The books starts with a strange event. The man wearing blue silk wings is standing on the roof of the hospital and cheerfully announces that he will fly to another side of the Lake Superior with his wings. He is an insurance agent named Robert Smith and he is clearly insane. The personnel of the hospital crowds below unable to do anything and sees as Robert plummets to his death clapping his useless fake wings. That night Ruth Foster Dead, the first black doctor in the hospital and in the whole unnamed town, gives birth to her son, Macon Jr. He is also the first black child to be born in Mercy Hospital.
The Deads are such a dysfunctional family as one can assume hearing their family name. The patriarch of the family, Macon II, is literally Uncle Scrooge. He is hated by his own family and almost by everyone who knows him and the only thing he cares is accumulating wealth. But still Ruth Foster has two other children from him: First Corinthians and Magdalene - the elder sisters of Macon Jr. Other family members are his aunt Pilate - the sister of Mason II and her own daughter Reba and granddaughter Hagar.
Despite the troubles in the family his mother and aunt love little Macon very much, up to the point that Ruth breastfeeds him until the age of four that is considered embarrassing in the society. After Ruth is spotted breastfeeding her son, Macon Jr. is forever nicknamed Milkman. Milkman is very interested in flights for unknown reasons, but when (at the same age of four) he understands that people are unable to fly by themselves in any way he seems to lose interest in life. He starts to resemble his father, cruel and indifferent Mason II more and more.
The time is skipped to the moment Macon is seventeen. He and his friend Guitar Bains are just average teenagers who drink beer, wreak havoc and court girls. But Macon sisters hate him for being cold, calculating and soulless, his mother became estranged and the only person who is still kind to him is aunt Pilate. Spending wonderful time in Pilate’s family, picking berries, walking and generally enjoying life, Macon falls in love with Pilate’s granddaughter, Hagar. Pilate is poor, but balanced and kind, she looks odd in the family line.
Later (well, the narrative is very scattered in terms of chronology, so let’s assume it’s “later”) Macon learns that his and Macon’s II cold behaviour isn’t totally his fault but a strange genetics that descends from their ancestors. He also discovers that his grandfather, Macon Dead got his odd surname when a drunken Union soldier made a mistake in his documents. Nothing is known about the real surname or about the given name of this man. He was killed when defending his land, while his children Macon II and Pilate saw that. That experience made them both mentally scarred and estranged from each other, but Pilate managed to cope with her trauma and live a happy life while Macon II lost his feelings almost completely and dedicated his life to accumulating wealth.
The story shifts to the period when Milkman is already thirty-one year old. He still lives with his family but Milkman is eager to change it and find another place for better life. He had a relationship with Hagar and broke up with her because he wanted a different future, not an ordinary one. Hagar didn’t take it well. She seemed to go mad and tried to kill him several times. While he is almost ready to give up his dreams about enormous wealth and adventures, his friend, Guitar, tells him something that just can’t be ignored. Guitar is a member of a secret society named the Seven Days. The members of this society kill a white bystander every time a black person is killed by whites, “avenging” their death in such a broken way.
Milkman is shocked. He is fed up with everything that happened to him and decides to leave once and for all. But then Macon Sr. again comes into play. He tells Milkman an equally horrifying story about him and Pilate killing some strange man in the cave far away when they were kids. In that cave they found a huge amount of solid gold in the green sack - very similar to the one hanging from the ceiling of Pilate’s room. Macon Sr. offers his son to steal it and divide the gold.
Milkman agrees (he is not a sensitive type at all) but instead of sharing the money with his father, he tells Guitar about the plan. Guitar is planning an especially tricky murder and needs money badly to fulfill his idea, so he eagerly agrees. The two men steal the sack first and run away… just to discover that sack was full not with gold but with human bones. Moreover, they are so inexperienced thieves that the police catches them almost immediately. The friends have to confess and then it’s Pilate’s turn. Why did the kind old woman keep the human bones in the sack in her room? Then they discover that the bones belonged to Macon I, Milkman’s grandfather.
Guitar is devastated and full of hatred. He hates Pilate for no reason (she didn’t have the money to steal!) he needs money badly and he was caught and interrogated by the police like an ordinary petty thief and not an elite assassin of super-secret society. But his friend finds a way to cheer him up. Milkman thinks that the gold may still be in the cave. He tells Guitar to catch him there and starts the quest for his origins.
