This paper is a discussion of some patterns and elements of urban form seen in a historical perspective. It is an attempt to define the relationships between architectural design and history in the 21st century, taking into account different voices and points of view: the land, the buildings, the urban spaces, the architects, the inhabitants. Starting with the presentation and discussion of the dialogical model in architectural research, my contribution will show that, taking into account the complexity of relationships that have conditioned the configuration of the city, it is impossible to separate the physical and the social dimensions of architecture and urban planning. The main purpose is to evaluate the urban form of Morella through the dialogical model, analyzing the interactive relationships between design and environment. The historical core of Morella (Spain) is surrounded by old fortification walls, completely conserved until today. In recent years, some new public buildings have been built by Spanish famous architects outside the walled city. This paper focus our attention into the evaluation of contemporary design in relation to historic urban form, studying the configurative knowledge of architecture and planning, that is embedded into building and urban forms in a “generative way”. The purpose is to understand the meaning of the architectural design related to the problems behind, not only to the quality of architecture.