About 6,000 years ago and before the arrival of the Hawaiians, Kawainui (the large [flow of] fresh water) and Ka‘elepulu (the moist blackness) were bays connected to the ocean and extended a mile inland of the present coastline (as indicated by inland deposits of sand and coral.)
A sand bar began forming across Kawainui Bay around 2,500 years ago creating Kawainui Lagoon filled with coral, fish and shellfish. The Hawaiians probably first settled along the fringes of this lagoon. Gradually, erosion of the hillsides surrounding Kawainui began to fill in the lagoon with sediments.
About 500 years ago, early Hawaiians maintained a freshwater fishpond in Kawainui; the fishpond was surrounded on all sides by a system of ʻauwai (canals) bringing water from Maunawili Stream (winding/twisted mountain) and springs to walled taro lo‘i (irrigated fields.)
In 1750, Kailua (two seas (probably two currents)) was the Royal Center of power for the district of Koʻolaupoko and a favored place of the O‘ahu chiefs for its abundance of fish and good canoe landings (and probably enjoyed the surf, as well.) Kawainui was once the largest cultivated freshwater fishpond on Oʻahu.
Farmers grew kalo (taro) in the irrigated lo‘i along the streams from Maunawili and along the edges of the fishponds. Crops of dryland kalo, banana, sweet potato and sugarcane marked the fringes of the marsh. Fishermen harvested fish from the fishponds and the sea.
In 1845 the first road was built over the Nuʻuanu Pali (cool height – cliff) 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.
(In 1898 this road was developed into a highway and was later replaced by the Pali Highway. When the current Pali Highway and its tunnels opened (1959,) the original roadway was closed and is now used by hikers.)
Lili‘uokalani wrote “Aloha ‘Oe” (farewell to thee) after an 1878 visit to an estate in Maunawili. She and her brother King David Kalākaua were regular guests and attended parties or simply came there to rest. Guests would walk between two parallel rows of royal palms, farewells would be exchanged; then, they would ride away on horseback or in their carriages.
In the 1880s, Chinese farmers converted the Kawainui taro fields to rice; they later abandoned their farms by 1920. Cattle grazed throughout much of Kawainui. The marsh drains into the ocean at the north end of Kailua Beach through Kawainui Canal (Oneawa Channel – built in the late-1940s.)
In 1923, planning began for the Coconut Grove subdivision. That year, Elsie’s Store, the site of the existing Kalapawai Market (the rippling water or the shining water,) opened for business. Lanikai Store (heavenly sea,) currently Kailua Beach Center, was across the street. (Kāneʻohe Ranch)
Shortly after that, Kailua’s first real estate subdivision was built, called Lanikai Crescent. In 1926, Kailua Country Club opened; it was later named Mid-Pacific Country Club. (Kāneʻohe Ranch)
In 1939, the Oʻahu Jockey Club built the Kailua Race Track – the place was nicknamed the ‘Pineapple Derby.’ In a day and age when Seabiscuit and War Admiral were stealing continental sports headlines, more than 6,000 fans turned out for 10 races at the brand new Kailua Race Track. (Hogue, MidWeek) Races reportedly continued there into 1952.
It’s not clear when it opened, but in the 1940s and ‘50s, there is clear evidence of the “Kailua Airport” (apparently, gravel/grass runway) – where ʻAikahi Park is situated today (reportedly, privately-owned and operated by Bob Whittinghill.) (When work was started in 1948 on the new airport in Kailua, Kona, to avoid confusion with the Kailua Airport on Oʻahu, the Big Island’s airport was named “Kona Airport.”)
The 1950s saw expanded development and growing population in Kailua. Kāneʻohe Ranch Company, Paul Trousdale and Hawaiian Housing Corporation joined together with several housing developments, including developments in ʻAikahi (to eat all,) Kaimalino (calm or peaceful sea,) Kalāheo (the proud day,) Mōkapu (sacred district,) Olomana (forked hill) and Pōhakupu (growing rock.) (Kāneʻohe Ranch) Kailua's population growth took a giant leap from 1,540 (in 1940,) to 7,740 (in 1950) - then another giant leap to over 25,600 people in 1960.
Homes were generally priced from $9,250 to $13,500. The first increment of homes in the Kalāheo subdivision, built by QC Lum, was selling for $9,250 on lots of 7,500-square feet. The annual land lease was $125, regardless of size. Later developments in Olomana, Pōhakupu and Kūkanono (stand strike) were priced at about $17,000. (Windward Rotary) The Pali Golf Course opened in 1953.
The first traffic signal in Kailua was installed at the intersection of Kuʻulei and Kailua Roads in 1954. That year, Foodland opened Windward Oʻahu’s first modern supermarket across from Kailua Beach Park. A couple years later (1957,) Times Supermarket opened in the new Kailua Shopping Center. (Kāneʻohe Ranch)
In 1956, the YMCA moved from its log cabin in Coconut Groove to the present site on Kailua Road. In 1957, Kailua High School graduated its first class. Prior to this time, mail delivery was directed to ‘Lanikai;’ at the end of the decade, the post office name was changed to Kailua.
Other subdivisions were developed at ʻAikahi Park, Keolu Hills (pleasant,) Olomana and Maunawili Estates. Homes in ʻAikahi Park sold for about $25,000. Shopping centers sprouted in ʻAikahi Park and Enchanted Lake to serve the incoming residents. (Windward Rotary)
Harold KL Castle donated land and Hawaiʻi Loa College (now known as Hawaiʻi Pacific University) opened in 1962. The SH Kress building was built near Liberty House (now Macy’s) in 1962, then closed its doors after a few years, and Long's Drug later occupied the building.
In 1963, after another Castle land donation, Castle Hospital opened its doors. That year, Kailua High School moved into its own campus (its present site,) having separated from what is now only Kailua Intermediate School.
In 1964, Kailua Professional Center erected the first “high-rise” (six-story) building in Kailua. It was followed shortly by the 10-story Meridian East apartment building across the street. Campos Dairy farms gave way to apartment complexes and Holiday Mart (soon to be Target) in the late-1960s.
By the end of the 1970s, Kailua opened its community center with tennis courts and a swimming pool. Thaliana Hotel, later Pali Palms Hotel (1957-1980) gave way to the Pali Palms Professional Plaza.
From 1960 to 1970, Kailua's population grew from 25,600 to almost 33,800. After that, growth was comparatively slow; the 2010 Census estimate Kailua's population at just over 38,600.
Today is Lani-Kailua Outdoor Circle’s “I Love Kailua” Town Party held in the center of town. All of the proceeds from the "I Love Kailua" Town Party pay for major plantings in Kailua and their upkeep. (Come see how the town has changed … and stayed the same.)
The image shows Kailua in 1937 – Kailua-Kuʻulei-Oneawa intersection (note small banyan tree in island where Kailua Road turns to the right (Machado.)) (Lots of information here from Kāneʻohe Ranch and Windward Rotary historical summaries.) In addition, I have included other related images in a folder of like name in the Photos section on my Facebook and Google+ pages.
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