Very few people lived there, but that shouldn’t suggest the place was without activity.
By the time of first contact with Europeans, the downtown area of Honolulu, known then as Kou, was comprised of shoreward fishponds and taro lo‘i fed by streams extending into the Nu‘uanu and Pauoa valleys.
On the opposite side (ʻEwa) of Nu‘uanu stream was a fishpond, identified as “Kawa” or the “King’s fish pond.” Iwilei at that time was a small, narrow peninsula, less populated than the Honolulu-side of Nuʻuanu stream.
Offshore from Iwilei was a small island on the coral reef on the west site of the bay. On the island was a small hut referred to as “Ka-moku-‘akulikuli” or “Kaha-ka-‘au-lana” (the early names for it were “Quarantine Island,” then “Sand Island” – it was a lot smaller, then, too.)
The first wharf at Honolulu Harbor was just north of Nuʻuanu Street. It was constructed from an old hulk sunk at the spot in 1825. This was replaced and expanded in 1837.
On the shoreline (at about what is now the intersection of Queen and Nimitz) Fort Kekuanohu was constructed. Its original purpose was to protect Honolulu by keeping enemy or otherwise undesirable ships out. Later, it was used as a prison.
In 1852, the legislature adopted a resolution directing the minister of the interior to remove the Fort and to use the material obtained thereby “in the construction of prisons, and the filling up of the reef.”
The Fort, being used as a prison, could not be removed until a new prison was built; construction for the new prison began in 1855, but not entirely completed until more than two years later. The Fort was then removed in 1857. (Kuykendall)
The Prison was on a marshy no-man’s land almost completely cut off from the main island by two immense fishponds. The causeway road (initially called “Prison Road,” later “Iwilei Street”) split Kawa Pond into Kawa and Kūwili fishponds.
Sometimes called the “Oʻahu Prison,” “King’s Prison,” “Kawa Prison” or, simply, “The Reef,” it was a coral block fortress built upon coral fill at the end of a coral built road over the coral reefs and mudflats of Iwilei.
In 1886, Mark Twain visited the prison and wrote: “… we presently arrived at a massive coral edifice which I took for a fortress at first, but found out directly that it was the government prison. A soldier at the great gate admitted us without further authority than my countenance, and I supposed he thought he was paying me a handsome compliment when he did so; and so did I until I reflected that the place was a penitentiary”.
The Prison was later relocated to Kalihi (1916) and renamed O‘ahu Jail; this is now known as O‘ahu Community Correctional Facility.
Another Iwilei activity included a railway station. In 1889, a group of businessmen led by Benjamin Dillingham founded the O‘ahu Railway and Land Company (OR&L).
OR&L built Honolulu’s first depot between Kūwili fishpond and King Street, west of Iwilei Street. The July 27, 1889 Advertiser noted, “Plans have been approved by which the main depot will be placed 180 feet from King Street in what is now a fishpond dividing Oahu Prison from the royal stables. A large portion, if not all, of this extensive fishpond will be filled in without delay…”
The railroad carried sugarcane from the plantations to Iwilei – it carried people, too. To accommodate this, the marshes and fishponds were filled in and new wharfs built. By 1901, the OR&L and other business interests had created about 500 acres of waterfront land. The docks could accommodate over 20 deepwater sailing vessels, unloading coal and loading sugar.
The last of the activities at early Iwilei was the business of sex. (Before there was Hotel Street (the 1940s gathering place,) there was Iwilei.) They called it the ‘Iwilei Stockade.’
Inside a high stockade wall were long rows of rooms, each 8×10; there were 225 of them. Most of the women were from Japan. From 4 pm to 2 am, the stockade gates were open. (Gallagher)
These women did not live at Iwilei; they only went there in the evenings, and then returned to their uptown homes at night. Some had homes of their own, others were servants of families; but all went back to town. They were in no sense isolated; Iwilei was not their home; they neither eat nor sleep there. (Special Legislative Committee Report, 1905)
Local law enforcement condoned and controlled the activities, under the guise that it was “a public necessity.” “The whole of Iwilei makai of the Oʻahu Prison has been used for the purpose of prostitution for some time past.” (Special Legislative Committee Report, 1905)
“The High Sheriff of the Territory, through his agents, has ordered all of such women (prostitutes) that are found in different parts of the City, and also in some portions of Iwilei, to move to one particular part as follows: on the makai side of Iwilei rice mill, and on the Ewa side of the Iwilei road.” (Special Legislative Committee Report, 1905)
The Iwilei brothels (or “boogie houses,” as they were also called back then) were later forced to relocate to Hotel Street and a few adjoining parts of Chinatown. By 1916, the Iwilei Stockade was shut down.
It has been suggested that one of the former Iwilei prostitutes became the role model for the key character in the silent film “Sadie Thompson,” based on W. Somerset Maugham’s short story “Rain” (as well as other adaptations.)
As time went on, more of the fringing reefs were filled, which made way for expanded commercial use. By the 1920s, small and large businesses moved in – and, now, gone are the Prisoners, Pullmans and Prostitutes from Iwilei.