The purpose of this work is to study the evolution of these views in a growing city, paying special attention to the city-countryside dialogue. Madrid is chosen as the study case, as part of a funded project entitled “Proximity Landscapes of the city of Madrid. From the 19th Century to the present.” This research tackles Madrid's urban contour and surrounding nature: an area that has been left out both by regional and local environmental studies. Through the analysis of historical cartography and other documentary evidence, we detect the areas of urban-rural friction along Madrid's contour line in five relevant stages of the city's development. The main conclusion drawn from this study is that lookouts from the city towards the countryside show a higher permanence, while the relevant observation points looking into the city not only move further away from the urban contour line, but proliferate as potential places from where to apprehend the iconic image of the city.