Stellenbosch faces the same challenges that most South African urban areas face: rapid urbanisation, sluggish economic growth, growing inequalities, unsustainable use of natural resources, deteriorating biodiversity, social problems, unhealthy living, insecure supplies of healthy food, degrading soils, infrastructure backlogs and inadequate urban planning. At the same time, Stellenbosch has tremendous potential. It brings together in one beautiful place extra-ordinary intellectual capacity, social diversity, financial resources, creative potential, high value eco-systems, spiritual energy and some of South Africa's most vibrant grassroots social movements in its poorest areas. The brief given to the writers was to examine the current challenges and discuss what needs to change in the way we think about these challenges to ensure more positive and sustainable long-term outcomes. This is, therefore, a contribution that aims to further open up and widen recent dialogues about the future that Stellenbosch deserves.