When Brian tells Stewie he is getting a bit old for a teddie, Stewie says, “Brian, I’m one!” when Brian responds with, “Still?” demonstrating that Stewie does not age through the series since he turned one year old in "Chitty Chitty Death Bang" in 1999.
This episode first appeared on the weekend of Winter X Games XI, which also took place in Aspen, Colorado, and featured different competitions of skiing.
When searching on the database for who took Rupert, it is shown that Stanford watches Cold Case Without a Trace, and Yu-Gi-Oh!.
Sharon Stone kills her lover after sex, as in the film Basic Instinct. She kills the man in the fashion of a praying mantis. The man was voiced by Connor Trinneer, better known as Commander Trip Tucker on Star Trek: Enterprise.
On the car’s DVD player, Peter watches an episode of the Nickelodeon cartoon SpongeBob SquarePants complete with an actual recording of “The Campfire Song Song” from “The Camping Episode”. The director of “Road to Rupert,” Dan Povenmire, wrote for Spongebob and in fact wrote the “Campfire Song Song.”
The James Taylor song that Brian sings when hitchhiking is called “Country Road”.
The song played during the montage of Meg driving Peter is "I'm into Something Good" by Herman's Hermits from 1964.
During the scene when Stewie is imagining Rupert's funeral, the rank insignia he is wearing denotes Captain. However, in the film Start Trek II: The Search for Spock, Kirk, who Stewie takes the position of, is actually a Rear Admiral.
Stewie says he bought the chattering teeth from Jack's Joke Shop in South Attleboro, Massachusetts, which was previously mentioned in “Lethal Weapons.” In the real world, Jack’s has been in Boston, Massachusetts for 50 years.
Stewie and Brian get a ride from Bandit from Smokey and the Bandit. The character Frog, portrayed by actress Sally Field in the film, is also in the car, causing Stewie to comment "Good luck tapping some of that hot, hot Sally Field tail" to which Bandit responds "I don't like it any more than you do"!!.
Brian can be seen selling a copy of Stewie Griffin: The Untold Story at the yard sale. In addition, the DVD version has Lois complaining about the DVD not being a movie, but instead three episodes back to back, calling it "an insult to the fans." She is then dragged away by FOX employees.
According to the DVD commentary, the writers of this episode tried for 'months' to get the 1980's 'Juicy Fruit' commercial into the episode, in which Brian and Stewie would snowboard the mountains while the song played in the background. The scene was later approved and put in Something, Something, Something, Dark Side in which Han/Peter snowboards instead of Stewie or Brian.