Navigating an urban environment requires the brain to process complex sensory information coming from multiple sources (e.g., the body’s movement, noise, traffic, crowded places) and deal with multiple tasks at the same time (e.g., crossing the road while holding a conversation). As individuals grow old and develop functional limitations, they become more susceptible to the opportunities for, and challenges to, understanding and using their surrounding physical environment. Emerging studies suggest that urban places are more supportive than rural areas of cognitive health in ageing. However, little is known of which specific environmental characteristics (e.g., presence of green, walkability, architectural legibility) can help the ageing brain to adapt to a complex environment and contrast cognitive decline, while global ageing and urbanisation urge to identify factors in an urban space that facilitate and stimulate a successful interaction between an older person and his/her lived place. The present project defines and measures the subjective and objective characteristics of the outdoor urban environment that support cognitive well-being in older age by adopting a multi-disciplinary approach. We assess the environmental load on perceptual and cognitive processing in older age, and capture older people's subjective experiences of environmental sources of support for cognition in their day-to-day interaction with the urban space. Blending of an experiential methodology, walking interviews with older people in their neighbourhood, with quantitative approaches from experimental psychology and epidemiology is a unique feature of this project. The walking interviews illuminate perceptions of the city through experiences of journeying - the visual, sound and movement. This informs the quantitative study that examines the challenges and opportunities for healthy cognitive ageing posed by urban design complexity. Findings suggest that the city shapes cognitive functioning, and in turn, cognitive functioning shapes experiences and constructs of urban space arising from lifelong relationships with place.