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Ever since Portland officials created Bayside out of earth and rubble in the 1850s, they have made changes to its physical landscape with limited, if any, resident participation in the process. Bayside, a small, urban neighborhood on the fringe of Portland, Maine’s downtown, has never been deemed worthy of deliberate planning efforts that engaged the entire community, and has become both an environmentally- and socially-marginalized area. Now, however, the city has proposed a new development known as Midtown, a large-scale project consisting of four towers and two parking garages, for West Bayside (the western half of the neighborhood). Based on research I conducted on the social and environmental history of Bayside, I argue that in order to avoid the mistakes of the past, those who seek to change Bayside’s landscape today must acknowledge the neighborhood’s multifaceted history and include residents of all types in the Midtown project and other plans for the neighborhood’s future. This strategy will enable Bayside to transcend the public perception that the neighborhood is only home to undesirable people and industry.