Guy Clark - Desperadoes Waiting For a Train It's not soley about trains, but it's a badass song and has been covered by numerous artists including the Highwaymen.
Texas-1947 - Guy ClarkTrain #10 - Tim McGrawRunaway Train - Dale WatsonCity of New Orleans - Willie NelsonI Heard That Lonesome Whistle Blow - Hank WilliamsWabash Cannonball - Roy AcuffEngine 143 - The Carter Family If I remember right this was the last song Johnny Cash recorded, too. (edit:
Wikipedia says it was)
Like The 309 - Johnny Cash
Hey Porter - Johnny Cash
Rock Island Line - Johnny Cash
Orange Blossom Special - Johnny Cash Actually, Johnny Cash has a concept album titled
Ride This Train. The songs aren't about trains, but in between tracks he tells stories over the sound of a locomotive.
I'll save a few for everyone else to mention
