Comparing investment in transportation companies in Albemarle county, Virginia, and Cumberland county, Pennsylvania, I analyze why nineteenth-century internal improvements revolutionized the northern economy, but only seemed to increase the South's dependence upon plantation agriculture. In both counties local investors and state governments financed early improvements. Beginning in the 1830s, however, urban capitalists financed most Pennsylvania railroads, leading to the eventual integration of railroads into coherent systems. Local investors and the state government continued to dominate Virginia's railroads, which made it difficult to build improvements to pierce the Appalachians and link the Old Dominion to midwestern markets.