Drawing on interdisciplinary literature on urban walking, mobile media studies and sound studies, this paper explores how everyday walking is redefined by portable audio technologies. Above all, it considers how artists have reshaped mediated listening on the move since the 1980s, when the first Walkmans were launched on the market. I will discuss different artistic projects and suggest that many of these works infiltrate the dynamics between the walker and urban space by acting on the interference and hybridization between contextual and mediated experience, therefore breaking the "auditory bubble" (Bull 2007) created by headphone listening on the move. In particular, I propose three possible "tactics"-"revelation," "overwriting" and "interaction"-as permeable and overlapping ways to establish alternative behaviour, spaces and times that reinforce the potentialities associated with walking by creating micro-practices of aesthetic inhabitation of ordinary spaces.