This article aims at investigating the conditions older people face when walking through their neighborhoods. It seeks to identify the ways in which the built environment, the socio-spatial features of the neighborhoods, and the COVID-19 pandemic affect their walks. To that end, the article reports the findings of a set of interviews and focus groups where older people who reside in four neighborhoods located in the Commune of Santiago, Chile, were invited to talk about their walks and the obstacles they face when taking them. The findings show that older people consider walking a highly beneficial activity whereby they remain active, connected, and visible. They state that the processes of change that have affected their neighborhoods have transformed their landscape and social architecture, increasing fear of the public space and the feeling of loneliness. The analysis of the data also showed that older people face many obstacles when walking, including sidewalks in disrepair, hostile pedestrian crossings, and unpleasant landscapes. Those obstacles were multiplied by the arrival of the new coronavirus, which added restrictions and concerns that make walking even more difficult. The data gathered emphasizes the relevance of walking for older people, making the creation of walkable neighborhoods and their promotion in the public policies as a practice of self-care, crucial.