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The urbanization of recent decades has radically changed the original morphology of territorial systems. Recognize the traces of long-term urban form, on a large scale, can help land planning actors in order to make settlements more sustainable and resilient. The aim of the paper is to analyze the long-term urban plan for the territory of Albenga area, in the Western Liguria, Italy. Settlements are analyzed together with the basic territorial structures that have generated them during the historic long period. The study starts from the diachronic reading of cycles of territorial development that have gradually formed the present settlement. The matrix elements that determine the shape of the settlements are, in the first instance, the paths and the plots (including land uses), detectable by comparing different historical maps. Subsequently the different built forms are classified into “morpho-territorial typologies”. The representation of the settlement into different temporal stages is the result of processing carried out through the use of GIS and simulation models based on cellular automata and multi-agent systems. Through geosimulation techniques it is possible to rebuild both the process of formation and transformation of the settlements, and to represent the structure of long-term of “morphotypes”. The use of geosimulation techniques also allows the construction of scenarios in which it is represented how the process of urbanization of the last 50 years has radically altered the original settlement structures and also allows us to represent the possible evolutions of the settlement system.