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This paper explores parenthood and childhood in two gentrifying Boston neighborhoods by examining the narratives of parents who have raised or are raising children in the neighborhood. I argue that the collective choices of parent gentrifiers are defining the nature of cities. Their visions of an ideal neighborhood, middle class home, and most importantly childhood, shape both their struggles over space as well as their conceptions of what constitutes “urban” versus “suburban.” Already complicating expectations of suburbanization among middle class families, understanding how parents who remain in the city define the place they live is important in a moment where place labels increasingly shape strategies of economic development, and resource allocation. To begin, I start by considering the following question: How does gentrification shape the available narratives of urbanism and childhood? In addition to locating several generations of parents in two gentrifying neighborhoods, I find that these cohorts of parents are shaped by intensifying aspirations to establish urban environments as the ideal place to raise children. For some this is accomplished through efforts to bring elements of suburbia into their neighborhoods. However for others parenting and childhood are best realized far away from suburban environments. This ongoing construction of urban parenting takes place within the progression of gentrification in each neighborhood.