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Designing a novel approach to existing art collections requires a shift in perspective. Computational approaches allow for an agnostic approach to cultural assets—akin to distant reading—,affording a capacity for embracing estrangement as a fertile design strategy. This paper investigates the potential convergence of these fields through the lens of machine curation and audience engagement, specifically examining the influence of contemporary machine learning models on curatorial methodologies. This investigation takes the form of a project conceived for the 2023 Helsinki Art Biennial and as a collaboration between the Centre for Digital Visual Studies (MPG, University of Zurich) and the media artist Yehwan Song, aptly titled Newly Formed City. Exploring the art collection of the Helsinki Art Museum (HAM), we seek to reinterpret the cityscape of Helsinki through a machine-oriented perspective. Utilising visual-textual models, we relocate unexhibited artworks to public locations, where, through the creation of context-based computer generated 360-degree panoramas, artworks are placed. Consequently, the outdoor sites are changed by the presence of the artworks, creating a new speculative geography where the city and its art collection are visually fused together. Interaction is achieved through a web interface, offering visitors the opportunity to move through an alternative version of the city and interact with its cultural heritage on a large scale, exploring the capacities for creativity located at the crossroads of a reflective exchange between vicinity and ignorance, machinic analytical prowess, and the uncanny and the unexpected.