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Shanghai is usually conceived of as a modern metropolis. Yet the city retains historical spaces, for instance the Yu Garden, first built in 1559. Literati gardens were created by the scholar-officials of dynastic China, known as wenren, intellectual elites well-versed in poetry, calligraphy and sometimes painting, while taking up positions in the government. Originally private spaces, these sites are recognized as cultural heritage and open to the public today, and could be seen as surreal spaces where past and present, dream and reality blend. Taking Shanghai’s Yu Garden as a case study, this article investigates how an anachronistic perspective of the surrealistic lens could connect the literati gardens to contemporary visitors and reveal values beyond their inherent ones as heritage sites. Via empirical accounts of my visits to the Yu Garden and briefly tracing the history of the site, I explored the surreality of the garden itself so as to provide the context. In the second part, I look at photographic representations of the Yu Garden with different creative intentions by the following photographers: Marc Riboud, Hu Jieming, Yu Wenhao and Dong Wensheng. Through visual analysis, I reveal how these representations chime with the surrealist discourses in different ways and how they bring about new ways to engage with historical sites. Having contextualized these contemporary representations, in the final part, I reflect upon my photographic practice. I make no apology for focusing on my own work, because my representation of the Yu Garden intends to evoke experiences not only of surreality, but even of transcendence, which will reclaim a space for spirituality much needed by Shanghai, the metropolis.