Nostalgia has historically been negatively characterised by desire to reconnect with an idealised past lost to the ‘destructive’ forces of modernity, but studies across the social sciences have recently sought to re-appraise the creative and embodied significance of individuals’ recollections. This paper contributes to this developing debate by empirically exploring the value of individual remembering in relation to the urban material landscape. First, drawing on recently collected go-along data from long-term residents of two UK cities, Birmingham and Coventry, it is argued that nostalgia could be considered a more progressive force in urban life, especially amongst residents in cities that have undergone and are undergoing physical change as a consequence of ‘official’ attempts to reconstruct, regenerate and/or repackage particular urban spaces; developing a richer understanding of the interplay between official and unofficial nostalgias can better inform planning decisions that are more likely to be socially acceptable and supported by local communities. Second, though there are clear advantages of developing a fuller theoretical and methodological consideration of urban nostalgia, this paper then uses go-along data to demonstrate that much remains to be learnt from exploring how the material urban environment can encourage and/or limit individual efforts to keep potentially distressing aspects of their past concealed.