A spring in the vicinity of Ash Hollow Cave made it an attractive site for human habitation. At least four distinct cultures spanning over 1,500 years have been revealed in archaeological explorations of Ash Hollow Cave. These include the Apache from A.D. 1675-1725; the Central Plains Tradition from A.D. 900-1450; the Woodland Tradition from A.D. 0-1100; and the Late Archaic Tradition from 1000 B.C.-A.D. 500. The cave was apparently used as a base camp for hunting and food collecting.
The site became a Nebraska state park in 1962. Ash Hollow Cave was named a National Historic Landmark in 1966, and the surrounding area was named the Ash Hollow Historic District in 1975. In 1978, a visitor center was built overlooking the canyon.
Windlass Hill is located along the Oregon-California Trail. The hill marked the entrance from the high table lands to the south into the Ash Hollow area and the North Platte River valley. Wagon ruts are visible on the hill. The name "Windlass Hill" was not used by the emigrants, and the source of the name is unknown. Emigrants had a hard time going down the hill at a 25 degree angle, going down for about 300 feet.