The Marshes, Broflovskis, Cartmans, and the Stotches planning a family vacation skiing at Aspen. They express concern over the cost of the trip, until Chris and Linda point out that, in exchange for attending a half-hour timeshare meeting, they get a free two-day trip there. The parents then make up their minds to go that weekend, and they take their children with them. They drive in the next night seeing the town of Aspen.
On their first day in Aspen, they awake to find two timeshare salesmen, named Phil and Josh, waiting at the door. They urge them to attend the meeting, but the parents are a little reluctant, as they had hoped to attend it later, and ski right at the moment. In the boys' room, Cartman gives Butters a "Hitler" while he's sleeping. He describes it as "Putting your finger up your butt, then wiping on the person's upper lip and giving them a little Hitler mustache". Butters can smell the crap, and Cartman says, "That's why they call it Asspen!"
They next are at the bunny slope, and an instructor, called "Thumper", is teaching them the two primary feet positions in skiing: the pizza, (skis wedged together in an angle) and the French fries (skis are parallel). When Ike attempts to ski down the slope he crashes through the wall of the lodge. During the boy's practice, a teenage skier and stereotypical arrogant bully, named Tad Mikowski, comes by and starts to tease Stan because of his surname, saying that rather than "Stan Marsh", he ought to be called "Stan Darsh". After this moment, the main plot of the story parodies classic teen and sports films from the 1980s; the only difference is that the other boys show no concern whatsoever, however none of the other parties involved seem to realize this. Through the timeshare presentation, as it has been three hours instead of thirty minutes. The salesmen are having no progress in persuading the adults to rent any of the condominiums there. At last, Randy and Gerald tell the men that the whole group is now leaving. Phil and Josh seem to go along with this decision, and merely ask for the adults to turn over their table place cards. They agree to do so. As it happens, these place cards have the "red sticker" on them; which can be redeemed for one of three prizes. The parents, not wanting to waste anymore time, refuse, and the salesmen start crying. The parents then agree, in tired tones, to claim their prize. It is an exclusive ski lift. They are relieved that they can finally go skiing, and climb aboard. To their horror, however, the lift simply carries them right back to the meeting room.
The boys are still practicing skiing, until Tad comes by again. Now he has with him Stan's supposed older girlfriend, Heather (whom he's never even met before), who he is now dating. Tad then challenges Stan to a little skiing race, despite Stan being only a beginner, a little boy and even admits he couldn't beat Tad. On the condition that Tad will leave him alone if he wins, Stan accepts the challenge. Stan loses the race, however, (but he had predicted that that would happen). Then in true 80's movie fashion, a dorky-looking yet somehow hot redheaded teenage girl approaches him and says that he was really brave. She then invites him to dance at the teen youth center. That evening, at the youth center, the boys discover that Tad's very wealthy, businessman father plans to bulldoze the Youth Center, though Stan once again expresses no concern.
Whilst at the center, Tad goes on stage, and sings a very poorly written and performed song about Stan. Afterwards, Stan is very irritated by the terrible song, and Tad foolishly mistakes Stan's annoyance to be a request for a rematch. The rest of the teens want to keep the youth center, and they make a condition on this new competition: If Tad wins, his father can bulldoze the youth center down. If Stan wins, however, the youth center stays, and so,Tad agrees, strongly hoping he will win. He then arranges for the race to be held on the K-13, which is considered "the most dangerous run in America". Kyle tries to talk Stan out of it; he's already lost one friend (Kenny), and he doesn't want to lose another (especially his best friend). Stan coldly replies that this isn't about what Kyle wants. Even when the mysterious, old mechanic from "Butters' Very Own Episode" tells Stan about the horrifying history of the mountain, which involved the tales of thirty-five people who have died gruesome deaths whilst going down it,and how a group of students were brutally murdered by a psychotic wolf boy who had escaped from a mental asylum. It is also the burial ground to be a tribe of Vampire Witchicaw Indians who ate the flesh of children with no eyes. Stan is still determined to attend this race.
For some reason, Stan automatically considers it important to beat Tad from this point onward. He asks the trainer, Thumper, for special training, and he agrees, although in a rare moment of competency for the show he doesn't think he can do it. Even the redheaded teen pitches in, and instructs Stan, accompanied to the ideal song "Montage". In the scene, Stan trains and studies, the parents are forced to sit through their timeshare meeting and a tearful Kyle stares at the K-13 holding a picture of himself and Stan, while Cartman is seen giving Butters the "Hitler" in his sleep again, and the song ends where Stan has finally completed his training.
Even the next day, the parents are still trapped at the timeshare meeting, and, unable to bear it any longer, they look to the police for help. They get no support from them as they reveal that they are controlled by the time sharing company. However, the parents are all forced at gunpoint by the officers, so they will agree to rent some condos after all.
When the big race begins, Tad has an advantage over Stan, despite Stan's heavy training he is still no match for Tad's several years of skiing. He still sneakily stops along the way now and then in a cowardly style, attempts to sabotage Stan's efforts, for example by chopping down a tree to block him, and pouring down a bucket of salt to make him slip. Although, Stan is moving very gradually,he successfully manages to go around all of the obstacles. The redheaded teen really wants Stan to win, so the youth center will survive, so she distracts Tad by lifting up her shirt and showing him her breasts. Stan makes it through the finish line first, and the youth center is saved. Kyle is relieved that Stan survived the slope, and Tad finally gets his much deserved comeuppance, as he is very embarrassed that he has lost to a much younger person, and loses his arrogant persona and confidence.
Ironically and quite humorously, if Tad had merely run the course without trying to sabotage Stan, he would have won the race by a large margin just like the first time. Heather then comes over to Stan and says she wishes to be his girlfriend "again" (despite Stan has never met her before, and the fact that she is considerably older than Stan). The redhead is a little put out by this, as she has a crush on Stan (She is also much older than Stan is, like Heather). She tries to be a good sport, though, and encourages Stan to accept Heather's offer.
The tension ultimately builds upon whether Stan will accept, or choose the redheaded girl, but at that moment, the parents are finally freed after having rented some property. They then ask the boys how they enjoyed skiing, to which they respond that they hated it, and are upset that now they'll have to come every year. They then leave to return home to South Park. As the episode ends, the redheaded girl reveals to Thumper what's really under her shirt: Instead of breasts, she has two Kuatos from the movie Total Recall, says the line, "Quaid.......start the reactor."