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When the book opens, Gypsy Arbutus Leemaster, the main character, is talking about how her Aunt Belle just up and disappeared one day. She just walked out of her home and was never seen again. Because of this, Gypsy's cousin Woodrow—a cross-eyed boy who is the same age as her—comes to Coal Station to live next door to Gypsy, her mother, Love, and her stepfather, Porter. He's going to stay with their grandparents for a while since his father can't take care of him by himself.
Gypsy and Woodrow become fast friends and start hanging out all the time. They like going to the movies and spending time in Gypsy's tree house, which her father, Amos, built for her before he died. Woodrow's grown up in poverty, so he loves Coal Station and all the new things that he gets.
Woodrow likes Coal Station so much that he wonders why his mother ever left this place. Granny tells Gypsy that Belle left because she was so jealous of her sister. It turns out that Amos was Belle's sweetheart first, but he fell in love with the gorgeous Love as soon as he saw her. She says that Gypsy is like her Aunt Belle in personality and piano-playing abilities but that she looks like Love—she is beautiful and has long, luscious hair that she's not allowed to cut because her mother promised Amos before he died that she wouldn't cut Gypsy's hair.
Woodrow goes to Sunday school with Gypsy and meets some of the kids from their school. Even though he looks different and has a tragic backstory, the kids all like him because he tells these funny, interesting tales. The only person who seems upset is Buzz, who is basically the school bully. He's mad that Woodrow is suddenly getting so much attention.
Woodrow goes to school and joins Gypsy in class, where he's equally as popular. One day, he and Gypsy decide to go to the movies, but Porter comes along—even though it's obvious that Gypsy doesn't like him and resents him for taking her father's place. The movie is Rear Window, and when the actress looks through the window, Gypsy starts screaming at her to not look inside.
Gypsy faints and Porter has to carry her all the way home. She has a bad fever and hallucinations, and when the doctor comes, he announces that she has the measles and will need bed rest for a while. Ugh.
During Gypsy's convalescence, she constantly has a recurring nightmare—one where she looks through a window to see an animal lying in a pool of blood, its face unrecognizable. When Gypsy feels a little better, Woodrow brings Blind Benny, the blind man who wanders the town at night, to her window so that he can sing to her. He says that her father always used to bring Gypsy around to see him, and that Amos didn't treat him any differently because he was blind.
When Gypsy is well again, it's already summer vacation. She spends a lovely summer hanging out with Woodrow and playing outside, though she's still having the nightmares and Aunt Belle hasn't come back yet.
Love throws her annual garden party, and Gypsy and Woodrow are charged with serving all of the ladies. The principal's wife, Mrs. Cooper, starts acting like a jerk to Woodrow and telling him that she always knew his mother would amount to no good. Woodrow tells her that he's slipping rum into her drinks—even though he's not—and she thinks she's drunk and goes splashing into the creek. Gypsy gets upset when the whole family thinks that what Woodrow did is funny instead of punishing him like they would with her. She feels frustrated that everyone likes Woodrow for his personality when they just see her as a pretty girl.
Gypsy and Woodrow start fighting, and things are awkward between them after. On the first day of school, they still haven't made up. When they get to class, though, the teacher asks them about themselves, and Gypsy says that her father died in a fire when she was a little girl. He went in to save a baby and died in the line of duty.
Buzz pipes up to say that she's lying—her dad didn't die in that fire. He knows the truth, which is that Gypsy's dad was badly scarred in the fire and he couldn't take it anymore… so he shot himself in the face. That's when Woodrow jumps in and starts beating up Buzz. Gypsy walks home in a daze while remembering what happened, and how she looked through the window as a little girl to find her father dead in a pool of blood. She was the one who found the body. No wonder she screamed while watching Rear Window, right?
When she gets home, Gypsy suddenly feels furious at her father for leaving her like that. She grabs a pair of scissors and starts hacking off all of her hair. Porter comes in and tells her that it's okay and that he sees her for who she really is—that she's talented and smart and hurting, that's all.
Gypsy feels bad for being so mean to him all this time, and Porter promises that he'll talk to her mom about her hair so that it's not a shock. Later, Gypsy goes to the barber and gets her hair cut into a pixie cut. When she returns to school, she pretends that she absolutely loves her hair and that she got it cut because it's the latest fashion in New York City… and the other students actually believe her. In fact, a bunch of girls show up at school with the same haircut the very next day. Nice.
Gypsy and Woodrow sneak out at night to go with Blind Benny on his rounds. He tells her that he lives in a room in the hardware store that her father used to own, and that it's thanks to her parents that he's not living out on the street. They told him that he'd have a place to sleep and food to eat at the hardware store for as long as he lived, and Gypsy is touched by their generosity.
Back at home, things return to normal. One day, though, Porter announces that he has two surprises. One is the fact that he's going to take Woodrow to a specialist to see if he can get an operation to fix his eyes. And the second is that they're going to organize a piano recital for Gypsy since she's so talented. Finally someone is recognizing her for her talents and not just for her looks. They're all thrilled.
Later, on the one-year anniversary of Belle's disappearance, Gypsy and Woodrow meet up at dawn to go to the tree house. Woodrow tells her that when Belle went missing, he found that some of his clothes and shoes were gone, too—and that he thinks that she left town dressed as a boy.
He's hurt that she hasn't come back for him or taken him with her, but he understands why she had to go; she was just so unhappy with her life. Gypsy realizes that she forgives her father for committing suicide; too—after all, he was hurting so much. They sit there together and watch the sun come up, feeling at peace at long last.