The wide adoption of mobile devices and streaming music services has paved the way for location-based music services. However, there has not yet been any commercial breakthrough. We designed OUTMedia, a location-sensitive music discovery application with unique features, to explore rewarding user interactions. This article reports the design efforts and a field study of the functional prototype. We utilised user interviews, log data and the ResQue instrument to study use and user experience of the prototype. All measures found the overall concept feasible and the use of the application resulted in serendipitous experiences of music and places. Our findings call for service designers to support the interplay between media and places in personal meaning-making processes, to enrich urban cultural experiences with user-created information layers that accumulate over time. The design implications can be used to support serendipitous music experiences through the interplay between places and media in future content discovery services.