South to receive the "All Aboard Wasteland Conductor" pin as a reward.
To earn the Off Track achievement/trophy simply do not fix any of the train stations, then after finishing the main storyline, go back and visit each train conductor. You have to repair all of the stations, before aftershocks destroy all of them (but please be aware that the Wii game is glitched, making it impossible to complete both in one game file).
Mean Street South
The train conductor is in a booth right up against the initial entrance to Mean Street. He explains that a fan has gone haywire, but could probably fixed with a Watch Sketch, and darned if the Emporium doesn't just happen to have some of those in stock.
Head over the Emporium and purchase a watch sketch, then return to the train station and stand on the crates just in front. Use the watch sketch while standing on the crates, then Oswald should jump into action, and fix the fan.
The Conductor tells Mickey that the quakes have collapsed the OsTown Train Station and he needs Mickey's help to stretch it back into shape and paint it.
Jump up on the very top of the roof and use the Fairy Sketch to raise the roof up, then paint the whole place and speak to the Conductor again to get a reward.
While the train conductor is found and spoken to during Mickey's first visit to Bog Easy, this quest doesn't become available until a second visit.
Find the train conductor in New Town, Bog Easy. He complains that he'd rather sit around and watch TV than do his job, but unfortunately he lost his TV in the quake.
Mickey will need the TV sketch to finish this quest. It can be purchased from the shop here in Bog Easy.
Approach the wooden platform next to the train station and let Oswald do his thing to power it up. Now use the TV sketch to lure the train conductor to the station. This is easier if the TV sketch upgrade has been purchased (can be found in the Bog Easy shop). Drop a TV somewhere between the station and the Train Conductor. If its not too far away, he'll walk towards the TV. Repeat this until he decides to get back to work and rewards Mickey with a pin.
Speak to the train conductor in the station next to the TV station. He'll moan about the station being blocked by debris, and suggest using an anvil to clear it. Get the anvil sketch from Tiki Sam's shop, then return and drop one on the debris. Speak to the train conductor again to get a pin.