Maunalua, the traditional name for the area now known as Hawai‘i Kai, literally means two mountains in reference to Kuamo‘okāne (Koko Head) and Kohelepelepe (Koko Crater), on the east side of O‘ahu.
Numerous small valleys are contained within, and a Keahupua o Maunalua (Kuapā Fishpond) is also located on the coastline in the western portion of this ahupua‘a. (KSBE)
Before Western contact, there was a close association between the regions of Wawamalu (Sandy Beach) and Waimanalo. (Ka Iwi Master Plan)
The land of Maunalua was formerly an ‘ili (subdivision) of the Waimanalo ahupua‘a and originally belonged to Ko‘olaupoko district. (KSBE) This “would indicate an easy route of communication between the two lands.” (McAllister)
During his visit to Maunalua in 1810, John Papa ‘Īʻī noted the ancient trail system of Oʻahu and its connection to Maunalua. He wrote, “go along Keahia and so on to Maunalua, to the sea of Koko, to Makapuu, and so on”. This mention of the trail indicates that this route extended through Maunalua, continued on to Kealakīpapa Valley, and ended at Waimānalo. (Nohopapa)
“This path may have existed in 1822, when Mathison passed from Waimanalo to Maunalua, but it was not known to him. Mathison was guided by an English sailor who had settled in Waimanalo.” (McAllister)
Before Western contact, there was a close association between the regions of Wawamalu (Sandy Beach) and Waimanalo. (Ka Iwi Master Plan)
“Running from a point slightly mountainwards of the [Makapu‘u] lighthouse road up Kealakipapa Valley, down the Waimanalo gap, and through the village site in Waimanalo, are the remains of an old road.”
“It has not been definitely determined whether it is of old Hawaiian origin or of post-European construction. … The name of the valley, Kealakipapa (paved roadway), indicates that a trail at least has been here for many years.” (McAllister)
In 1851, William Webster, a land agent of the Hawaiian Kingdom, produced the earliest map of Maunalua. The map depicts a road extending from the cliff of Makapu‘u Bay to Kealakīpapa Valley, which might be the ancient trail previously mentioned by ʻĪʻī. (Nohopapa)
The name Ka Iwi is derived from the Ka Iwi Channel, which lies between the islands of Molokai and Oahu. This area of Ka Iwi can be divided into four topographic regions: a coastal zone (referred to as Queen’s Beach); a valley (Kealakīpapa Valley); a rocky headland (Makapu’u Head); and a coastal bench.
Queen’s Beach generally refers to the shoreline area from Kaloko Beach to the rock cliffs of Makapu’u Head. Kealakīpapa Valley comprises the area from Makapu’u Saddle down to Queen’s Beach.
Makapu‘u Head, rising northeast of Kealakīpapa Valley, reaches 647 feet above sea level at its highest point. Kealakīpapa Valley through to Queen’s Beach allows the viewer to see both the windward and leeward shores from this vantage point. (Ka Iwi Master Plan)
Access between the two areas was by way of the road named Kealakīpapa, which is now generally the route of Kalanianaole Highway. “An ali’i who lived at Wawamalu had the road built. He made the people who annoyed him build the road.” (Pukui, Maunalua-net) It has also been referred to as the old “King’s Highway.”
The mouth of Kealakīpapa Valley, at Queen’s Beach, is wide and narrows to its head near the Makapu’u Lookout at 160 feet. (Ka Iwi Master Plan)
“In places the natural outcroppings of rocks have been used as steps, but where stones have been laid and a terraced wall built up to support the paving, this paving has been constructed with large stones laid at an angle sometimes as great as 45 degrees. From the foot of the gap the road ran into the village site on the Waimanalo side.”
“Near the top of the gap, on the Maunalua side, is a small walled enclosure which, according to Stokes, is said to have been made at the time of the rebellion in 1895. From the top of the gap down Kealakipapa Valley for about 600 feet the road is in fairly good condition and can be followed with ease.” (McAllister)
“The central part is paved with flat stones 1 to 2 feet in width, with smaller stones heaped about a foot in height on either side, Along this distance the road averages between 15 and 16 feet in width.”
“Farther into the valley the road runs into a heavy growth of kiawe. Here it is generally without the side rock-walls, about 11 feet wide, and of arched or curved surface.”
“Throughout the lower part of the valley the road is in a poor state of preservation. On the immediate mountain side of the lighthouse road it cannot be found. Seaward of the lighthouse road it appears again and seems to end some 140 feet from the present road, for on the sea side of this point it cannot be found.” (McAllister)
“The plain below Kamiloiki and Kealakipapa was known as Ke-kula-o-Kamau[u]wai. This was the famous potato-planting place from which came the potatoes traded to ships that anchored off Hahaione in whaling days.” (Handy)
In 1859, Maunalua was included in the Kona district with the Revised Laws of Hawai‘i 1925, setting the district boundaries from Makapu‘u Head to Moanalua inclusive. (KSBE)









