With the mention of Kenny Roger's Gambler in an earlier entry I couldn't help noticing how many railway songs seem sad.
There's Kenny's other favourite "The Green, Green Grass" which mentions
"The old hometown looks the sameAs I step down from the train
And there to meet me is my mama and papa
And down the road I look and there runs Mary
Her golden lips like cherriesIt's good to touch the green, green grass of home."
And you might think that's cheery until you listen to the rest of the song and realise that he's dreaming and when he wakes he will remember that he is about to face the Death Sentence.
I can also think of "Midnight Train to Georgia" which isn't the world's cheeriest song, although at least they go back to live happily ever after.
On the other hand I've never seen Starlight Express but according to the wikipedia entry that seems to have a happy ending. And we cannot forget "Chatanooga Choo-Choo" - that's quite cheery (and you can even go to Chatanooga and stay in a Holiday Inn Railway Carriage!)
If anyone has any ideas feel free to add them in the comments