Roughly 36,000 vehicles a day pass through the Pali Highway tunnels between Honolulu and the windward side, going by the state’s own 2024 traffic counts, and almost nobody in those vehicles is thinking about 1795. We do it too. Coffee in the cupholder, radio on, through the tunnels and out into that wall of green and wind. But the pass you just drove through is the single most consequential piece of ground in Oʻahu’s history. In May of 1795, an invading army from Hawaiʻi Island pushed the defenders of Oʻahu up this exact valley and pinned them against the cliff at the top. What happened at the edge gave the battle its Hawaiian name, and it ended Oʻahu as an independent kingdom.
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The valley was always the door to Oʻahu
Nuʻuanu Valley runs from downtown Honolulu up into the Koʻolau Range and narrows to a gap at the top. On the far side, the mountain simply stops. The land falls away in a sheer face toward Kāneʻohe and Kailua, and the trade winds funnel through that gap hard enough that people have been leaning into them for two centuries.
Long before any road, a footpath crossed here. Historic Hawaiʻi Foundation notes there is no known date for when the trail was first built, only that it predated Western contact, because this was the most direct route between windward Oʻahu and Honolulu. Farmers carried poi, sweet potato, fruit, and pigs over it to sell in town, then hauled goods back. Foreigners who saw it in the 1800s described ropes and ladders and a drop of several hundred feet, and they marveled at how easily Hawaiians moved along it.
So when we talk about an army being driven “up the valley,” understand the geography. Nuʻuanu is not an escape route. It is a funnel that ends at a cliff.
How Oʻahu got weak: 1794 and a very bad year
Kamehameha did not walk into a strong Oʻahu. He walked into one that had been tearing itself apart.
Kahekili II, the powerful chief who had ruled Maui and taken Oʻahu, died in mid-1794. His holdings split: his son Kalanikūpule took Oʻahu, while his half-brother Kaʻeokūlani held Maui, Lānaʻi, Molokaʻi, and influence on Kauaʻi. That division did not hold. Kaʻeokūlani, traveling home to Kauaʻi by way of Oʻahu, discovered his own chiefs plotting to throw him overboard, and rather than sail on he proposed war against his nephew. The fighting, known as Kukiʻiahu, ran from mid-November into December 1794 and ended near ʻAiea with Kaʻeokūlani’s army destroyed.
Kalanikūpule won that one, but only with the help of the cannons of Captain William Brown’s ships. Then came the part that really cost him. A dispute over payment turned violent, Brown and several of his men were killed, and Kalanikūpule seized the two vessels, the Jackall and the Prince Lee Boo, along with their arms. On January 4, 1795, he set sail for Hawaiʻi Island intending to attack Kamehameha directly. It fell apart at anchor off Waikīkī. The ships’ crews retook their vessels, sailed for Hawaiʻi Island, told Kamehameha everything, and traded him all the weapons Kalanikūpule had left aboard in exchange for supplies.
Sit with that for a second. In the span of a few months, Kalanikūpule fought a costly civil war, lost his foreign firepower, and personally delivered a shipment of muskets and intelligence to the man about to invade him.
The largest army the islands had ever seen
Kamehameha had begun his campaign to bring the chain under one rule in the early 1780s, after the death of Kalaniʻōpuʻu, and by early 1795 he had unified Hawaiʻi Island but nothing beyond it. That winter he assembled a force that Hawaiian accounts describe as the largest ever put together in the islands: roughly 12,000 warriors and about 1,200 canoes, numbers preserved through Samuel Kamakau’s Ruling Chiefs of Hawaiʻi and Thomas Thrum’s annuals.
The difference was not just size. Kamehameha had spent years absorbing Western weapons and, more importantly, Western gunnery discipline, with British sailor John Young and his companion Isaac Davis training crews on muskets and cannon. Both men had ended up on Hawaiʻi Island years earlier and became trusted advisors. Kalanikūpule had foreign guns too. He just had fewer of them, and fewer people who knew how to use them well, which is exactly what the seizure of Brown’s ships had cost him.
