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Glen Fruin ("Glenn a Bròn" in Gaelic, meaning Valley of Sorrow), on the southwest side of Loch Lomond, was the site of an ambush by the Colquhouns and their allies against a force half their size of MacGregors. The MacGregors were triumphant, and massacred the Colquhouns. This overwhelming victory resulted in the first proscription of the MacGregors, leaving our clan to be treated worse than wild beasts for 47 years, until 1650, when Oliver Cromwell's English army successfully defeated Scottish Royalist troops and took Edinburgh.

Cromwell's rescinding of the MacGregor proscription was not due to a particular affection for the MacGregors. It was due to his hatred of fanaticism in all its forms. This repeal was upheld by Charles II when he came to power in 1660. However, MacGregor properties were never returned to their rightful owners.