investigates factors limiting the trail’s contribution to urban regeneration in the Casbah. The questions asked by this paper is first, how the literary trail draws on and is impacted by experiences of urban renewal, and secondly, how the influence of the literary trail narrative on trail participants is limited by design and modified during implementation