The Town/References

Cultural references

 * The title of the episode is a reference to the movie , which also takes place in Boston.
 * Homer references the Aerosmith, and Ben and.
 * Marge references .
 * There is an online parody called "The Real Housewives of South Boston" using the very Southies that Bart wishes to hang out with.
 * Bart references  and its theme song is sung by the kids in detention and it is later played during the end credits.
 * The song by  plays when Bart and Homer are candlepin bowling.
 * Boston Americans is a reference to the former name of the baseball team.
 * The handsome quarterback is a parody of, the coach is a parody of , Bonkowski is a parody of , the mascot is a parody of , and the scandals are parodies of headsets and respectively.
 * They're also a parody of.
 * Bart (wearing a blue cap) being intimidated by Apu and Sideshow Mel (wearing red clothes) is a reference to the rivalry between the gangs (identified by their blue clothing) and  (identified by their red clothing).
 * The Duck family from  are seen when the Simpsons walk by Charles River.
 * The Cheers (which takes place in Boston) theme is heard a couple of times during the episode.
 * At the Massachusetts Institute of Technology, nerds are seen playing and with s.
 * Bobbleheads of Aimee Mann, and Bell Biv DeVoe attack Homer.
 * The Bill "Spaceman" Lee Planetarium is a reference to pitcher.
 * Cumbies is slang for, a regional chain of convenience stores based in Framingham, Massachusetts.
 * Dukakis Eyebrows sells eyebrows in the style of Michael Dukakis.
 * Filene's Basement's Attic is a reference to, a chain of department stores.
 * Lechmere's was a real retail store chain.
 * Nekco is a reference to, the New England Confectionery Company.
 * Noam Chomp-Sky's Grinders and Frappes is a reference to Noam Chomsky.
 * Robert's Parish is a reference to former basketball player Robert Parish. The stain glass window features an image of him.
 * Spenser: For Hire's Gifts is a reference to the TV series .
 * The statue of Paul Revere is seen.
 * People appearing in the crowd scene at the Boston Americans parade:
 * The cast of Cheers (Cliff Clavin, Carla Tortelli and Norm Peterson).
 * Noam Chomsky.
 * Michael Dukakis.
 * Carlton Fisk.
 * Marvelous Marvin Hagler.
 * Ally McBeal from .
 * The Mighty Mighty Bosstones.
 * New Kids on the Block.
 * Bobby Orr.
 * and Mark Wahlberg, referencing , which takes place in Boston.
 * of Aerosmith.
 * Elizabeth Warren.
 * Cameron and Tyler Winklevoss.
 * Bart's comment about Boston Americans' victory parades being a state holiday has a minor ring of truth to it: from 2001 through the episode's original airing in 2016 there have been nine sports victory parades in the city. Four for the Patriots, three for the Red Sox, and one each for the and, and one commentator on the morning show for local radio station  stated that children were beginning to erroneously believe that victory parades were an annual event.
 * Two jokes, as the Celtics are the city's most victorious sports team with 17 championships as of the episode's original 2016 airing, are shown:
 * a Statue of Liberty-style statue of Larry Bird in Boston Harbor.
 * Bart walks past a church called "St. Robert's Parish" where Robert Parish is both the pastor and depicted on a stained glass window.
 * In the February 12th re-airing of the episode, a new hidden reference to the Patriots' win was added. This scene replaced the Springfield/Boston score with the Patriots/Falcons Super Bowl score.
 * Bart walks past a church called "St. Robert's Parish" where Robert Parish is both the pastor and depicted on a stained glass window.
 * In the February 12th re-airing of the episode, a new hidden reference to the Patriots' win was added. This scene replaced the Springfield/Boston score with the Patriots/Falcons Super Bowl score.

Massachusetts area references

 * Mass. Ave is a reference to the and it spoofs ' too with characters resembling ' cast members,  and  talking about robbing The Harvard COOP bookstore and drinking "Fribbels" beforehand.
 * -esque stickers adorn the wall of the tunnel and the neighborhood Lisa and Bart walk through.
 * " & Motel", complete with a poster for area UHF TV station 's The Movie Loft in their room.
 * This sign also mentions NESN, which is the, as opposed to Connecticut-based , and is the regional sports channel based out of the Boston Area.
 * The town of Quimby is a parody of.
 * The Duncan Doughnut's cup thrown at the Simpson's car is a parody of, with appearing at the parade.
 * Stores and kiosks at include:
 * "'s Attic" (specifically in the same location as the real-life Ned Devine's Irish Pub).
 * "Lawful Seafoods", a parody of.
 * "'s Gifts" kiosk complete with the character of Hawk running it.
 * The Red Auerbach statue.
 * "Menino's Paninos" kiosk.
 * The "Do your job, Homer" line the Handsome Quarterback says in Homer's hallucination was a motto/tagline the Patriots used during their runup to Super Bowl XLIX. Further, the Handsome Quarter back is voiced by Michael Chiklis, who introduced the Patriots for Super Bowl XXXIX.
 * "'s" was a precursor.
 * "Cumbie's" is a regional convenience store chain throughout eastern Massachusetts, New Hampshire, Rhode Island, and eastern Connecticut.
 * "104 BCN" was an area radio station that Billy West used to work for as an on-air personality.

Trivia

 * The tunnel scene was slightly edited from the version on the trailer:
 * Homer's line went from "Delicious, delicious rage." to "I've never loved hating anything so much!"
 * Smog was added to the background.
 * This episode ended up airing on the Pacific Coast at 9:12pm PT due to overtime of the 2nd, and other lead-out programs airing first.

Goofs

 * Inside the tunnel, a blue truck is behind the Simpsons family's wagon, after the townie throws a cup at them, there's a car instead.
 * The Boston Americans' mascot had no helmet, meaning that he wouldn't be allowed to participate in the play even if he is one of the players.
 * Homer apparently first learns of candlepin bowling in this episode, despite previously making reference to it in My Mother the Carjacker.