Compiled here for the first time are the works of Thomas Craige, Elizabeth Karr, Theodore H. Mead, and C. De Hurst, in an effort to see what it meant to be a horsewoman in nineteenth-century America. Exploring the acceptable ways for women to ride, dress, and interact with men while riding, these works expose social constraints on women in the horse industry. These texts work together to present the reader with both the obvious and subtle differences between horsemanship and horsewomanship during the century. Looking specifically at the creation of the sidesaddle and the significance of the habit, the reader can see how women were alienated from the equestrian world that horsemen occupied, bound up in constricting clothing and made to balance on horseback in an unnatural, compromising position. Regressing from the basic freedoms developed by the earliest horsewomen, American women of the nineteenth century adopted these sexist expectations and a role that rendered them male-dependent, even on the back of an extremely powerful animal often celebrated for its ability to liberate its rider.