Kamehameha moved first on Maui and Molokaʻi, taking them in the early spring of 1795. Then he turned toward Oʻahu.
The landing, and the fight through Honolulu
The fleet came ashore on the southeastern side of the island, covering the beaches from Waiʻalae through Waikīkī. The landings were unopposed. Kamehameha’s forces had roughly four days to gather food and scout Kalanikūpule’s positions before moving.
Kalanikūpule had prepared. He had been warned by chiefs from Maui and Molokaʻi and had built lines of defense, with his chiefs stationed at points up the valley that Kamakau recorded by name: Kanoneakapueo, Kahapaʻakai, Luakaha, Kawānanakoa, Kaukahoku, Kapaʻeli, Kaumuʻohena, and Puʻiwa, where the fighting began. Kaʻiana, one of Kamehameha’s own chiefs, had defected. He had fallen out of favor and believed he was being plotted against, so on the voyage over his contingent split from the armada, landed on the north side of the island, and went to work cutting notches into the Nuʻuanu ridgeline to serve as gunports for Kalanikūpule’s cannons.
The armies first clashed near Punchbowl Crater. Kamehameha split his force, sending half around the crater in a flanking move while the other half pushed straight ahead, and he put his own cannons on the Papakōlea ridgeline, driving off the gun positions above him. Both sides were fighting with traditional Hawaiian weapons alongside firearms, and one detail from Stephen Desha’s account of Kamehameha and his warrior Kekūhaupiʻo deserves more attention than it usually gets: the aliʻi wahine, the female chiefs on Kamehameha’s side, were firing muskets into Kalanikūpule’s ranks from the opening of the battle. Desha writes that the warriors around them fought harder for seeing it.
Pressed from both sides, the Oʻahu forces fell back to their next line near Laʻimi, just above the land that later became Queen Emma’s summer home. There, a well-aimed shot from John Young’s cannon killed Kaʻiana. Kalanikūpule was wounded in the same phase of the fighting.
That was the hinge. With Kaʻiana dead and Kalanikūpule hurt, the Oʻahu command came apart, and what had been a defense became a running retreat with cannon fire coming down from the heights.
Kaleleakaʻanae: the leaping mullet
The name Hawaiians gave this battle is Kalelekaʻanae, also written Kaleleakeʻanae depending on the source, and it means “the leaping of the ʻanae,” the mullet. It is not a gentle name. It describes bodies going over the cliff the way mullet leap, and it refers to the Oʻahu warriors, and by some accounts members of their families, who were forced over the edge at the back of Nuʻuanu Valley or went over rather than be taken.
Be careful with the numbers here, because most retellings are not. Commonly repeated figures put several hundred at the pali, often cited as more than 700. The Hawaiian Historical Society has published cautions that Hawaiian battle-casualty data is unreliable and prone to serious exaggeration, and even the Kamehameha Schools cartographic study of the battle opens by acknowledging that the histories of Nuʻuanu are varied and sometimes conflicting. What is solid is that the toll was severe and that it happened at this cliff.
It is also worth saying plainly that not everyone died there. Accounts collected in Nuʻuanu describe defenders escaping up Pacific Heights, over Alewa into Kalihi and out toward ʻAiea, and down the old trails on the pali itself into Kāneʻohe. People got out.
Then, roughly a century later, the ground gave up its evidence. During the roadwork that cut the new carriage road over the Pali, crews at the foot of the precipice uncovered an estimated 800 skulls along with other bones, believed to be the remains of the warriors who fell in 1795. Sources differ on whether this was 1897 or 1898; the construction spanned both years, with ground broken in May 1897 and the road opened in January 1898, so either date is defensible and we would not state one as certain.
What happened after
Kalanikūpule escaped the valley. He hid in the mountains before he was captured, for months by most accounts and longer than a year by some, and Kamehameha sacrificed him to his war god Kūkaʻilimoku at Papaʻenaʻena heiau, which stood on the slope of Lēʻahi, the crater most visitors know as Diamond Head. The heiau is gone now.
