Original Airdate: May 20, 2001

The family rides the rails to travel to Delaware, and while on the train, a hobo tells them some famous tall tales, casting them and other ''Simpsons'' characters into the stories.

* CallBack: The family's lines at the beginning ("The Simpsons are going to Delaware") were taken from the end of "Behind the Laughter" where Homer edits together the next new episode of the show.
* FanDisservice: The Hobo's requested compensation after each story was getting a sponge bath by Homer.
* TheStinger: Homer's line "Oh boy, buffalo testicles!" is heard over the Gracie Films {{vanity plate}}.

!!!''Paul Bunyan''
* AllOfTheOtherReindeer: The townspeople drag Paul out of town for always clumsily crushing everything, but then need him to save them from an oncoming meteor.
-->'''Paul:''' When I'm crushing and killing you, you hate me. But suddenly, when I can save your life, I'm Mr. Popular?
-->'''Lenny:''' Yep, that's pretty much it.
-->'''Paul:''' Woo-hoo! I'm Mr. Popular!
* AnachronismStew: While taking place in the 19th century, Paul and Babe are seen fighting Film/{{Rodan}} in a modern metropolis. Lisa points this out.
* HistoricalInJoke: The Chicago Fire of 1871 was started by Paul throwing the flaming asteroid from his pants.
* INeedADrink: When asked by her husband how birthing a baby the size of a small building was, all Mrs Bunyan can do is ask for whiskey.
* RumpRoast: Paul gets a flaming asteroid down his pants.
* ScreamingBirth: Hilariously (and horrifically) implied. When Paul's (normal-sized) father see's his giant son, he asks his wife how she took it. All she can mutter is "Whiskey...please".
* SlippingAMickey: Paul drinks one carriage full of beer and instantly gets knocked out cold. Moe reveals that he slipped a couple of giant pills into the beer, then remarks he's [[CrossesTheLineTwice off to the barn dance]] while carrying a pill.

!!!''Connie Appleseed''
* GenderFlip: The ''Johnny Appleseed'' legend is changed to a female to fit animal-lover Lisa into the story.
* MyGodWhatHaveIDone: Connie's father says this when he realizes that he's been shooting the buffalo to extinction. When his son says there are two more left, he shoots them both and repeats the line.

!!!''Tom and Huck''
* BaitAndSwitch: During Tom and Huck's funeral, the camera pans upward to the two looking down from wooden beams, implying they survived. It turns out the townspeople stuffed their corpses and are being lowered into their caskets.
* DownerEnding
* LongList:
--> '''Nelson''': We got any food left?\\
'''Bart''': Hmm. Looks like we're out of corn pone, fatback, hardtack, fat pone, corntack.\\
'''Nelson''': Any "tackback"?\\
'''Bart''': "Tackback"?\\
'''Nelson''': I mean "backtack".\\
'''Bart''': Plumb out.
* ShotgunWedding: Becky's father does this to Tom for holding hands with Becky. He also remarks how he and his wife got together via this method, with a hilarious GenderFlip version of it being ''Homer's'' father who forced Marge to marry his son at gunpoint, and is ''still'' behind her with the shotgun. When Marge remarks that they've been married for 10 years and that Grampa can put the gun down now, he relents... and Marge immediatly bolts out the door.
--> '''Grampa''': DANGIT ALL!!
* ShoutOut: Dr. Hibbert is seen singing [[Theatre/ShowBoat "Ol' Man River"]].
* WholePlotReference: ''TomSawyer''.