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 game between the Springfield Atoms and the Boston Americans, but they are 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 outraged at the Boston team that he says of losing his love of football if he sees a Boston fan, but seconds later, he is surprised to see Bart wearing a Boston Americans' cap.
Homer gets ticked off at Bart, but plans to take him around Springfield for encouragement to cheer for the home team. Bart refuses and admits that people in 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.
In Boston, Homer starts provoking the Bostonians, when a cart full of bobbleheads fall on him. Then he is 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 city's recreational areas and education system, which also impresses them, especially Lisa.
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 to 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 city.
The Simpsons rent an apartment and move all of their possessions 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 the kids in detention analyzed their energy into a Capella song, the roads are too bumpy for him to ride his skateboard, and that most of the town is for intellectuals like Lisa. At dinner, he tries to convince the family to move back, but everyone is satisfied with where they live. While on the roof Lisa tells Bart that she had to suck up her desire to move to a city like Boston and now it was his turn. 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 rage, but he gets irritated when asked to put on a Boston Americans' cap, ripping it in half and shouting that they are cheaters. The Simpsons then have to move back to Springfield, where Marge gets sore at Homer for making them lose that opportunity, Bart is now wearing a Springfield Atoms' cap and Lisa is hallucinating about Boston.
This episode was nominated for an Emmy Award in June 2017 for the Outstanding Animated Program.