In the early nineteenth century there were three routes from Honolulu to Windward Oʻahu: around the island by canoe; through Kalihi Valley and over the pali by ropes and ladders; and over Nuʻuanu Pali, the easiest, quickest and most direct route.
The first foreigner to descend the Pali and record his trip was Hiram Bingham (my great-great-great grandfather.) His zeal for spreading the word of God led him to take a group of missionaries over the Pali to the Koʻolaupoko area in 1821.
The current Pali Highway is actually the third roadway to be built there. A large portion of the highway was built over the ancient Hawaiian foot paths that traversed the famous Pali pass.
In 1845 the first road was built over the Nuʻuanu Pali to connect Windward Oʻahu with Honolulu. It was jointly financed by the government and sugar planters who wanted easy access to the fertile lands on the windward side of Oʻahu. Kamehameha III and two of his attendants were the first to cross on horseback.
A legislative appropriation in 1857 facilitated road improvements that allowed the passage of carriages. The Rev. E. Corwin and Dr. G. P. Judd were the first to descend in this manner on September 12, 1861.
In 1897, Johnny Wilson and fellow Stanford student Louis Whitehouse won the bid to expand and construct a ‘carriage road’ over the Pali. Ground was broken on May 26, 1897 and the road was opened for carriages on January 19, 1898.
When the current Pali Highway and its tunnels opened (1959,) the original roadway up and over the Pali was closed and is now used by hikers.
I am old enough to have traveled (and young enough to still remember traveling) on the Old Pali Road over the Pali before the tunnels were built.
Living on the windward side and initially going to school and then in later years working in Honolulu, there was always a satisfaction of going through the tunnels and heading home, leaving the rest of the world behind you.
Folklore holds that you should never carry pork over Old Pali Highway, especially at night. Motorists reported that their cars mysteriously stopped and would not start until the pork was removed from the car.
The stories vary, but are rooted in the legendary relationship between fire goddess Pele and the demigod Kamapuaʻa (a half-man, half-pig.) The two agreed not to visit each other.
If one takes pork over the Pali, you are bringing a physical form of Kamapuaʻa into Pele’s territory and breaking their agreement. Some versions note a white dog appears when your car stalls.
The Pali was the site of the Battle of Nuʻuanu, one of the bloodiest battles in Hawaiian history, in which Kamehameha I conquered Kalanikupule of Oʻahu, bringing it under his rule.
In 1795 Kamehameha sailed from his home island of Hawaiʻi with an army of thousands of warriors, including a handful of non-Hawaiian foreigners.
The war apparently ends with some of Kalanikupule’s warriors pushed/jumping off the Pali. When the Pali Highway was being built, excavators counted approximately 800-skulls, believed to be the remains of the warriors who were defeated by Kamehameha.
If you’re driving up the Pali Highway from town you can see two notches cut in the narrow ridgeline. The notches are man-made. Many believe they were cannon emplacements, used especially during the Battle of Nuʻuanu between Oʻahu’s Kalanikupule and Hawaiʻi Island’s Kamehameha.
However, per Herb Kane, “Kalanikupule had some arms bigger than muskets, but they were probably just swivel guns. Besides, the Battle of Nu‘uanu Pali started as a skirmish by Diamond Head, and no one knew where the battle would end up. Kalanikupule could not have planned it that way.”
“Hawaiians, like everyone else, understood the value of high ground. These are certainly (pre-Cook) lookout stations, and that’s why you see them all over the islands – if you look out for them.”
Lili‘uokalani used to visit friends at their estate in Maunawili. She and her brother King David Kalākaua were regular guests and attended parties or simply came there to rest.
Guests, when leaving the home, would walk between two parallel rows of royal palms, farewells would be exchanged; then they would ride away on horseback or in their carriages.
On one trip, when leaving, Liliʻu witnessed a particularly affectionate farewell between a gentleman in her party and a lovely young girl from Maunawili.
As they rode up the Pali and into the swirling winds, she started to hum a melody weaving words into a romantic song. The Queen continued to hum and completed her song as they rode the winding trail down the valley back to Honolulu.
She put her words to music and as a result of that 1878 visit, she wrote “Aloha ‘Oe.”
The melody may have been derived from Croatian folk song (Subotika region) Sedi Mara Na Kamen Studencu (Girl On The Rock,) in 1857 published in Philadelphia by Charles Crozat Converse as The Rock Beside The Sea.
Aloha ʻOe was first introduced in America in 1883 by the Royal Hawaiian Band with Heinrich (Henry) Berger conducting.
(When Liliʻuokalani was imprisoned, Johnny Wilson’s mother Eveline (Townsend) Wilson was her lady in waiting. During her imprisonment, Queen Liliʻuokalani was denied any visitors – but Johnny would bring newspapers hidden in flowers from the Queen’s garden.)
(Reportedly, Liliʻuokalani’s famous song Kuʻu Pua I Paoakalani (written while imprisoned,) was dedicated to Wilson (it speaks of the flowers at her Waikiki home, Paoakalani.))
(The other early set of Koʻolau tunnels, first known as the Kalihi Tunnel (competed in 1960) were named in honor of Johnny Wilson. The H-3 tunnels are named after Tetsuo (Tets) Harano, a former DOT Highways administrator.)