The first of three chapters on the power of chocolate cities, this chapter centers the life, activism, and pioneering efforts of abolitionist and black woman lawyer Mary Ann Shadd Cary. Exploring her migrations above and below the Canadian border, the authors highlight her sophisticated and politically informed racial geography of the United States. Detailing the movement of black people throughout the domestic diaspora, this chapter illustrates the how gender, place, race, and power collided in the lives of black people before and after the Emancipation Proclamation.