The dynamic arcs of travel illustrated on this map are signs of a new era. Before the Civil War, many of the relocations of Monticello’s African Americans and their descendants were enforced journeys made by still-enslaved people. Even those who were free, like the Hemingses and the Fossetts, were impelled to leave Virginia by the worsening conditions for free blacks there. From 1865, an expanding transportation network made travel easier and everyone was free, free to choose their residences, free to seek a better life for their families.
Moses Gillette left Virginia after Emancipation to settle in Ohio near his brother Israel Gillette Jefferson. Yet the search for greater opportunity led to separation as well as reunion. Several descendants left the Ohio heartland for cities on the East and West Coasts. Madison Hemings’s youngest daughter, Ellen Hemings Roberts, broke the pattern of her family members by leaving rural Ohio for a western city. Her enterprising husband, Andrew J. Roberts, prospered in the booming city of Los Angeles. Virginia and Maria Isaacs left their Ohio farm to live in Boston with their husbands, James Monroe Trotter and William H. Dupree, who had served in the 55th Massachusetts infantry regiment in the Civil War. As the only fully-commissioned black army officers in Boston, they were conspicuous figures with a broader choice of careers than most black men. They joined the U. S. Postal Service as clerks, pioneers in one of the few white-collar workplaces then open to African Americans.
Eston Hemings Jefferson’s son John Wayles Jefferson was so taken with the rich cotton plantations he had seen when fighting the Confederates in the war that he left his family in Wisconsin to live in Memphis, Tennessee. He became a very wealthy cotton broker and plantation owner there. His brother Beverly Jefferson’s sons and nephew migrated from Wisconsin to the fastest-growing city in the nation, Chicago, to pursue their careers in business, law, and medicine. One became a millionaire.