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Folklore suggests that The Bonnie Banks of Loch Lomond 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 death for his support of Bonnie Prince Charlie in the 1745 Jacobite uprising, while his friend was going to be set free. The song tells of the old Celtic myth that the soul of a Scot who dies outside his homeland will find it's way back home by the spiritual road, or the low road. So the condemned man says to his friend: "You take the high road and I’ll take the low road, and I’ll be in Scotland afore ye..."
Loch Lomond is an old Jacobite Air. It is based on an older folk tune Robin Cushie (Kind Robin Loves Me), in McGibbons Scots Tunes Book I, dated 1742. The words are attributed to Lady John Scott (1810-1900). The version we are familiar with today is said to have first appeared in print in Poets and Poetry of Scotland (1876).