In the 1920s and 1930s, within a stone's throw one could find the headquarters of the NAACP (National Association for the Advancement of Colored People), the National Urban League, and the Universal Negro Improvement Association, all sites we will see later in the tour. Also closeby were the offices of the major black newspapers—theconservative Amsterdam News and the more militant New York Age—the New York Public Library, and the YMCA (Young Men's Christian Association). By 1920, Harlem had become New York's primary African American neighborhood, and most black political and social institutions had moved here by that decade.

The YMCA is located at 181 West 135th Street. Founded in 1851 to provide moral and spiritual guidance to young male migrants from rural areas, the YMCA's membership and outreach efforts were restricted to white men until 1867. A "colored men's branch" of the Y opened on West Fifty-third Street in 1900, to serve the needs of migrants from the South. It moved to this location in 1919. So great were the demands on the services of this YMCA that an annex was built across the street in 1932.

This particular branch of the Y also served as a hotel for black visitors to New York City who were denied access to the segregated hotels elsewhere. Among its guests were Ralph Ellison, Langston Hughes, and James Baldwin. During the Harlem Renaissance, the literati met here to exchange ideas. The YMCA's Little Theater program started the careers of actors such as Sidney Poitier, Eartha Kitt, Cicely Tyson, and Danny Glover. Other patrons of the Y who would go on to prominence include Jackie Robinson, Richard Wright, Paul Robeson, Jesse Owens, Bill "Bojangles" Robinson, and Willie Mays.

Although the building is empty now, at 2294 H Adam Clayton Powell, Jr. Boulevard, on the southwest corner of 135th Street, was Ed Small's Paradise, one of Harlem's most popular jazz clubs and restaurants from the 1920s to the 1940s. Those who could afford the prices at the "Hottest Spot in Harlem" would be treated to music, elaborate floor shows, and singing waiters. The small dance floor at Small's Paradise got so crowded that each patron was said to have a dime's worth of floor space for dancing. A young Malcolm Little, after losing his job as a waiter here, began a downward spiral into criminality that eventually landed him in jail. There he converted to Islam and changed his name to Malcolm X. In the 1960s, basketball star Wilt Chamberlain reopened the restaurant as Big Wilt's Small's Paradise.