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This research intends to analyze how the social, political, economical and cultural transformations of the retrocession of Macao S.A.R. to China influenced the contemporary grassroots artistic production, namely their response to the issue of One Country, Two Systems policy. This transitional state of these places in-between creates a somehow ambivalent situation where some of the core values of identity and heritage are fading away due to the forces of the current development. In this sense, it urges to consider the ways in which artists in the post-retrocession era in their lived experiences, form their own sense of community and consciousness of place, time and belonging and, by doing so, can contribute to the preservation of some of the local and specific characteristics, enhancing the cultural vitality of the region. The growing interest by the artists in the issues of preservation and engagement with the locality, trough memory and history, manifested in ‘alternative’ modes of production, is providing a different model of ‘place making’ and a narrative that contrasts and complements some of the top-down cultural policies. Since the focus of development in these territories has been on the idea of creative industries, entertainment and tourism as possible realities for the pressing economical diversification, these grassroots models, functioning as the ‘second system’ open up complexity, providing different questions and answers to the future of artistic production. Finally, departing from these examples, we analyze the possibility of a new image for these kinds of artistic practices, through their incorporation into the possibility of relational aesthetics ‘with Chinese characteristics’, within the perspective of integration, and as emergent features in the field of contemporary art