The research work, object of this paper, is included in the Fragile Territories project of the Department of Architecture and Urban Studies of the Politecnico di Milano. The province of Cremona where the research is handled is traditionally where rural areas confront expanding urbanization located in northern Italy. With the help of the GIS software, Cremona's current status was analyzed in terms of different qualities. The results revealed some issues that should be considered when representing and developing the landscape strategy, like quality of the green, water pollution, soil contamination, etc. Correlatively with these results, the proposed research and project development is aimed to represent the symbiotic relationship between the phenomenon of how different types of greens that serve different social and environmental functions work and harmonize with each other, connecting and enhancing landscapes that have been fragmented trough the wild urbanization happened after the second world war time. At the same time, this paper aims to demonstrate how the representation of new mobility connections might become a sort of fil rouge with the history of a place. In fact we need to rediscover the precious signs on the territory, existing before the wild industrialization and urbanization destroyed them after second world war, to go ahead with our designing proposals; this is the reason because landscape representation is a fundamental topic of our contemporaneity.