Tropes:
- Arc Words: Homer and Marge call the family's impulsive decision to relocate to Boston their "third ball," referring to the discovery that first endeared Homer to the town—the fact that candlepin bowling allows three balls per frame, meaning an unexpected second chance at victory for someone accustomed to standard bowling.
- 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.
- Artistic License – Sports: Registered on the team roster or not, the mascot receiving a pass would never fly. But the absurdity is part of the joke.
- Creepy Child: When the Simpsons return to Springfield, Lisa hallucinates herself still being in Boston, completely blinding herself from reality.
- Foreshadowing: Bart mentions that Boston is a "bad-boy" town, like him. Later on, it's revealed that he only liked Boston for its crime rate, and becomes unhappy at how peaceful and education-friendly it really is.
- 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 in Boston and wants to stay in the city because it's perfect for her.
- That being said, Bart falls into the exact same trope and is much more selfish about it. Initially, he's the one most excited about moving to Boston, but when it's revealed to not be the crime riddled hell hole he imagined, he does something of a Heel–Face Turn and sets things up to force them to move back to Springfield. The rest of the family has come to love the city, and when Lisa says Bart is jeopardizing her future, he selfishly responds that his will be at risk if they stay there.
- 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.
- Ripped from the Headlines: The Boston Americans are a thin mock-up of the real life New England Patriots football team based in Boston, who were involved in a controversial ball deflating scandal.
- 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. It’s nothing at all like The Departed.
- Surprisingly Realistic Outcome: At first Bart is all for Boston as he believes it appeals to his bad boy nature. Once he gets there he finds it’s not a criminal wasteland like in Black Mass where southie working class gangsters ruled the underworld with an iron fist. In the decades following those portrayal’s Boston has worked to reduce crime rates and better infrastructure and education, to prevent such criminality.
- 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.
- The neon sign at the hotel that family stays at reads, "Free NESN, no ESPN".note
- Two of the candlepin alleys the family visits are named "Yankees Suck" and "Lakers Suck!", respectively.
- 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.
