Lyric discussion by Inyarear 

Cover art for 500 Miles lyrics by Peter, Paul and Mary

This song is done in the style of many old negro spirituals, many of which had a double meaning in aiding the escape of slaves. This one sounds more like a marching tune for escaped slaves to be singing on the road, though, since the meaning would be difficult to mistake. (My interpretations are in parentheses.)

If you miss the train I'm on (the Underground Railroad), you will know that I am gone (I've run away from Master) You can hear the whistle blow a hundred miles (That's how far the local slave-catchers will chase me)

...

Lord I'm one, Lord I'm two, Lord I'm three, Lord I'm four, Lord I'm five hundred miles from my home (That's roughly how far it is to the Free States/Canada)

...

Not a shirt on my back, not a penny to my name (This is a grueling journey) Lord, I can't go home this-a-way (because if I do, Master will beat me to death)

Song Meaning

@Inyarear This so nothing to do with slavery but it can work as a metaphor for slavery. It’s about railroaders. Watch Rocky Mountain Express (on 4k or regular Blu Ray.) It’s incredible.