In this paper we present the design and evaluation of Wandertroper, a mobile system designed to support re-engagement with everyday surroundings during daily walks. Wandertroper generates real-time sound based on the spectromorphology of the inhabited soundscape, which is manipulated by how the user walks. Through an iterative participatory design process using semi-structured group discussions and ‘in-the-wild’ evaluations, we outline how design aspects, such as the degree of output abstraction and aesthetic personalisation of use, facilitated users’ engagement with everyday surroundings. We discuss how Wandertroper turned daily walks into personally-meaningful aesthetic experiences.