When Lenny wins the lottery and invites the Simpson family to a celebratory party at a posh hotel, Bart meets his doppelganger, Simon Woosterfield, who happens to be a member of the richest family in Springfield. Simon and Bart decide to switch places, and Bart arrives at the lavish Woosterfield mansion only to find football great Joe Montana (guest-voicing as himself) hanging around the estate. As Simon adjusts to the simple life over at the Simpson household, Bart begins to notice his wealthy new siblings acting strangely toward him. With some frightening words of wisdom from Mr. Burns, Bart realizes his new siblings are plotting his demise so they can inherit the Woosterfield family fortune all for themselves. Lisa and Simon must reach Bart before he goes from riches to ditches. Blackboard: 'There's no such month as Rocktober'.

When the Simpson family takes a road trip to a cabin in the woods, a series of flashbacks depict Homer and Marge's blissful courtship and their early married years. They recall their first encounter with Flanders and Maude twenty years prior at the very same cabins, where Flanders insisted the unmarried Homer and Marge stay in separates rooms. Later, they recall when they each met distracting members of the opposite sex who nearly wooed Homer and Marge away from each other. Bart and Lisa also reflect on happier times from their early childhood. Despite the obstacles and the passing of time, Homer and Marge attempt to see the forest for the trees.