Stewie and Brian travel back in time to 17th-century Jamestown and make too many close calls with changing history. Stewie decides to destroy his time machine, but comes to regret it when Brian dies after being hit by a car. Devastated by his death, the Griffin family goes out and adopts another dog from the pet store, Vinnie, who is quickly accepted by all the members of the Griffin family, other than Stewie, who can't get over the loss of Brian.

When Peter and Quagmire discover that their singing voices create beautiful harmony together, they form a singing/songwriting team, in the vein of Simon and Garfunkel. However, tensions run high when fame gets to Peter’s head.

When Carter Pewterschmidt cancels the annual Quahog Christmas carnival, because he hates the holiday, Peter must transform his father-in-law from a Scrooge into a hometown hero in order to salvage the event. Meanwhile, Stewie devises a master plan to get the one and only thing he wants for Christmas.

Stewie and Brian form a band aimed at children, but face a breakup when they set their eyes on the same girl. Meanwhile, Chris gets a job as Quagmire's personal assistant for his sex life.