In the late 18th century, there were two roads over the Shenandoah Mountains between Alexandria and Winchester, crossing the Shenandoahs at Snickers Gap (now along State Route 7) and Keys Gap (State Route 9). The Virginia General Assembly, in 1785, passed a law appointing nine commissioners (a non-profit turnpike trust) and instructing them "to erect, or cause to be set up and erected, one or more gates or turnpikes across the roads, or any of them, leading into the town of Alexandria from Snigger's [Snickers] and Vesta's [Keys] Gaps". This was not the first law authorizing a toll road in the United States, but was the first recorded turnpike in operation, opening by the end of 1786. Thomas Jefferson, who was at least a moral backer of the enterprise, pronounced it a success. A 1793 for sale advertisement referred to one of the two roads as "the Turnpike Road, down which all the wheat, from an extensive and fertile Country, intended for the Alexandria Market, is conveyed".
However, the lack of maintenance caused by low tolls led to the wearing out of the southern route. The Little River Turnpike, a private corporation chartered in 1802, realigned and improved the portion between Alexandria and Aldie. A similar charter for the northern route east of Leesburg was assigned to the Leesburg Turnpike in 1809, and in 1810 the Snicker's Gap Turnpike Company obtained a charter for the road from Aldie northwest over Snickers Gap and beyond to the Shenandoah River at Snicker's Ferry. (The Berryville Turnpike later improved the road beyond the Shenandoah to Winchester.) When completed, the turnpike had three toll gates over a distance of about 17.5 miles (28 km).
The turnpike company continued to operate - at least over the gap - as late as 1915, and the road later became part of the state highway system - State Route 7 over the Shenandoah Mountains west of Bluemont, and secondary State Route 734 between Bluemont and Aldie. The state had plans to transfer SR 734 to the primary system as part of State Route 234, renumbering the short State Route 245 spurring off SR 7 at Bluemont as a portion of SR 234 in the 1940 renumbering, but instead transferred this short stub (Clayton Hall Road) to the secondary system in 1943 due to low traffic.
The Virginia Department of Transportation temporarily closed the bridge on May 24, 2007 for a more than nine month rebuilding. The deteriorated mortar, and some of the stones, are being replaced, and the approaches are being rebuilt, but the bridge will remain in its original state.