The episode begins at Meh Burger, where Sonic cheers Knuckles on as Knuckles chugs down a milkshake. Knuckles cheers, then gets brain freeze. Just then, Tails runs in and tells Sonic and Knuckles that their band, Dude-itude, has been asked to play a concert on the other side of Bygone Island. Sonic forgets that he, Tails, and Knuckles were in a band, so Tails reminds them of the time they saved all the women from Justin Beaver's hypnotic music. Sonic and Knuckles are still confused, so Tails tells them there were crackers in the green room, which suddenly refreshes their memories. Sonic asks Tails how they and Knuckles will get their gear to the concert, and Tails reveals the Dude-Mobile to them. Knuckles is excited about the road trip he, Sonic, and Tails are about to take.
As Sonic, Tails, and Knuckles pack the Dude-Mobile, Amy tells them to have fun on their trip, and not to do anything she wouldn't do. Sonic then tells Amy that he thought she told him to have fun, irritating Amy.
The Dude-Mobile sets off, and Sonic tells Tails and Knuckles that since they'll be spending the next fifteen hours in it, they should make some productive use of their time. He then puts in a tape cassette featuring one of their songs, and they sing along to it. After their song, Sonic is determined that nothing can stop them now. Knuckles, who now has to use the bathroom, tells Sonic and Tails that he needs to stop now. Tails stops the Dude-mobile at a nearby restroom, and as Knuckles uses it, Tails looks over the map and tells Sonic that their route passes right by the famous water tower shaped like a ketchup bottle. Sonic tells Tails that he's never heard of it, and Tails tells him it was prominently featured in a deleted scene from Mutant Commando 3, and Sonic reluctantly agrees that they can make one stop.
Sonic, Tails, and Knuckles stop at the ketchup bottle-shaped water tower, which Tails takes pictures of, much to Sonic's disdain. When they get back on the road, Knuckles falls asleep, then wakes up, having to need to use the bathroom again. After they stop at the next restroom, Tails points out a sign leading to four cars leaning up against each other. Knuckles is excited to see them, but Sonic isn't. As Tails takes a picture of Knuckles leaning up against the cars, Knuckles accidentally knocks them over like a stack of dominoes, and he and Tails whistle nervously as they walk away from them. Sonic, Tails, and Knuckles then stop at a gift shop, and as Tails and Knuckles decide on what postcards to buy, Sonic waits impatiently for them.
A little later, Sonic, Tails, and Knuckles go to the home of the World's Largest Non-Rocking Chair, which the Old Monkey shows them. Knuckles asks the Old Monkey if he can sit in it, but the Old Monkey tells him that the chair is only to look at, not to sit in. An unamused Sonic then turns on his communicator to talk to Amy and Sticks. He asks them if they're as miserable as he is, but Amy tells him that she and Sticks are having a relaxing spa weekend. She then tells Sonic that she's sure his trip isn't as bad as he lets on, and the Old Monkey proves her wrong by showing Sonic, Tails, and Knuckles the cease and desist from the book of records he was sent. Amy then tells Sonic, Tails, and Knuckles to have fun and take lots of pictures, but the Old Monkey hears this and tells them not to take any pictures, much to Sonic's disdain. Knuckles then tells Sonic and Tails that he bought a scaled-down replica of the World's Largest Non-Rocking Chair at the gift shop (which is just a regular chair). Sonic facepalms himself while Tails takes a picture of the chair.
When Sonic, Tails, and Knuckles get back on the road, Knuckles has fallen asleep. An impatient Sonic then notices Mrs. Vandersnout travelling past them on her motor scooter, and a 60-Mile-Per-Hour Speed Limit sign. With Tails driving, they're only going 20 miles per hour, and Sonic snaps. He tells Tails to let him drive, and the two fight over the wheel, causing the Dude-Mobile to swerve. Sonic then takes control of the Dude-Mobile and tells Tails and Knuckles that they're going straight to their concert without stopping for anything. Just then, they get pulled over by a police officer. Tails tells the Police Officer about the Dude-itude concert they're on their way to, but the Police Officer isn't familiar with their band, and thinks that they're a bunch of delinquents. As Sonic tries to tell the Police Officer who he is, the Police Officer gives him a speeding ticket, and tells him, Tails, and Knuckles that he'll be keeping an eye on them. Sonic is distraught over getting another speeding ticket, and tells Tails and Knuckles that if he tried to fight it in court, they wouldn't accept "Gotta Go Fast" as a medical condition. He then tells Knuckles to take the wheel for a while.
Later, Sonic and Tails have fallen asleep as Knuckles drives the Dude-mobile. Knuckles comes to two paths near a tree, and asks the universe which way he should go. A bolt of lightning points to the left side, and Knuckles decides to take that path.
