The linear public spaces were recognised as one of the five key elements that form the image of the city by Kevin Lynch. He studied the characteristics of memorable paths and argued that the paths with clear and well-known origins and destinations have a stronger identityIdentity, as well as that paths may become important features to the residents in several ways such as customary travel, the concentration of special use or activity along the edges, specific spatial qualitiesSpatial quality or special facadeFacades characteristics. However, some contemporary studies show that new information and communication technologies profoundly change the ways we perceive our living environments. This chapter addresses the heterogeneity of the two images of a concrete road – one formed based on the lived experience of space and one formed through the consummation of the information accessible on the world wide web. The two images are studied on the case of Celovška cesta (Celovec Road) in the Slovenian capital city of Ljubljana, which is a 6-kilometer-long historical main access road that connects the Alpine region of the country to the city center. The edges of the road were built up mainly after WWII in socialist times when the modernist urban planning paradigm was in place. The study shows that the characteristics of the virtual image of the road largely differ from the image revealed by classical urban design analytics. The theoretical and practical implications for urban designers are discussed at the end of the chapter.