The Giles, Fayette & Kanawha Turnpike was constructed as Virginia worked during the first half of the 19th century to improve transportation facilities in the western portion of the state. On March 1, 1837, the Virginia General Assembly passed legislation for the formation of the Giles, Fayette & Kanawha Turnpike Company. The goal of the company was to build a turnpike with a roadway width of 15 feet, "suitable for the passage of wagons and other wheeled carriages," from Pearisburg to Gauley Bridge.

Begun in 1838, the Giles, Fayette & Kanawha Turnpike was completed in 1848. Starting at Pearisburg, in Giles County, Virginia, it ran through Red Sulphur Springs, Pack's Ferry (near present Hinton), Raleigh Court House (present Beckley), and Fayetteville. Then it crossed Cotton Hill and New River, joining the James River & Kanawha Turnpike (present U.S. 60) at Kanawha Falls near Gauley Bridge. At a point near Fayetteville a separate road, the "Old State Road," which ran from Lewisburg and crossed the New River at Sewell, joined the Giles, Fayette & Kanawha Turnpike and continued with it to the Kanawha Turnpike.

The turnpike was valuable as a trade route and important because of its strategic value during the Civil War. Traveled by both Union and Confederate troops during the war, the turnpike took on particular significance in September 1862. On September 1, Confederate Gen. William W. Loring, following the orders of Robert E. Lee, left Pearisburg and moved up the turnpike with 4,000 soldiers. On September 10, Loring attacked federal troops at Fayetteville under the command of Gen. Joseph Lightburn. Lightburn was routed by the Confederates and eventually retreated to Charleston.

Like many early turnpikes, the Giles, Fayette & Kanawha was overtaken by the railroads in the late 19th century, becoming less important as a freight-hauling route. Portions of the old turnpike route were reused when roads were upgraded for motorized traffic in the early 20th century. In Fayetteville, a portion of the old turnpike is present State Route 16, which runs north and south of U.S. 19.