The route drew settlers who formed villages in the area and populated Nuʻuanu Valley for a thousand years.

In 1795 Kamehameha I sailed from his home island of Hawaiʻi with an army of 10,000 warriors, including a handful of non-Hawaiian foreigners.

In 1898, as this road was developed into a highway, workers found 800 human skulls—believed to be the remains of the warriors who fell to their deaths from the cliff above.

[citation needed] The trail to Nuʻuanu began at Kalanikahua and led north of Kaumakapili Church to below the stream which flowed out of Kamanuwai pond.

[11] Two large stones near the back of Nuʻuanu Valley, Hapuʻu and Ka-lae-hau-ola, were said to represent a pair of goddesses who were guardians of the passage down the pali.

Travellers would leave offerings of flowers or kapa (bark cloth) to ensure a safe trip, and parents buried the umbilical cords of newborns under the stones as a protection against evil.

[12] According to legend, the pass is inhabited by a moʻo wahine, a lizard who takes the form of a beautiful woman and leads male travelers to their deaths off the cliff, similar to a western poltergeist or mermaid.

'The Pali', together with surrounding areas such as Tantalus Crater, is the main setting in the novel Micro by Michael Crichton and Richard Preston.