Nuʻuanu was the climax of the campaign. After it, Kamehameha’s realm was referred to as the Kingdom of Hawaiʻi for the first time. But the chain still was not whole. Kauaʻi and Niʻihau remained outside his control, and two attempted crossings failed, one turned back by a storm and one halted by an epidemic that swept his forces. The resolution came without a battle: in 1810, Kaumualiʻi of Kauaʻi met Kamehameha in Honolulu and acknowledged him as supreme ruler while continuing to govern Kauaʻi himself. Historians describe that cession as more symbolic than practical, and Kaumualiʻi’s compliance was inconsistent in the years that followed. Unification was real, and it was also messier than the one-sentence version.
From footpath to freeway
The road you drive is the third crossing built here, and the sequence is worth knowing because it explains what you can and cannot see today.
In 1845, under Kamehameha III, the footpath was widened to about six feet (1.8 m) and paved with large stones for horses and carts. The king and his interior minister, Gerrit Judd, were the first to ride it. It stayed rough and genuinely dangerous for decades. A wagon was driven down it in 1861 and a buggy made it up in 1862, but by 1869 drivers were being warned off attempting the same.
The carriage road came only after the overthrow of the monarchy. In May 1897, under the Republic of Hawaiʻi, John Wilson and Louis Whitehouse won the contract at $375,000, the only bid under the appropriation. The two had met in Stanford’s engineering department. Their roadway ran 7,620 feet (about 2,320 m), built with blasting powder and dynamite, 16 feet (4.9 m) of macadam surface on a 20-foot subgrade. Wilson, Honolulu-born with Hawaiian, Tahitian, and European ancestry, went on to serve as mayor of Honolulu across nearly two decades.
By 1931, more than 2,000 cars a day were negotiating the 22 hairpin turns of the old Pali road. People had been asking for a tunnel since about 1850. The first one finally opened to one-way traffic in 1957, the second was finished in 1961, and the Pali Highway, all 11 miles (17.7 km) of it, was formally dedicated in December 1962. When the tunnels took the traffic, the old road over the top was left behind, and a stretch of it is now the paved path you can walk from the lookout.
Standing there today
The Nuʻuanu Pali State Wayside sits at about 1,200 feet (366 m) of elevation, and the drop past the railing is commonly described as around 1,000 feet (300 m). The state’s own description of the site is refreshingly blunt about the conditions: the winds are usually so strong that you can lean against them. Bring a layer. It is often 10 to 15 degrees cooler up there than in Waikīkī, and rain blows through sideways with no warning at all.
Nuʻuanu Pali State Wayside, off Nuʻuanu Pali Drive at the Pali Highway (Route 61), Kāneʻohe, HI 96744. Open daily 6:00 a.m. to 6:00 p.m. Parking is $7.00 per vehicle for non-residents and free for Hawaiʻi residents with valid ID, paid at the kiosk. Current hours, fees, and any closures are posted on the Hawaiʻi Division of State Parks page for the wayside. From Waikīkī it is about a 25-minute drive. The lot is small and fills up midday, so early morning is both quieter and clearer, since clouds tend to stack against the Koʻolau as the day warms.
Walk past the main viewing platform and you can follow the old highway pavement for a stretch. It is a short, easy walk with better views than the crowded railing, and you get the odd sensation of standing on a road that used to carry traffic and now carries nothing.
One thing we would ask. This is a burial place. However you count the dead, hundreds of people died at this cliff, and bones were recovered at its base within living memory of some families still here. Iwi kūpuna, ancestral remains, are sacred in Hawaiian culture, and the ground below the lookout is not a curiosity. Stay on the paved paths and behind the railings, which is both the respectful choice and the safe one, since the terrain past them is loose and lethal. If you see offerings left at the site, leave them alone. And skip the ti-leaf-and-pork story you will hear from someone in the parking lot; it is modern folklore, not Hawaiian tradition, and it tends to crowd out the actual history of the place, which is far more worth carrying home.
That is really the argument for stopping here. The view is the reason most people pull over, and it is a stunner. But the reason the view matters is that a kingdom ended at this railing, and the islands that came out the other side of 1795 are the islands you are standing in.
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