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Freetown was founded in 1792 by formerly enslaved Black Americans, Nova Scotian Settlers who had fought with the British during the American Revolution and been promised freedom in return. They arrived on the Sierra Leone peninsula, gathered beneath a massive cotton tree in what is now the heart of the city, and named the settlement for the freedom they had come to claim. That Cotton Tree, a centuries-old kapok in the centre of downtown, still stands on the corner of Siaka Stevens Street and Lightfoot Boston Street, and it remains the most powerful symbol in a city built on acts of radical self-determination.

The City is a major Atlantic port on a peninsula of dramatic green hills descending steeply to the harbour, and the drive or walk up to Hill Station offers views across the water that help explain why this compressed geography produced a city of such density and creativity.

The Sierra Leone Creole people, descendants of the original settlers and subsequent groups of liberated Africans, developed a culture, cuisine, and hybrid language that is distinctly West African but carries the marks of its unusual Atlantic origin. Freetown was also for a time the capital of British West Africa, which explains the presence of West Africa's first hospital, Connaught Hospital, and several other firsts of the colonial era.