The Battle of Glendale was fought on the Inner Hebridean Isle of Skye when the MacDonalds of Sleat and the MacDonalds of Clanranald clashed with the MacLeods of Harris and Dunvegan and the MacLeods of Lewis. According to MacLeod tradition preserved in the early 19th century, the battle was fought in about the year 1490, though more recent scholarship suggests that the battle more likely took place sometime after 1513. MacLeod tradition records that the battle was the 'most tremendous battle' that the clan ever fought—although the clan was victorious, it never fully recovered from its severe losses. MacLeod tradition also relates how the MacDonalds originally had the upper hand during the conflict, but when Clan MacLeod's sacred Fairy Flag was unfurled the MacLeods gained heart and won the battle.
According to MacLeod tradition preserved in the Bannatyne manuscript, a force of MacDonalds led by Donald Gruamach MacDonald landed on Skye at Loch Eynort in about the year 1490. The MacDonalds proceeded to lay waste to the lands of Minginish, Bracadale, and Duirinish, and their forces got right up to the gates of Dunvegan Castle. The manuscript states that during this time, the chief of the MacLeods of Harris and Dunvegan, Alasdair Crotach, was on Harris, but that upon hearing the news of the MacDonald's encroachments, he proceeded with all haste to Skye. The manuscript states that he landed at Glendale, where he was joined by his kinsmen, the MacLeods of Lewis. The historian J. L. Roberts noted that they would have landed at the head of Loch Poolteil, where the Glendale valley reaches the sea. The manuscript relates that the combined MacLeod forces drew up on the brow of a hill, with a river in front of them which made it difficult for the MacDonalds to attack.
The Bannatyne manuscript relates how the combined MacLeod forces waited ten days for reinforcements, until Donald Mor of Meidle arrived with a large force under his command. The battle then commenced; the MacDonalds, however, gained the upper hand as Donald Mor was killed and hundreds of the MacLeods were killed. The MacLeods were just at the point of giving way when the mother of Alasdair Crotach ordered the Fairy Flag to be unfurled. With the magical flag unfurled, the manuscript states that the battle was renewed with redoubled fury, with immense losses on both sides. At one point, a party of MacDonalds, led by Allan MacDonald of Moidart (chief of the MacDonalds of Clanranald), managed to cut off the MacLeod chief and the guardians of the Fairy Flag from the rest of their clan. However, just at that moment, Murdo MacCaskill slew Donald Gruamach MacDonald, raised his head upon a spear and ordered the MacLeod pipers to play the MacDonald lament. Disheartened by the ill-omened music and the loss of their leader, the MacDonalds broke and fled, disregarding attempts by the Clanranald chief to rally them.
The site of Battle of Glendale (Skye) lies on Unnamed Extrusive Rocks, Palaeogene, bedrock that formed in the Paleogene. The rock here is mafic lava and mafic tuff.
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