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. 

Situated on a peninsula jutting into picturesque Casco Bay, Portland has long been admired for its geographical setting—the “beautiful city by the sea,” as native son Henry Wadsworth Longfellow called it. At the same time, Portland's deep, ice-free port has made it an ideal site for the development of coastal commerce and industry. Much of the city's history, John F. Bauman shows, has been defined by the effort to reconcile the competing interests generated by these attributes—to balance the imperatives of economic growth with a desire to preserve Portland's natural beauty.

Caught in the crossfire of British and French imperial ambitions throughout the colonial era, Portland emerged as a prosperous shipbuilding center and locus of trade in the decades following the American Revolution. During the nineteenth century it became a busy railroad hub and winter port for Canadian grain until a devastating fire in 1866 reduced much of the city to ruins. Civic leaders responded by reinventing Portland as a tourist destination, building new hotels, parks, and promenades, and proclaiming it the “Gateway to Vacationland.”

After losing its grain trade in the 1920s and suffering through the Great Depression, Portland withered in the years following World War II as it wrestled with the problems of deindustrialization, suburbanization, and an aging downtown. Efforts at urban renewal met with limited success until the 1980s, when a concerted plan of historic preservation and the restoration of the Old Port not only revived the tourist trade but eventually established Portland as one of America's “most livable cities.”