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Tens of thousands of Black North Americans returned to the United States during the Civil War, Reconstruction, and in the decades that followed—while thousands of others migrated north into Canada in these years. These short chapters, drawn from a book nearing completion, will examine how some border-crossing families were able to seize educational or economic advantages through migration, even in the years when legal racism was the norm in both countries. Tracing a handful of families, they will emphasize the different paths in freedom that border-crossers made.