Reuben Ruby and Nathaniel Gordon II were born eleven months apart in 1798 and 1799 and spent much of their boyhoods roaming the noisy, bustling waterfront of Portland, Maine. They lived just blocks from one another, attended school together, and went to the same church with their families. But they were worlds apart, separated by family, culture, and race. Reuben Ruby was Black and Nathaniel Gordon was white.  The Rubys became prominent antislavery activists, equal rights advocates, and operatives on the Underground Railroad. Their neighbors, the Gordons, became well-to-do ship masters, owners, and merchants: among them, the most notorious American slave ship captain of the century, Nathaniel Gordon III. As activists, sea captains, businessmen, prospectors, and politicians, members of these two families traveled to New York, California, Texas, Louisiana, Africa, Haiti, and Brazil, where their experiences were shaped by their racial identities. At home in the “Free North,” they faced social and political divisions nearly as sharp as those they encountered elsewhere.  To understand the issues that divided nineteenth-century America—and, in many ways, still divide the nation—few have looked to the far North. In this compelling narrative history and intimate dual-family biography, Carol Gardner traces the Rubys and Gordons as they navigate the turbulent 1800s. As families and individuals, they demonstrate that the North was a critical proving ground for American notions of freedom and equality, as telling as any town, plantation, or battlefield in the South. Their experiences help reveal what it meant to live in a free state during the age of slavery, with all the promise, disappointment, irony, and hope that the notion entailed.