Riding Freedom repeatedly depicts characters who must make courageous choices even though they are difficult. First, we learn about Vern, who had to have courage to flee from slavery in the South. Then Charlotte chooses to run away from the orphanage rather than stay and be mistreated by Mrs. Boyle and Mr. Millshark. Not only does it take courage to make the decision to leave, but she needs to sustain that courage as she attempts to find work and lodging while hiding her identity. Later in the novel Charlotte, posing One-eyed Charley, relies on courage to get back behind the reins and relearn how to drive stagecoaches with only one eye. Finally, it is courage that leads Charlotte to the election polls to cast a vote that is technically illegal.

Charlotte exemplifies perseverance. She develops a dream for her life (owning her own horse ranch and living and working with Hay) and never stops working to achieve that dream. She also develops a plan to cast a vote to prove that women are just as capable as men, and she perseveres to make that happen. Although countless physical and emotional hurdles are thrown in front of her, she always pushes forward.