The song has often been dated to 1746, and it has long been associated with the Jacobite rebellion. In December 1745, Bonnie Prince Charlie retreated to Scotland, and the lyrics have been interpreted as a lament of the march.[4] One of the soldiers rues his sacrifice for the king.[5] In Celtic mythology, the "low road" was a fairy route for a soldier's soul to return home when killed abroad.[6]

Another common interpretation is that the chorus are the final words spoken by one of the Jacobite rebels prior to his execution, perhaps in Carlisle where dozens of rebels were executed.[7][8]: 276  He sees his lover at the gallows and tells her they will meet again in Scotland, albeit by different routes.[9] Ironically, the song became one of a handful of folk signifiers for British unity as the nation expanded its empire.[10]

One of the earliest sheet music printings of the ballad was in 1840 by Paterson and Sons in Edinburgh. It was titled "Bonnie Loch Loman" and credited to "a lady" with arrangements by Finlay Dunn and John Thomson. Lady John Scott was often cited as the composer of "Loch Lomond", but she only transcribed the melody and lyrics after hearing it sung by a boy in the Edinburgh streets.[11] In his 1898 novel Wild Eelin, William Black has the title character, Eelin MacDonald, directly refute the idea that a street urchin in Edinburgh would ever sing the song, dismissing it as "spurious".[12]: 86–7 

The actual composer is unknown. Precedents for the tune have been found in several other folk songs, such as the Danish/Faroese tune "Dankonning lod gribe en havfrue fin" (The Dane-King Captured a Mermaid).[13] "Loch Lomond" along with "The Oak and the Ash" also bear a resemblance to "Godesses", a tune in John Playford's 1651 compilation The Dancing Master.[14][15]