Pure speculation - I have a suspicion that this was once "it's shorter to hell for Alighieri", as in Dante Alighieri and his journey to hell. To my mind the lyric suddenly makes sense with this substitution, as in "this journey is so long and wearing that even Dante's journey through hell must have been shorter and easier.

It's a bit 'literary' for a cowboy song, but I can imagine it as the kind of fragment of history/culture to filter in like this, in roughly the same way as the St. James Infirmary in London has become iconic in American jazz though 'the folk process'.