The trail was started in 1969 by the Sempervirens Fund of Conservation Associates of the Sierra Club and was extended to the Pacific by 1978 with the acquisition of the Hoover Ranch near Waddell Beach.

[1] Planning began in 1968,[2] with the initial trail segment to follow the state-controlled right-of-way along SR 9, linking Saratoga Gap to Big Basin.

[8] Prior to the expansion of Big Basin, individual permission was required to follow the trail to the sea over private lands.

[9] The Sempervirens Fund launched a new project in 1979 to acquire an additional 45 acres (18 ha) of land for the trail, with the goal of relocating it further away from SR 9.

[10] After the August 2020 CZU Lightning Complex fires, the trail closed, along with much of Big Basin Redwoods State Park.

[14] However, many hikers actually begin further southeast at Castle Rock due to its overnight parking facility; starting from Castle Rock, hikers first use the Saratoga Gap Trail, then the Travertine Springs Trail, joining Skyline-to-the-Sea at Beekhuis Road; this adds approximately 3 mi (4.8 km) to the total hiking distance.