He goes south from Michigan, guided by Pilate’s stories, and, after a long and exhausting search, which he isn’t prepared to, finds the right cave. But there is no gold also. Milkman has to try elsewhere. He goes to the small city nearby and occasionally finds an old midwife named Circe. She lives here for long and she knew Macon I and his two kids - actually she helped to deliver them. Circe tells Milkman that the real name of Macon Dead before the mistake of a drunken soldier was Jake and his wife was a native Indian woman named Sing.
There is nothing more useful to be learned here, so Milkman has a short rest and buys a bus ticket to Virginia, hoping to find there their old family house. The town of Shalimar that is his final destination, is small, quiet and lost in the middle of nowhere. Milkman is initially bored and irritated by its atmosphere. At first he is exceptionally socially awkward (he wasn’t very socialised in the childhood, remember?), insults the locals, gets beaten, makes conclusion and gradually starts to tolerate the town - and then to love it.
Milkman decides to go to bobcat hunting with his new friends in the town. Milkman isn’t a hunter, he is a pampered momma’s boy, so the walk and the hunt itself is incredibly hard for him. Exhausted, he suddenly becomes a prey himself. Milkman is traced and attacked by Guitar. His former friend tries to strangle him, without any apparent reason. Almost dying, Milkman finally grabs a gun he had for hunt and shoots Guitar, but misses. Guitar disappears in the forest but now Milkman knows he can’t be safe anymore. After finally shooting and gutting the bobcat the hunters (who haven’t noticed anything strange with their new friend and the assassination attempt) give Milkman some hints where to stay and who to talk to learn more about his family history.
Milkman returns to the town. He meets a prostitute named Sweet, a kind and simple woman. He stays in her house and has sex with her at nights and investigates his family roots daily. He finds Ms. Byrd, an elderly lady who is willing to talk, but doesn’t know where to start. When he returns to Sweet after his first day of searching, Guitar attacks him again. Now he bothers to vocalize the reason: all that time Guitar was thinking that Milkman have already found the gold and just don’t want to share as he promised. So now he wants to know where the gold is. Milkman fights back and repels Guitar again, but now he understands that his friend is totally crazy and isn’t going to listen to the truth.
Suddenly Milkman hears the children playing around and singing the song that Pilate sang to him. Finally he finds a clue to his origins. Next day he returns to Ms. Byrd asking her about the song and the conversation starts.
Milkman starts to gather the pieces of his family history and discovers that Jake descended from the African half-legendary hero Solomon, who built himself a pair of wings to fly away from slavery. Solomon tried to take Jake with him to fly away, but didn’t succeed. So he abandoned him, his wife Ryna and their more than twenty kids, escaping alone. Ryna went mad (just like Hagar in present) and her kids had to be adopted by strangers. Jake was taken by a man named Heddy, who already had a daughter, Sing. Later, stepsiblings married.
This story, though mythical, left a permanent scar on all the family members. They are destined to be who they are, with all their misfortunes, being emotionally dull, facing insanity after ruining relationships and the permanent desire to fly.
In the meanwhile, back in Milkman’s home, Hagar gets worse and worse. She convinces herself that she just wasn’t beautiful enough for Milkman. She constantly demands that Pilate sells her family ring with diamond and gives her the money. When Pilate finally does, Hagar buys herself fancy dresses, makeup and accessories - but she is so immersed in her delusions that doesn’t even notice that she returns home under a heavy rain. She enters the house frozen to half-death, shaking - but when her mother tries to warm her, Hagar finally notices that all her fancy outfits are completely and irreversibly ruined by water. She goes hysterical and locks in her room. Hypothermy causes a fever and, not willing to live anymore, Hagar easily succumbs to it, dying in mere days to Pilate’s unspeakable grief.
So, when Milkman, finally abandoning the search of gold, returns home with something more precious for him now - the family story - he is greeted with a bottle crushed over his head. Unconscious, Milkman is locked in his room by furious Pilate, who blames him for the insanity and death of her daughter. After a while, Pilate finally agrees to listen to him and she is warmed up to him after she hears the story. Pilate agrees to travel with Milkman to Shalimar and bury the remains of her father there, where he once belonged. They make a long way and indeed bury Macon I on the peak named Solomon’s Leap - the place from which Solomon flew away. But right after the burial Guitar shows up again and tries to shoot Milkman, hitting Pilate instead. The kindest and the most reasonable person in the whole story, the only one who managed to overcome the family curse is now dying in her nephew’s arms. The last thing we see in the story is Milkman, screaming Guitar’s name and leaping towards his enemy from the peak. The final lines are obscure, but it seems that his newfound origins finally gave Milkman the ability to fly. The family curse made a full circle and now can be broken.