Built on an investigation of a large number of archival sources in three different countries, this study analyses free, non-white communities in the circum-Caribbean. Using the comparative method, I assess how the Maroons and Creeks negotiated a role for themselves in an inter-war context, exploring their interactions with four main groups. First, I consider the Maroon and Creek relationship with the enslaved population of Jamaica and the United States, respectively. This allows me to demonstrate that the signing of the peace treaties with white society had little impact on interactions with slaves. Maroon and Creek attitudes towards slaves continued in much the same manner as before peace, it was the contexts in which these interactions that took place which changed. Second, I scrutinise how the two communities navigated the potentially inflammatory situation of peace with their former white enemies. I argue that the Maroons enjoyed a more amicable relationship than the Creeks did with the local white settlers. This was largely a result of the fact that the Maroons and local whites shared a mutual usefulness whereas the Creeks and local whites did not. Third, I compare the Maroon alliance with the colonial government of Jamaica with that of the Creek and federal government. I show that, initially, both governments appreciated the usefulness of such an allegiance but, as time passed and the Maroons and Creeks showed no indication of submissiveness, both soon moved to restrict, and ultimately reduce, the independence of the societies. This attitude was exacerbated following the Haitian Revolution when the perceived threat to white stability from the Maroons was at its height and the white desire for Creek lands was increased with the Louisiana Purchase. Finally, I examine the degree of Maroon and Creek interactions outside the borders of Jamaica and the United States. I show that both were fully incorporated into the circum-Caribbean region both before and after the peace treaties. Whilst the Maroons encountered European powers prior to the treaties, this ceased with the coming of peace and their alliance was focused on the British. However, the fears of the colonial government, particularly after the Haitian Revolution, ensured that the Maroons would be plagued by rumours of foreign collusion throughout the eighteenth century. In ii contrast, the Creeks continued their numerous communications with European powers after the ending of hostilities. American fears were based on very real events. As a whole, my PhD thesis challenges the current strict hierarchical conception of race in the circum-Caribbean. The similarities between the Maroons and Creeks highlight the fact that non-white experiences were often determined by free status and the cause of many of the differences was the different ‘frontier’ context of the two rather than their divergent racial backgrounds.