Existing digital technologies in urban settings tend to focus narrowly on concerns around wayfinding, safety, and consumption. In this paper, we examine pedestrian experiences based on the data collected through field observations as well as intensive interviews with nine pedestrians in the Shibuya area of Tokyo, and suggest an alternative approach to blending technologies and urban activities. Our focus is on social and cognitive aspects of pedestrians who get lost and explore a labyrinth of sidewalks. We use the data to discuss the activities that are often ignored or inadequately supported by existing systems.