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F. Scott Fitzgerald made deliberate, artistic choices in depicting the Midwest. In The Great Gatsby, he chose “Little Girl Bay” as the setting for James Gatz’s transformation into Jay Gatsby on the shores of Lake Superior. Fitzgerald’s setting is based on Little Girl’s Point on Michigan’s Upper Peninsula. Historic information about this frontier setting illuminates Gatz’s transformation and grounds his traits in regional history. This article explores the setting’s proximity to logging and mining camps, infamous turn-of-the-twentieth-century Hurley, Wisconsin, saloons and brothels, and the confluence of immigrant newcomers and indigenous people. It places significant focus on Henry R. Schoolcraft’s Ojibwe folktale “Leelinau, or The Lost Daughter” as the basis for the name of Little Girl’s Point as handed down by Schoolcraft’s wife, Bamewawagezhikaquay (Jane J. Schoolcraft). The tale, which parallels motifs in The Great Gatsby, tells of a young maiden who runs off with her fairy lover. At night her moonlit figure is seen on the shore by fishermen across the waters. When they approach, she flees, sheltered by her lover’s green plumes.