The first group of Freedom Riders left Washington, D.C., on May 4, 1961. As many of their supporters predicted, the nonviolent protesters drew resistance that escalated into violence as the buses progressed further into Alabama. Yet even after the stoning and firebombing of one bus in Anniston and brutal beatings in Montgomery, civil rights activists were undeterred. Despite a request by Attorney General Robert F. Kennedy for a "cooling-off" period, new Freedom Riders arrived in Montgomery to continue the journey. The replacements boarded buses for Jackson, Mississippi, on May 24.

The strategy was intended to provoke a confrontation between U.S. Supreme Court opinion and state laws. The court had issued a series of rulings outlawing racial discrimination: the most recent, Boynton v. Virginia, had struck down discriminatory treatment in bus station restaurants and waiting rooms. At the same time, breach of peace laws in Southern states made the intentional disruption of public peace or safety a criminal offense. In the eyes of Southern segregationists, attempts to exercise civil rights such as those addressed in Boynton were examples of such breaches of the peace.

Attorney General Kennedy realized that under federal law, it was the Interstate Commerce Commission (ICC) rather than the Department of Justice that had the power to desegregate interstate transportation. When Kennedy's request for a cooling-off period was ignored by the Freedom Riders, he attempted to avoid further violence through negotiations with Mississippi Senator James Eastland, one of the most unyielding proponents of racial segregation. Eastland and Kennedy agreed that the Freedom Rides would continue, with local police and the National Guard protecting against further violence, but that, Supreme Court opinions notwithstanding, local officials could then arrest Freedom Riders upon arrival at their destinations for violation of local breach of peace laws.

The first Freedom Riders were arrested in Jackson, Mississippi, and sentenced to 60-day terms in the nation's most notoriously brutal state penitentiary, Parchman Farm. Despite beatings and other mistreatment, more Freedom Riders continued the demonstrations, with similar results. By summer's end, more than 300 Freedom Riders from as far west as California had been sentenced to Parchman Farm. For all of the brutality they encountered there, many viewed the experience as an opportunity to bond with other activists and share techniques of civil disobedience, turning Parchman into what some have called a university of nonviolence.

While the experience in Mississippi brought greater attention to the Civil Rights Movement, it was the ICC that officially ended discrimination in interstate commerce by issuing an order on September 22, 1961. This was a major victory for civil rights. It became clear to the nation, however, that Southern officials were determined to continue opposing the end of racial segregation. The enrollment of African American student James Meredith at the University of Mississippi the following autumn led to violent protests, and African American demonstrators were met with fire hoses and police dogs in Birmingham, Alabama, in May 1963. The cumulative effect of these events led President John F. Kennedy to request civil rights legislation from Congress in June 1963.

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