About one in ten refugees from the American Revolution was African-descended, and unlike many white Loyalists fleeing war in the thirteen mainland North American colonies, black Loyalists were people without a country. Most were fleeing slavery in Virginia or the Carolinas, yet not fully able to claim to be British subjects, despite many heeding the call to join British forces. Among the 40,000 Loyalists who departed, around 3,500 black Loyalists evacuated from the newly founded United States between the years of 1776 and 1785. I hope to evaluate the movement patterns and thought process behind this particular group with what choices they ultimately had after the war using Dunmore’s Proclamation as a means to freedom. These black Loyalists faced the difficult decision in choosing what identity they would side with once they left. These former slaves ultimately had to choose between becoming forced migrants with the losing side of the war or staying with the winning side of the war as people bound by chains. Although there were a multitude of fascinating tales that could be told through the lens of these black Loyalists, one particular family caught my eye within my research. This story is the journey of the Fortune family who chose to run away from American slavery to migrate to Nova Scotia. Their story will grant me access to analyze the extreme discrimination families met as they fled, the contempt the new colonies felt against them, as well as the evolution of their societal roles as some of these immigrants integrated into their new country and became accepted as respected individuals. Furthermore, their tale aided me in understanding what caused some emigrant black Loyalists to stay in Nova Scotia despite the hardships they faced as outsiders who were unwelcome from the perspective of native white Nova Scotians.