Human curiosity never has a limit. It always occurs as people observe, stare at, and listen to whatever exists in the surrounding. In Old Damascus, as rich as a traditional city could be, sceneries always represent a variety of head turning situations, caused by attentiongrabbing stimuli where the essence or spirit of the place comes to mind. The spirit of the place is defined in this research as the expectation, unpredictability, surprise, attraction, invitation, or illusion that one experiences or perceives in streetscape. That is simply ascribed to six defined causes: observable urban elements; configuration of patterns; spirit of place; street layouts; the presence of sound; different light/dark alteration. These causes are explained and illustrated in the first part of the research. In the second part of this research, those causes had helped to understand head turning situations in examples from Old Damascene streetscape. Accordingly, classification of streetscape is possible with various attentive responses of a stroller’s reaction to different compositions of urban elements and street layouts.
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