As you walk west, and just after you cross 135th Street, notice the Big Apple plaque on the side of 2300 Adam Clayton Powell, Jr., Boulevard. Beginning in the 1930s, this building housed the Big Apple Restaurant and Jazz Club. In recognition of its status as a center of jazz, musicians dubbed New York the "Big Apple." The phrase stuck as a moniker for the city as well as for this club, although research has also turned up references to the city as the Big Apple in horse-racing columns two decades earlier.

To your left, across the street, you will see what was 220 West 135th Street, the former home of Florence Mills, one of the most popular singers and dancers of the 1920s. An international star, Mills performed on Broadway as well as in productions abroad. Hoping that her success would make "people think better of other colored folk," Mills passed over an offer to perform in the Ziegfield Follies in order to participate in an all-black revue. Mills was a true pioneer, paving the way for other black women entertainers such as Josephine Baker. She died of appendicitis in 1927, at the age of thirty-one. Her funeral was the largest in Harlem's history: more than 5,000 mourners filled Harlem's Mother Zion AME Church for her funeral service and more than 150,000 followed the funeral cortege through the streets of Harlem. At the cemetery, a low-flying plane released a flock of blackbirds as a final goodbye.

Right next door is 224 West 135th Street, the former headquarters of the NAACP, now Flo's Beauty Salon. The interracial NAACP, formed in 1909, has historically fought, through judicial and legislative channels, for voting rights, integration, and equal educational and economic opportunity for African Americans. The Crisis, the monthly publication of the NAACP, had a circulation of more than one hundred thousand by 1920. Edited by civil rights leader W. E. B. Du Bois from 1909 to 1934, The Crisis was one of many important periodicals produced in Harlem in the early twentieth century.

The NAACP's Legal Defense and Education Fund, established in 1939, would go on to try the landmark Brown vs. Board of Education case of 1954. Legal Director Thurgood Marshall's argument before the Supreme Court led to nationwide school integration and sparked the legal phase of the civil rights movement. In 1965, Marshall became the first African American justice to be appointed to the United States Supreme Court.