YMMV / The Trail to Oregon!

• And You Thought It Would Fail: Nick Lang revealed after the fact that lots of people in Team Starkid had low hopes for TTO, given that it was a highly slapdash production that had been through countless rewrites since Jeff Blim was in college and its script still wasn't fully set in stone right up to opening night, and that Ani has a much larger cast because most people who were given the option thought that Ani would obviously be the more successful show. In hindsight, the tiny cast and the loosey-goosey improvisational feel of TTO made it one of Starkid's most popular shows ever, and the fact that TTO was so much fun to do is a major reason it's the only Starkid show that's been remounted off-Broadway after its original run.
• Big-Lipped Alligator Moment: Arguably "Dysentery World" and the scene with Cornwallis, which whilst plot relevant, makes little sense and comes right out of the blue.
  • A minor example occurred in one production when Joey forgot his lines during Independence and instead improvised with "ho ho ho" sounds instead until he picked the song up again by shouting "ox like me!". This was later lampshaded in a blooper compilation in which Joey described the blooper, noting how his exclamation didn't make any sense. It's now reached Memetic Mutation levels where Starkid fans will interject the phrase "ox like me" into online threads and then continue as though nothing happened.
  • There's also the song "Caulk Your Wagon", which regularly wins "Worst Song" rankings in the fandom, not because it's musically bad or even that it doesn't make sense in the plot but that it doesn't make sense that of caulking the wagon should be a whole song, where it's not even clear what the actual joke is, other than "caulk the wagon" being Inherently Funny Words. (It vaguely seems to be riffing on Paint Your Wagon and on incongruously cheery musical numbers from old-timey musicals in general.) Some licensed productions just drop this song completely (one of them replacing it with a simple one-liner Double Entendre about the "size of McDoon's caulk" that structurally serves the same purpose.)
• Crossover Ship: There are some who ship the Daughter with the Princess from Twisted: The Untold Story of a Royal Vizier.
• Ensemble Dark Horse: Grandpa. Audience members commented you don't really get a sense of how great Corey Dorris' voice is unless you vote for the Grandpa Dies ending.
• Fridge Brilliance: The Running Gag about the Father blaming "God" for his own screwups makes sense when you realize that, as referenced in the opening number, the Father is played by the writer of the show.
  • One of the citizens in "Independence" warns the family that his whole family died of dysentery and "you will too unless you stop to rest frequently". Sure enough, when does one member of the family inevitably catch dysentery? Right after the Mother makes them do a speed run to catch up to McDoon. (The Daughter wasn't with them, but, then again, her dysentery turns out to be faked.)
  • Crosses over with Fridge Horror: The Ox's bizarre deformities (including, notably, having a human hand) make a lot more sense when you hear the General Store Guy make a Suspiciously Specific Denial about there being nothing "unnatural" about the love between himself and his own ox. The deformed ox he's trying to get rid of is his own Half-Human Hybrid son.
  • The show used Reality Subtext when announcing the date the family embarks on their trip to Oregon — it was always the actual date of the performance, minus 166 years (from 2014 to 1848). The thing is, the show ran from July to August — and the original Oregon Trail game will outright tell you that if you leave too late in the summer, there's a good chance you won't make it to Oregon before disastrously running into winter, which is exactly what happens in the show. (In fact, in the original game July is the latest you can leave and August is too late to start your journey.)
• Fridge Horror: Averted. The daughter certainly wasn't raped by McDoon—she was his kidnapped child bride, but he made a point of not touching her until they were "properly married."
• Hilarious in Hindsight: For fans of Twisted: The Untold Story of a Royal Vizier. The Princess has gone and married Aladdin, and he's turned out to be as much of a useless Lazy Bum as Ja'far warned her he'd be. (It's even established that she got pregnant at the age of 17.) That would mean Grandpa IS Ja'far, albeit a version of him rendered unrecognizable by senility. He definitely still hates Aladdin though.
  • For fans of Firebringer, the fact that Lauren Lopez, who plays the Firebringer, plays the titular wagon fire in "Wagon on Fire".
  • The Self-Deprecation in the line "We're Broadway-bound in Ore-gound/'Cause there's no Broadway in Chicago!" is extra hilarious — and satisfying — with the success of this show making it the only Starkid production to get a second run in New York (off-Broadway, but still impressive as hell for a goofy Oregon Trail parody).
• Jerkass Woobie: Cletus Jones. He may be a criminal, but he genuinely loves McDoon, who views their relationship as Situational Sexuality. You gotta feel sorry for a guy in that situation.
• Memetic Mutation: God is a vicious, two-faced prick!
• Superfluous Solo: "Naked In A Lake" as a random payoff for the Running Gag about the Son's skinny-dipping obsession seems to mostly exist because otherwise Lauren Lopez wouldn't have any solos in the show (unless the Son gets chosen to die, which in fact happened fairly often).
• Suspiciously Similar Song: Many have remarked on how "Lost Without You" sounds like a reworked version of "Granger Danger".
• Tear Jerker:
  Mother: I'm going to take what family I have left, and we are going to find our own way to Oregon. And you... just enjoy the rest of your vacation.