Travel writing has been central to the American literary canon. From all possible backgrounds, origins and spaces, religious dissenters, immigrants and others have described their travelling experiences in North America. Within this profoundly American tradition, black Americans’ narratives are a special case. Most scholars agree that their personal accounts are not only autobiographical texts and political manifestos, but also travel narratives. Thus, the slaves’ journey is interpreted both as a physical experience—from the plantation to a free state—and a spiritual one—from ignorance into knowledge. After Emancipation, former slaves continued publishing their life experiences, and African American women became significantly active in autobiographical writing. These women challenged previous roles, and reinterpreted themselves as independent middle class entrepreneurs. Such is the case of the author analyzed in the present article: Elizabeth Keckley. Her journey from the plantation to Washington D.C. becomes an overt challenges to the racial and gender restrictions imposed upon her and gives wings to her desire for independence. Above all, the locations she inhabits while transiting from enslavement to middle class entrepreneurship inform this crucial transformation. By means of her transit, Keckley discovers her identity not only as female member of an oppressed race, but also as an individual who can achieve and prosper beyond the barriers imposed by (white and black) male society.