One of the main issues of modern human geography is to discuss the process of spatial transformation and to explore how, through the interpretation of the humanities, the natural space presented its significance of the placeness. Although the landscapes of the city were aplenty and abundant, such diversity would easily make people form a blasé attitude and ignore the meanings hidden behind. Taking the spatial critical point, this essay tried to explain that the transformation of the urban space didn’t simply respond to the progress viewpoint of the modernity, nor was it just the consequence of the economical development. With regard to the correlation among the historical context, political economy, and the social factors, the transformation of the urban space was not only the production of the space, but the reproduction of the social relationships. Following the critical perspective, this essay tended to focus on the discussion of the Zhonghua Road. In the Chin-dynasty, this road corresponded with the city wall, which was closed space. After the regime shifted to the Japanese, to fulfill the exercise of power into a transparent space, it was necessary to demolish the wall; hence, a broad, straight, and modern road appeared in the Taipei City. After 1949, a number of refugees from mainland china needed the transit camps in Taipei after the war. Thus, at that time, along the railway in the Zhonghua Road appeared many temporary shelters for squatters. After a decade or so, the disorder of the space was noticed by the authority concerned; hence in order to solve the problem, the spatial transformation was made by the rehabilitation of the Zhonghua Bazaar in the same space, which turned out to be the most prosperous place in Taipei in the 1980s. As time went by, the renovation of the city was probably necessary for the growth of the population and the traffic. Under such viewpoint, an imaginary, aesthetic, and leafy shade road was built to cater for the modern planning in Taipei city. The urgent task is to explore the implication of the space hidden behind and the research will help us face the grotesque modernity with more accurate perspectives.