Bridges at this Embarras River crossing on the National Road changed repeatedly from 1830 to 2001. An original Jackson Truss bridge, inspected in 1833 and discussed in a War Department report dated May 14, 1834, had oak and black walnut in the superstructure, substantial masonry, and an enlarged span after the first west abutment foundation failed near the river; its estimated cost was $8,300 and its actual cost was $11,700. That timber bridge washed out in 1865, and between 1865 and 1875 ferry service at the site was operated by Mr. Workman, Sam Cisna, Chas Allen, R.M.G. Cleghorn, and John Hallett, with Workman also running a pontoon bridge for a time. In 1875 Cumberland County contracted with McKay and Nelson Iron Bridge Company of Fort Wayne, Indiana, to build a pin-connected Pratt Truss iron bridge for $9,700; it was condemned in 1896, repaired after Greenup agreed to pay half the expense, and permanently closed in 1912, after which intermittent ferry service returned until 1920. In 1920 the Illinois Division of Highways built a three-span concrete thru girder bridge using the earlier steel truss bridge abutments, but flooding in 1996 exposed a scour hole under the east pier and, along with the poor condition of the deck and hand rails, led to its immediate closure. Debate followed over whether to remove the crossing, but local citizens and Greenup officials supported replacement as part of efforts tied to the Greenup Historic Business District and National Scenic Byway plans. Research confirmed that a Jackson Truss covered bridge had originally stood here, funds for design and construction were secured in 1997, and a new bridge designed by Elmer G. Pyle of Rhutasel and Associates was built by O'Neil Brothers Construction under a contract awarded July 31, 1998; construction began October 23, 1998, the bridge opened to traffic on October 26, 2000, and remaining work finished April 25, 2001. The completed 200-foot single-span replica Jackson Truss covered bridge, called the Cumberland County Covered Bridge, was reported at the time to be the longest single-span timber bridge in the United States with no posted weight limit and received several national and state awards in 2001 and 2002.