Homer takes the family on a "hate-cation" to Boston when he catches Bart rooting for a rival football team, the Boston Americans (a spoof of the New England Patriots). But after discovering the appeal of city, the family agrees to move there.
- Animal Athlete Loophole: Homer accuses the Boston Americans of cheating because they let their mascot score the winning touchdown, which they justify by stating that the mascot is listed on the player roster.
- Creepy Child: When the Simpsons return to Springfield, Lisa hallucinates herself still being in Boston, completely blinding herself from reality.
- Hollywood New England: Zig-zagged. The Boston American fans at Moe's are the stereotypes associated with the trope while the Bostonians the family meets in the city itself are more realistic.
- It's All About Me: Lisa doesn't care how miserable Bart is and wants to stay in Boston because it's perfect for her.
- That being said, Bart doesn't care that every other member of the family love Boston. It's not a crime riddled hell hole like he wanted, so he sets things up to force them to move back to Springfield.
- Perspective Reversal: At the beginning, Homer hates Boston while Bart loves it. But then Homer falls in love with it while Bart hates it. By the end of the episode, Homer hates it again.
- Southies: Averted. Bart is dismayed to find out how much the neighborhood has gentrified.Bart: This place is all PC brainiacs and Subaru owners wearing fleece vests. Its nothing at all like The Departed.
- Take That!: To the anti-vaccine movement:Marge: This town is so progressive. (sees woman walking her baby) Do you vaccinate your children?
Stranger: Of course!
Marge: But not stupid progressive!
- The Boston Americans are one to the New England Patriots and their fans.
- While at Quincy Market, Homer goes on a rant about how Fenway Park isn't as great a ballpark as Bostonians claim it is.
- Wrong Genre Savvy: Much like Homer's experience in season 5's Homer Goes to College, Bart discovers the hard way that Boston isn't the working-class gangsterland it's depicted as in The Departed and The Town.