This story takes its title from lyrics to the song sung at Ron Patimkin's graduation ceremony at Ohio State University in good old Columbus, Ohio. In Chapter 6, on the eve of Ron and Harriet's wedding, Neil gets to listen to what Ron calls his "Columbus record" (5.51), which is a recording of said graduation ceremony… which seems like a kind of a random thing to play such a major role in the story. Before that, in Chapter 5, Neil hears snippets of the record, coming from Ron's room at bedtime: "And so goodbye, Columbus, […] goodbye, Columbus…goodbye…" (5.142).
Neil doesn't know what to make of this at first, but it slips into the dream he has while staying at the Patimkins's house. In the dream, he and the "little colored kid from the library" (5.143) are on "an old sailing ship […] anchored in the harbor of an island in the Pacific" (5.143). Beautiful black women stand on the shore, but don't move until the ship begins to sail away from the island. As Neil and the boy sail away (against their wills) the women sing:
Goodbye, Columbus…goodbye, Columbus…goodbye. (5.143)
In the dream, the lyrics to Ron's song comment on infamous conqueror-explorer Christopher Columbus, poster child for the idea of seeking out new lands and conquering the people who live there. This is also known as colonization. This process is what led to the transatlantic slave trade and subsequent events that had a devastating impact on indigenous peoples and lands throughout the Americas and Africa. Yeah, that whole thing.
In wry irony, Neil has cast himself in the role of explorer-conqueror in Goodbye, Columbus. His "voyage of discovery" is from the crowded, poverty stricken city of Newark, New Jersey to the opulent suburbs of Short Hills, New Jersey. Short Hills is presented as an exotic paradise Neil seeks to conquer while claiming for his own "the king's daughter" (2.74), Brenda Patimkin.
In the dream, this collides with Neil's anxiety over the boy from the library, whom he views as a victim of not only the colonial past and of poverty, but also of current racism and discrimination at the hands of library employees and others. The book the boy reads every day in the library contains reproductions of the paintings of French artist Paul Gauguin.
In 1891, when Gauguin traveled to Tahiti, then a French colony, he began painting the beauty of the place and its inhabitants, and to some degree, the effects of colonialism. He incorporated native styles into his work, an act that is often thought to have revolutionized the art world. Still, Gauguin has his critics and has been accused of exploiting native culture and performing a kind of cultural colonization of Tahiti and the Tahitians.
In the dream, both Neil and the boy are being driven (by the boat moving on its own) from a Tahiti-like paradise. When the women sing "goodbye" to them it foreshadows Neil's being driven from the paradise of suburbia when he and Brenda break up. The dream also highlights the connection and identification Neil feels for the boy… that's quite the purposeful dream.