Road to Rupert is episode 09 of family guy season 05. It was originally aired on January 28, 2007.
When the family has a garage sale, Brian accidentally sells Stewie’s beloved teddy bear Rupert. Stewie is so distraught that Brian takes him on a cross-country road trip to Aspen, CO. When they find the culprit, Stanford, Stewie challenges him to a ski-off to get Rupert back. Meanwhile, Peter loses his license, so Meg has to drive him around.