Scholars have identified several elements related to the physical surroundings that positively contribute to psychological wellbeing during walking. Among these, the benefits of natural elements have received extensive attention in the literature. However, we live in an increasingly urbanised world, hence opportunities to visit green spaces are limited for most urban dwellers. This is why it is increasingly important to explore the characteristics of current built environments that might support psychological wellbeing during walking. This mixed-methods research examined wellbeing outcomes of walking in different settings, and how they relate to their perceived tangible and intangible qualities. Settings consisted in five non-residential urban settings of Bristol (UK) city centre: a) a pedestrianised historic street, b) a pedestrianised modern street, c) a pedestrianised street with green and historic elements, d) a commercial street with traffic and e) an urban park. Methods included an experimental study with adults living and/or working in Bristol based on a video-simulated walk, and 15 semi-structured photo and video-elicited interviews with a sub-sample of participants. It was found that walking in pedestrianised settings with little or no nature can support mental wellbeing too, as it reduced stress and triggered hedonic tone. Psychological wellbeing and cognitive recovery were predicted by place perceptions on settings' functionality (e.g.: quality of walking infrastructures, absence of traffic), cultural significance (e.g.: characterness, authenticity) and personal connectedness (e.g.: memories, place attachment and identity). These results reveal important implications for urban designers and active travel practitioners.