Loch Lomond (legend of the song By Yon Bonnie Banks).
There are many theories about the meaning of the song. One interpretation
is that it is attributed to a Jacobite Highlander who was captured after the
1745 rising. The English played games with the Jacobites, and said that one
of them could live and one would die. This is sung by the one who was sentenced
to die, the low road referred to being the passage to the underworld. Some
believe that this version is written to a lover who lived near the loch.
A related interpretation holds that a professional soldier and a volunteer were captured by the English in one of the small wars between the countries in the couple hundred years prior to 1746. Volunteers could accept parole, a release contingent on the volunteer's refusal to rejoin the fighting, but regulars could not and so could face execution. The volunteer would take the high road that linked London and Edinburgh while the soul of the executed regular would return along the "low road" and would get back to Scotland first.
Another interpretation is that the song is sung by the lover of a captured rebel set to be executed in London following a show trial. The heads of the executed rebels were then set upon pikes and exhibited in all of the towns between London and Glasgow in a procession along the "high road" (the most important road), while the relatives of the rebels walked back along the "low road" (the ordinary road travelled by peasants and commoners).
It captures some of the romantic spirit of the lost cause of Bonnie Prince Charlie