The bridge standing here dates to 1929, but the effort to span the Kentucky River gorge began much earlier, when merchants in Lexington and Cincinnati sought a direct route to Southern markets that avoided shipment by the Ohio and Mississippi rivers. In 1854, the Lexington and Danville Railroad hired engineer John A. Roebling to bridge the river, but only the massive stone towers for his suspension bridge were finished before the railroad failed in 1858. Nearly twenty years later, the Cincinnati Southern Railroad successfully built a new bridge without using Roebling's towers. Charles Shaler Smith, chief engineer for the Baltimore Bridge Company, designed and built a cantilever bridge, the first in North America. When it opened in 1877, the bridge stood 275 feet above the river and was the highest bridge in North America, the longest cantilever bridge, and the highest railroad bridge in the world. High Bridge became an engineering marvel that drew scores of visitors, with special excursion trains running to the overlook, and by 1879 this site had a pavilion, restaurant, picnic grounds, and riding stable that made High Bridge Park the center of social and cultural life in Jessamine County. In 1911, the American Bridge Company rebuilt and strengthened the bridge around the existing structure without interrupting service, increasing it to withstand a dead load of seven tons per linear foot. Roebling's stone towers remained until High Bridge was double tracked in 1929.