This song was written by a MacGregor of Glen Endrick, who was jailed, along with a friend, in Carlisle, England in 1746.  The author had been condemned to a grisly death for his support of Bonnie Prince Charlie in the 1745 uprising, while his friend was being set free.

The song tells of the old Celtic myth that the soul of a Scot who dies outside his homeland will find its way back to Scotland by the spiritual road, or the low road; so he tells his friend "You take the high road and I'll take the low road . . . "

The original song was written in Gaelic and was sent to his wife back home.  It was later translated to English.  Nevertheless, it still imparts a profoundly haunting effect on the listener and has become a classic love story for the ages.