When Sonic awakens, he is shocked to find himself in the middle of nowhere, and a large, snaggle-toothed opossum in a trenchcoat sitting next to him. This awakens Tails, who is also shocked to see the Opossum, and causes Knuckles to swerve. Sonic asks Knuckles why the Opossum is sitting next to him, and Knuckles tells him that since he and Tails were asleep, he needed company, and the Opossum also looked like he needed company. Tails asks the opossum what he's doing in the middle of nowhere, and the Opossum tells him, "Biding my time.". Just then, a radio broadcast comes on, informing listeners of the Bike Chain Bandit, a criminal who escaped from prison. The broadcast describes the Bike Chain Bandit as a large, snaggle-toothed opossum wearing a trenchcoat and carrying a duffle bag filled with bicycle chains. Sonic realizes that the opossum sitting next to him matches that exact description. Sonic asks Tails and Knuckles if he could talk to him, then assures the Bike Chain Bandit that they're not talking about him. Knuckles is relieved that the opossum with them isn't the Bike Chain Bandit, but he is soon proven wrong, as the Bike Chain Bandit tries to choke him with a bicycle chain, causing him to swerve. Knuckles tells Sonic to help him, and Sonic kicks the Bike Chain Bandit out of the Dude-Mobile. Sonic then tells Knuckles that he's driving again, and Knuckles stops the Dude-Mobile. The Bike Chain Bandit catches up to Sonic, Tails, and Knuckles, and Sonic and Knuckles quickly swap seats. Sonic drives away, leaving the Bike Chain Bandit behind.
The next morning, as Sonic passes by another 60-Miles-Per-Hour Speed Limit sign, he gets pulled over by the Police Officer again. Sonic tells the Police Officer that the Bike Chain Bandit is in the back of the Dude-Mobile, and the Police Officer sees the Bike Chain Bandit's bag near Knuckles. The Police Officer thinks that Knuckles is the Bike Chain Bandit, and tells Sonic that he knew he, Tails, and Knuckles were up to no good. As Sonic tries to tell the Police Officer who he is, the Police Officer handcuffs him and tells him he's under arrest.
In a nearby jail cell, the Police Officer tells Sonic that he gets one phone call, and he should make it a good one. Sonic calls Amy, and tells her that he, Tails, and Knuckles are in jail, and they need her and Sticks to bail them out. As it turns out, Hedgehog Village is under attack, and Amy tells Sonic that she is not in the mood for his practical jokes, as she and Sticks have problems of their own. Amy hangs up, and the Police Officer assures Sonic, Tails, and Knuckles that they'll be spending the night in the Grey Bar Hotel. Tails is relieved, as he thought that they'd be spending the night in jail, only to realize they really are spending the night in jail. Just then, a shadow casts over them. The shadow is revealed to belong to Salty, who used to be Justin Beaver's bouncer. He recognizes Sonic, Tails, and Knuckles as the Dreamboat Express band, and he's a big fan. Tails tries to explain to him that he, Sonic, and Knuckles now go by "Dude-itude", but Sonic silences him and tells Salty that they are Dreamboat Express. Salty tells Sonic, Tails, and Knuckles that the Police Officer has been arresting innocent citizens since the Bike Chain Bandit escaped, and when he heard about his chain-wallet business, they arrested him. Sonic tells Salty that he, Tails, and Knuckles know what the Bike Chain Bandit looks like, and if he can help them escape, they can help him catch him and clear their names. Salty tells Sonic, Tails, and Knuckles that he'd be happy to help them escape, and Sonic tells him to distract the Police Officer. Sonic then realizes that all he needs in an inconspicuous, yet surprisingly powerful magnet, and Tails reveals that he has an industrial-strength micromagnet that he keeps hidden on his person at all times. Sonic decides it will have to do, and the Police Officer comes in with stew. Salty distracts him by telling him he needs a vegetarian meal, and knocks the tray out of his hands. As the Police Officer is distracted with it, Tails uses his magnet to get the keys, and the keys to unlock the cell. He, Sonic, Knuckles, and Salty all escape. The Police Officer tries to chase after them, but slips on the stew and falls over.
