This paper reports findings from a research project, ‘Connecting Roots’, funded by the AHRC UK. Based on the learning from delivering six co-creation workshops to local communities, this paper discusses how design can be applied to support communities to collaboratively imagine future possibilities of health and wellbeing. It sits within the context of scaling up nature and nature based activities (e.g. park runs, community gardens) as a non-clinical approach for better health and wellbeing. These workshops aimed to address the challenge of inequality of access focusing on Walsall, a metropolitan borough in the UK exhibiting some extremes of deprivation, a lower than average life expectancy, and ethnic and cultural diversity. Findings from the workshops suggest that social imagination is central to addressing inequality, where people are empowered and supported to imagine what is possible for health and wellbeing, and communities. The design-led creative approach adopted in running these workshops has become a catalyst of new possibilities within social reality, through engaging people at a deeper emotional level and forging a collaborative culture and mindset, which has allowed people to express themselves openly and creatively, and to negotiate and develop shared community values collaboratively. The positioning of design in the context of community imagination and transdisciplinary research is emerging at present and it is suggested future research focuses on evaluating the longer-term impact of this kind of design-led approach for a better understanding of its potential.