The Northern and Western Isles of Scotland were closely connected during the Norse period. Both were part of the Kingdom of Norway and the Archbishopric of Nidaros, and indeed, for extensive periods, all these islands were ruled by Jarls of Orkney, such as Sigurr the Stout and orfinnr the Mighty. The situation changed with the hand-over of the Hebrides to Scotland in the Treaty of Perth of 1266. The Hebrides were annexed to the Scottish realm, while the Northern Isles remained Norwegian. A cultural and political wedge was driven between the island groups, and connections between the two areas become much harder to identify in the record. However, connections there were, usually, but not always, in the form of violent raids waged against the Northern Isles. The modern folklore of both Orkney and Shetland still contains references to raids by Lewismen. A Lewis Scord (hill pass), where Lewis raiders were slaughtered and buried, can still be identified by locals at Scousburgh in Shetland today. In this paper, I have taken folklore seriously as an historical source. Folklore can be problematical as it is notoriously difficult material. It also raises justified suspicions in the minds of the critically schooled historian. However, there is an ulterior purpose: because in this case elements of folklore can be traced back to actual, recorded events, I wished to show that folklore should not be dismissed out of hand, especially where oral tradition is strong and other sources in short supply. The paper provides a small demonstration of the value of folklore, but it also shows how changes in folklore and errors in the transmission of the story can be traced through time. This paper focuses on the ramifications of a hitherto unremarked marriage between two of the most powerful figures in 16th-century Orkney and Lewis: Lady Barbara Stewart, widow of James Sinclair of Brecks, and Ruaraidh Mac Leod, Chief of the Sìol Torcail and Baron of Lewis. The reality of Scottish historiography is that scholars of the Northern Isles and the Hebrides have not always been aware of the history of each other's islands. So perhaps it is not surprising that this marriage has effectively slipped under the historians’ radar. However, it could provide hitherto unrecognized evidence of intimate elite contact between Northern and Western Isles in the mid-16^th century and a possible attempt to extend MacLeod Lordship to Orkney and Shetland.