Sonic, Tails, and Knuckles make it back to the Dude-Mobile, and the Police Officer chases after them. Tails sees the Police Officer, but instead of pulling over, he decides to evade him. Meanwhile, the Bike Chain Bandit roams the desert, when he suddenly hears the Police Officer's siren. Sonic, Tails, and Knuckles catch up to the Bike Chain Bandit, who comes across Mrs. Vandersnout, who is looking over her map. He pushes her off her motorcycle and drives it away. He, Sonic, Tails, Knuckles, and the Police Officer come to an erupting volcano, and they all split up. Tails tells Sonic that the Bike Chain Bandit is getting away, but Sonic assures him he's on it. Sonic then reveals that he has the Blue Force One in the back of the Dude-Mobile, and he uses it to float over the lava. Tails then comes to a ramp, and speeds the Dude-Mobile up to jump across the lava. The Police Officer jumps off the ramp, but falls off his motorcycle and is about to fall into the lava. Tails sees him and saves him with an enerbeam. Sonic catches up to the Bike Chain Bandit, and tosses a chain that the Bike Chain Bandit left behind into the wheel of Mrs. Vandersnout's motorcycle, knocking the Bike Chain Bandit off of it and causing him to land near the Police Officer, who promptly arrests him. The Police Officer then tells Sonic, Tails, and Knuckles that he was wrong about them; they're not low-life hooligans, they're law-abiding hooligans, and have been pardoned of all criminal charges.
When they get back on the road, Sonic tells Tails to hurry if they still want to make it in time for their concert. When they arrive, they find the stage empty, save for the janitor, who's cleaning it. Knuckles asks him if they missed the concert, and in an interesting twist, the janitor tells them they're a whole month early. Sonic and Knuckles stare angrily at Tails, who nervously tells them that he must have been so excited, he didn't pay attention to the date. He then tries to cheer them up by telling them that the site of the world's oldest rock is two hours away. Sonic angrily tries to attack Tails, with Knuckles holding him back.
This episode provides examples of:
- Call-Back: Sonic's band, Dude-itude, from "Battle of the Boy Bands", gets booked for a concert in this episode. When Sonic and Knuckles are unfamiliar, Tails gives a brief recap of the episode's events.
- Chekhov's Volcano: Shows up in the episode's climax.
- Coincidental Broadcast: The radio station playing on the Dude-Mobile interrupts its regular broadcast of silence to warn the listeners about the escaped Bike Chain Bandit almost immediately after Sonic and Tails find out that Knuckles picked him up.
- Comically Missing the Point: After Sonic uses his one phone call on Amy, the Police Officer tells him that he, Tails, and Knuckles are spending the night in the grey bar hotel. Tails is relieved, and says he thought they would be spending the night in jail, only to realize they are spending the night in jail.
- Hoist by His Own Petard: The Bike Chain Bandit leaves his duffle bag of chains in the Dude-Mobile. During the episode's climax, Sonic tosses one of the chains into Mrs. Vandersnout's motorcycle, stopping the Bike Chain Bandit in his tracks.
- Hostile Hitchhiker: The Bike Chain Bandit, an escaped criminal described by a radio broadcast as a large, snaggle-toothed opossum wearing a trenchcoat, and carrying a duffle bag filled with bicycle chains. Knuckles picks him up, figuring he needed company while he drove the Dude-Mobile and Sonic and Tails were sleeping. The Bike Chain Bandit attempts to choke Knuckles with a bicycle chain while he is still driving, but is kicked out of the Dude-Mobile by Sonic. Near the end of the episode, Sonic, Tails, and Knuckles help a police officer who had earlier arrested them capture and arrest the Bike Chain Bandit.
- Mythology Gag: When Sonic complains about getting another speed ticket, he mentions that the court probably won't accept "Gotta Go Fast" as a medical condition, referring to a meme from the Sonic X theme song.
- Noodle Incident: When Sonic gets a speeding ticket, he mentions this isn't the first time this has happened to him.
- One Phone Call: When Sonic, Knuckles, and Tails get arrested, Sonic tries to call Amy so she can bail them out. Not only is Amy in the middle of a battle, she thinks he's prank calling her and hangs up.
- Potty Emergency: Knuckles has two of these.
- Selective Magnetism: Tails uses an industrial-strength magnet to get the keys to the jail cell that he, Sonic, Knuckles, and Salty are in.
- "Shaggy Dog" Story: By the time Sonic, Tails, and Knuckles get to their concert, the stage is empty, save for a janitor sweeping it. In an interesting twist, they actually aren't late to the concert at all. In fact, they're an entire month early.
- This episode's title is a reference to the 1987 film, Planes, Trains and Automobiles.
- The scene where Knuckles picks up the Bike Chain Bandit is a reference to a similar scene in Tiny Toon Adventures: How I Spent My Vacation, where Hamton's family picks up Mr. Hitcher.
- The music that plays in the background sounds remarkably similar to the song, "Push it to the limit", which was also used in the previous episode, only without the somewhat-motivational lyrics.
- Sure, Let's Go with That: Salty recognizes Sonic, Tails, and Knuckles as the Dreamboat Express band, and that he's a big fan. Tails tries to explain to him that he, Sonic, and Knuckles now go by "Dude-itude", but Sonic silences him and tells Salty that they are Dreamboat Express.
- Synchronous Episodes: This episode's events run parallel to those of "Sticks and Amy's Excellent Staycation", as evidenced by certain lines and events being the same in both episodes.