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On May 4, 1961, an interracial group of six boarded a bus at the Greyhound station at 1100 New York Avenue, NW, while another six people boarded a bus at the nearby Trailways station. The purpose of the planned Freedom Ride to New Orleans was to test the 1960 U.S. Supreme Court decision in Boynton v. Virginia,which reiterated an earlier decision prohibiting racial segregation in interstate transportation.

On April 30, 1961, John Lewis (of the Nashville Christian Leadership Conference) had arrived in Washington to join 12 other Freedom Riders in preparing for May 4, the day groups would embark from various cities in a series of Freedom Rides organized by the Congress on Racial Equality.

CORE had solicited applications for volunteers for the first ride and received about 50. CORE staff chose a racially diverse group of men and women ranging in age from18 to 61 and representing various regions and backgrounds. James Farmer, CORE's executive director, and James Peck, a radical white journalist who acted as CORE's chief publicist, would be two of the riders.

The group stayed at Fellowship House, a Quaker meetinghouse and dormitory at 945 L Street, NW, where they underwent orientation for the ride. This included role-playing exercises, presentations on the culture of the Deep South and federal and state laws regarding discrimination in interstate transportation, and training in nonviolence and what to do in case of arrest. They agreed not to seek bail if arrested but to serve out their terms. Volunteers were free to back out, without being stigmatized, of what would surely be a dangerous journey.

The next morning the volunteers split into two groups; half to leave from the Greyhound Bus Station, then at this address, and the other half to leave from the Trailways Bus Station at 12th and L Streets, NW. Three journalists joined the ride, and a fourth planned to join them in Greensboro, North Carolina.

The women participants wore dresses and heels, and the men wore coats and ties. Farmer encouraged them to think of themselves as teachers and role models, and to mingle with the other passengers on the buses. He had also instructed them to pack a few items, including books, that they would need in jail if arrested.

The departure was uneventful, but five days later the Riders encountered violence at the bus station in Rock Hill, South Carolina, when black riders attempted to use a "whites only" restroom. The trip continued through Georgia without incident, but the Greyhound bus was firebombed in Anniston, Alabama. No one was injured, however. The Trailways bus made it safely to Birmingham, but in that city the Freedom Riders encountered intense violence – and the end of the bus trip after drivers refused to continue. Some of the group did reach their New Orleans destination, but they arrived there via Eastern Airlines.

The Freedom Ride movement expanded and new groups continued riding buses through the end of 1961. Many of the riders spent weeks in jail.

Having received international attention, the rides forced U.S. Attorney General Robert F. Kennedy to petition the Interstate Commerce Commission to enforce the prohibition against discrimination in interstate travel. An ICC order imposing penalties for ignoring the prohibition went into effect November 1, 1961.

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