After Homer catches Bart rooting for Springfield's football rival, the Boston Americans, he plans a family "hate-cation" trip to Boston in an attempt to show Bart that Boston is a terrible city.
Homer goes to Moe's to watch the football match between the Springfield Atoms and the Boston Americans, but they're surprised by Boston fans. They start mocking each other, but at the end of the game, the Boston team wins by a touchdown, made by the mascot. Homer is so ticked off at the Boston team that he says that he's going to lose it if he sees a Boston fan, but seconds later, he is surprised by Bart wearing a Boston Americans' cap.
Homer gets angry at Bart, but he plans to take him around Springfield to encourage him to cheer for the home team. Bart refuses and admits that people at Boston are his people. Homer gets so traumatized by this that he starts hallucinating about the Boston team, so he chooses to take the family on a "hate-cation" to Boston to show Bart what a terrible place it actually is.
At Boston, Homer starts provoking the Bostonians, when a cart full of bobbleheads fall on him. He's helped by lots of doctors, and they learn about the city's healthcare which impresses the family. Later, Marge, Lisa and Maggie go explore Boston on their own and learn about the town's recreational areas and education system, which also impresses them.
Meanwhile, Homer and Bart go candle pin bowling, with Homer claiming that "they even found a way to mess up bowling". Bart encourages Homer to try it, and for their surprise, he likes it. Homer then gives up on the hate-cation and plans to enjoy Boston with Bart. Back at the hotel, Marge and Homer talk about their experience in Boston so far and chooses to move to the town.
The Simpsons rent an apartment and move all their stuff to Boston. Homer finds a job at a candy factory and Lisa enjoys the local school. However, Bart realizes that he can't keep his prankster career anymore, as kids in detention analyzed their energy into a Capella singing, and that most of the town is made for intellectuals like Lisa. So he plans to find a way to make the family move back to Springfield.
Bart takes the family on a parade in honor of the Boston Americans for another game they won by cheating. Homer tries to control his anger, but he gets enraged when asked to put on a Boston Americans' cap, ripping it into two and yelling that they are cheaters. The Simpsons then have to move back to Springfield, where Marge gets mad at Homer for making them lose that opportunity, Bart is now wearing a Springfield Atoms' cap and Lisa is hallucinating about Boston.