At a yard sale, Brian accidentally sells Rupert, Stewie's teddy bear, to a man who moves to Aspen shortly after. Stewie wants to get Rupert back, and Brian tags along. They take a helicopter to finally reach Aspen, where Stewie challenges the man to a skiing race to win back Rupert.

Meanwhile, Peter buys his old Evel Kinevel gloves at the yard sale and tries to do a stunt with the car, but crashes it, leading to his license being revoked. Meg becomes his chauffeur, much to his dismay, but after putting up with her father and his buddies acting like children, Meg releases her rage onto a man who calls her a "dumb bimbo", earning Peter's respect (at least until Peter gets his license back and starts treating her like crap again).