Raasay's history stretches back to the Gaelic Kingdom of Dalriada in the 6th century, when the island was part of the Celtic world that stretched from Ireland to the western seaboard of Scotland. In the 8th century it became a Norse subject, and the name Raasay itself comes from the Old Norse raas-ey, meaning "Isle of the Roe Deer," a testament to the red deer that still roam its hills. The island returned to the Kingdom of Scotland in 1266, but its character remained Gaelic and Hebridean, shaped by the sea and the wind and the narrow stretch of water called the Sound of Raasay that separates it from Skye.

The island's most ancient spiritual site is Tobar na Ba Bàine, the Well of the Pale Cow, which has been known since Celtic and Iron Age times. The pale cow was a figure of fertility in early Celtic belief, and the well that bears her name still flows, filtering through volcanic rock and Jurassic sandstone to emerge as the water source that gives character to every dram distilled on the island today. The well sits near the site of Borodale House, where a natural spring has served the community since before recorded history. In an island where the population has dwindled to a few hundred, the well remains a living connection to the deep past, a reminder that Raasay was a place of sacred water long before it was a place of clan warfare or romantic poetry.

The MacLeods of Raasay ruled the island from the 15th to the 19th century, their seat first at Brochel Castle, a fortified clifftop stronghold in the north, and later at Raasay House in the sheltered woodlands of Clachan in the south. Iain Garbh, the rugged MacLeod chief, was the last to hold the northern seat at Brochel, distinguished among his contemporaries for his size and strength. The move from Brochel to Clachan in the 1700s marked a shift across the island, from facing east across the seas to Wester Ross to looking west toward the Cuillin mountains of Skye, and it mirrored the broader change across the Highlands as clan chiefs began adopting Lowland landlord values over the bonds of community kinship. The MacLeods held the island through centuries of peace and war, but their loyalty to the Jacobite cause in 1746 would bring ruin.

When Bonnie Prince Charlie fled after the Battle of Culloden, he spent two nights hiding on Raasay. The MacLeods had supported the Stuart claim, and when Hanoverian troops discovered this, they descended upon the island with a fury that matched the brutality of the clearance years. The MacLeods of Raasay suffered retribution that stripped them of everything: their livestock was killed, their homes and boats were looted and razed, and the island was left scarred. A century later, the Highland Clearances would finish what Culloden had begun. The population of Raasay, which had once numbered over a thousand, was driven from the land by landlords who found sheep more profitable than people. The north of the island, deemed unfit even for sheep, was emptied entirely, and the communities that had lived there for generations vanished into the cities and the New World.

From this devastation came one of the most powerful voices in Gaelic literature. Sorley MacLean was born on Raasay in 1911, and his poem Hallaig, named after a cleared township on the island's north coast, became the definitive expression of Highland grief. The poem speaks of the dead who walk the empty glens, the girls who left and never returned, the houses that stand roofless against the wind. MacLean's work ensured that Raasay's tragedy would not be forgotten, and his legacy draws lovers of Gaelic poetry to the island still. In the 20th century, another Raasay man, Calum MacLeod of Arnish, achieved a different kind of immortality. When the road ended three kilometres from his village and the authorities refused to extend it, he spent ten years building Calum's Road by hand, using only a pick, a shovel, and a wheelbarrow. The road was completed in the 1960s, and today it stands as a monument to the determination of island life, a track that connects the north to the south and the past to the present.