- Blooper: The high level of Improv, Audience Participation and Joey Richter's Loads and Loads of Roles created many opportunities for these, some of which were posted on the YouTube channel. (This is even lampshaded in "Gone to Oregon", with the lyrics asking "Who will forget their name?/And who will get the YouTube fame?") Notable ones include:
- Joey multiple times simply forgetting a whole stanza of the Patter Song "Independence" and either replacing it with "ho-ho-ho-ho" or just dancing in awkward silence.
- Corey Dorris' beard coming off during "Sometimes It Pays to be an Animal" leading to him frantically trying to get it back on begging the kids "Don't tell nobody!" and Jaime Lyn Beatty commenting, "There sure are a lot of dark secrets in this family!"
- Jeff Blim forgetting to wear his long underwear under his clothes in one show, leading to him almost actually stripping onstage during "Naked In A Lake".
- During the marathon shoot of all the possible Multiple Endings for the YouTube version of the show — which were still in front of a live audience — at one point Joey Richter came back onstage as the Doctor instead of the Ox during the intro to "Naked in a Lake", prompting him to exclaim "I didn't know we were going to the end!"
- An intentional prank, where instead of Rachael Soglin as the Mother seductively approaching the Father giving her final line of the play, "Come on, honey, the water's just right" the Ox does it, causing Jeff Blim to actually recoil in horror.
- A minor but somehow hilarious one in the YouTube version of the show, where McDoon flings a bucket offstage at the end of "Caulk Your Wagon" and it apparently accidentally rolls down a set of stairs, audibly, for an uncomfortably long time. Prompts him to casually remark, "Didn't know there was a ridge there".
- The Cast Showoff: Jeff Blim, who cowrote the show, gives himself an opportunity to come out during the finale number, "Naked in a Lake", to perform a saxophone solo.
- Dawson Casting: Obviously, for the Daughter and the Son, with all the actors being around the same age in Real Life. Interestingly, Playing Gertrude is averted for the Mother — Rachael Soglin seems young for someone who has a teenage daughter, until we find out the Daughter was a Teen Pregnancy.
- Dueling Shows: This show came a year after a production titled Oregon Trail: The Play by the NOLA Project in New Orleans, with extremely similar structure and themes (although the latter veers much more into What Do You Mean, It's Not Political?). Thanks to Team Starkid's existing fanbase and tradition of putting their shows on YouTube, The Trail to Oregon pretty much "won" this duel in terms of name recognition, though both shows have seen their fair share of regional productions.
- No Budget: A prime example of success through adversity, this is one of Starkid's most successful shows despite having extremely conspicuous limitations on their costume and prop budget and having a cast of only six, being the lower-budget sister show to Ani. (The Langs have remarked on how this is actually a greater constraint than they had in college during the A Very Potter Musical days, when the one thing they could get for little money was large casts of actors willing to work for fun and exposure.) Many of the things about the show that are most beloved come from the low budget, like the sight gag of the Bandit King's "horse", the DIY sound effects made by Joey Richter's mouth sounds, or just the fact that Joey Richter plays "Everyone Else". As a bonus, these factors have made the show easy to license out to other theatre companies, greatly extending the longevity of the show's brand.
- Reality Subtext: The family is originally from Illinois, the same state in which the show was produced (in Chicago). In the original run, the date the Father gave at the beginning of the show was the actual month and day at the time, transferred to 1848. (It helped that this run was through July and August, within the range of dates the game gave you as a possible time to set off on the trail.)
- Sleeper Hit: When the decision was made to do this show and Ani as sister repertory productions in Starkid's 2014 season it seemed like the parody of Star Wars was a far more likely hit than the parody of Oregon Trail, especially with the latter being a shorter, fluffier, Denser and Wackier show with intentionally very bare-bones set design and costumes. Contrary to those expectations, it's this show that ended up being the big phenomenon, with local productions as far away as the Edinburgh Fringe Festival, and Ani that got remembered as a relative disappointment.
- Jeff Blim later revealed that he'd been working on the script for this show for over ten years before it was finally made as a Starkid production, including having it rejected twice from the New York Musical Theatre Festival. (Although the older versions of the show were very, very different from what eventually got made — see What Could Have Been.)
- What Could Have Been: The "Unsung Starkid" show in 2014 performing Cut Songs from Starkid's back catalogue revealed that The Trail to Oregon went through huge changes throughout its ten-year existence as Jeff Blim's pet project before finally being produced. The show was originally — if you can believe it — Denser and Wackier than the finished show, with most of its earlier iterations involving an actual Time Travel The Game Come to Life plot, where children from the present day getting transported back to the actual Oregon Trail via playing the game at school. It turns out that the Father being named "Jack Bauer" in the recorded performance of the show was a sly reference to the fact that Jack Bauer from 24 was a major character (thanks to one of the kids entering his name into the computer and causing him to come to life).
Trivia / The Trail to Oregon!