After the Simpsons win a trip to Delaware, Homer refuses to pay a $5 airport tax for his flight. After Homer violates the Anti-Fist Shaking Law, the family jumps onto a freight train where they meet a singing hobo who tells them three stories.
Homer portrays Paul Bunyan, a great burden on the local townspeople, as he crushes their houses and greedily eats all their food. Eventually, the townspeople drug him and drag him out of their town. Out of loneliness, Bunyan carves a block of stone from the mountains into a blue ox that he calls Babe, who is rendered alive by an electric shock. In his travels with Babe, Homer creates several landmarks. Bunyan later meets a young woman, (played by Marge) and though she is initially frightened of him, the two fall in love. When a meteor is soon to hit the town, the townspeople call Paul back to help them. Paul obliges and throws the meteor towards Chicago, starting the Great Fire there, but not before it hits him in the backside.
After the hobo has told this story, he asks them for a sponge bath as compensation. Disgusted, Homer is forced to oblige, as nobody else will do so, but the hobo does not mind anyone seeing his nakedness.
The hobo's second tall tale revolves around Lisa as Connie. Connie is part of a wagon train, and all of the travelers shoot and eat buffalo. Connie, who is against the practice, states "If you don't stop this slaughter, you'll wipe out the buffalo." After which they all ridicule her she is worried that no one is eating a renewable source of food and finds some apples for the pioneers to eat, but they reject them. Eventually, she changes her last name to "Appleseed", and leaves her family to journey across the United States and plant apple seeds wherever she goes. Meanwhile, the Simpsons change their surname to "Bufflekill" and they succeed in killing all the buffalo in the land. The travelers eventually starve, and just as they are about to cannibalize Homer, Connie returns and offers them apples instead.
The hobo's third tale tells the story of Tom Sawyer, whom Bart portrays, and Huckleberry Finn, whom Nelson portrays. Tom is a rebellious trouble maker while Huck is a bully. Huck is caught holding hands with Becky (Lisa) and is forced to marry her by her father (Homer). Huck dodges the marriage and goes on the run with Tom, leaving Missouri for Missoura. However, they are chased by townspeople led by Becky's father and their families. Huck and Tom flee to a river boat, but are thrown into the Mississippi River and are caught by the townspeople. At their funeral, Tom and Huck are first revealed to not be in their caskets, seemingly watching the proceedings from the rafters which they have big smiles on their faces, until Reverend Lovejoy orders their bodies lowered into the caskets, revealing that Tom and Huck are in fact dead.
The family arrives in Delaware and disembarks the train, but the hobo reminds them that they owe him one more sponge bath as compensation. Homer promises to catch up with them in an hour and volunteers to stay behind to do the dirty work.