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Free blacks in Trinidad during the late nineteenth century took to the streets of Port of Spain painted in extravagant colors and dressed up in miraculous costumes. Simulating the horrors of slavery in a playful manner was a provocative symbol that the elite plantocracy and the British colonial government on the island detested. These party participants continued this practice known as Canboulay every year on the night before Carnival. This determination, despite intense opposition from the ruling classes was certainly a remarkable act and symbol of defiance. What historians of Trinidad have neglected is to make the connection between the importance of the Canboulay Riot of 1881 and the implications the riot itself had on the future and evolution of Carnival as a larger celebration.1 Most notably, the integration of the middle class into Carnival can be attributed to this riot. Moreover, historians have yet to explain why changes in Carnival came about through violence in Trinidad, yet occurred naturally and peacefully throughout the rest of the Anglophone Caribbean. This essay seeks to correct this oversight by analyzing the early years of Trinidad’s Carnival, and to present distinct differences between Trinidad, and the other Caribbean islands that have adopted this celebration.