After Homer refuses to pay an airport tax, the Simpsons must hop a train to get to their Delaware vacation destination. A hobo on the train entertains them by telling stories, all of which are similar to classic tales, but the hobo’s versions are twisted, and star Simpsons characters. The first story is about Paul Bunyan, who in this tale is a giant Homer. Giant Paul/Homer crushes houses as he walks, and washes townsfolk away in his spit when he drools. Sick of having to feed Paul, the townsfolk get him drunk and drag him out of town, then banish him. Paul carves himself an ox, which comes to life and becomes Paul’s friend. But Paul wants a different kind of friend. He spots Marge in the distance, and is smitten, even though she’s small enough for him to use as a Q-tip (which he does). Marge is just as fond of Paul, though given his size she’s hesitant to get fully intimate. The townspeople spot a deadly meteor headed for them, and realize Paul is the only one big enough to save them. Paul agrees to save them by batting the meteor from its path as if it were a giant baseball, but he bends down for a good-luck kiss from Marge at just the wrong moment, and the meteor goes down his pants. Paul grabs the meteor and throws it over the horizon. It lands in Chicago, causing the Great Chicago Fire. The hobo agrees to tell more stories if someone will give him a sponge bath.

After Homer finishes giving the hobo a sponge bath, the hobo tells the story of Connie Appleseed. Connie is Lisa, a member of the Simpsons/Appleseed family heading west as part of a wagon train. Homer accidentally shoots a buffalo from his covered wagon,and “Connie ”is horrified. Homer is delighted to have buffalo to eat, and shoots another one. Everyone in the wagon train starts to shoot buffalo, but Connie warns them they’re going to kill the whole species. Trying to think of an alternative food, Connie suggests apples, but the wagon train wants no part of the apples. Connie refuses to stay with the “wagon train of death,” and goes her separate way, planting apple trees everywhere. Soon, the wagon train settlers kill all the buffalo, and begin to starve. Desperate, they prepare to eat each other, but Connie appears, bearing apples,and saves the day.

Then the hobo tells the story of Tom Sawyer and Huck Finn, with Bart as Tom and Nelson as Huck. Tom and Huck are whitewashing a fence when Becky Thatcher (Lisa) happens along. Huck shows off by walking across the fence on his hands, to impress Becky. But the fence collapses, and Huck crashes. Becky hurries to his side, and they’re holding hands when Judge Thatcher (Homer) sees them. The Judge insists that Huck and Becky must now get married. But at the shotgun wedding, the creature in the top hat, about to marry Becky, turns out to be a pig. Huck and Tom are high-tailing it out of town, with Judge Thatcher and other townspeople in pursuit. Huck and Tom jump on a raft, and escape down the river, but Judge Thatcher and his men chase Huck and Tom to tar and feather them. The boys paddle desperately but lose ground. They climb onto a steamboat to hide,and fall onto the paddle wheel, which catapults them into the steamboat saloon. A gunfight breaks out in the saloon, and Moe tosses Huck and Tom overboard. They sink to the bottom of the river…where Judge Thatcher and Sheriff Wiggum are waiting. Huck and Tom are taken back to town and hanged, next to Becky (hung for marrying a pig), the pig (punished for marrying Becky), and Milhouse (because nobody likes him). The five of them swing back and forth on a rope, like an executive desk clacker, which, the hobo explained,is how those desk-toys were invented. With that, the train arrives in Delaware, and the Simpsons get off.