It’s easy to understand why early Hawaiians settled in the windward Oahu district of Kailua. The ahupua‘a was blessed with fertile, stream-fed lands, cooling breezes, two natural ponds – Kaelepulu and Kawainui – and a plentiful source of food from pristine Kailua Bay. Scientific evidence has found that humans first occupied the Kailua area as early as 500 AD. However, it wasn’t until around 1200 that widespread cultivation took root here, with Hawaiians growing taro as well as bananas, sweet potato and other native crops in a vast network of terraced parcels that extended into the foothills and valleys of the Koolau Mountains.
Kailua’s bountiful resources and pleasant climate made it an attractive home for high chiefs and, later, a welcome stop for Hawaiian royalty as they traveled around the island. Life in Kailua revolved around fishing and agriculture into the early 20th century, although by the mid-1800s, the dominance of taro farming gave way to rice cultivation as Hawaii’s growing sugar industry brought Chinese immigrant workers to the Islands. When the workers’ contracts expired, many moved to Kailua and took up rice farming and milling. At one time there were as many as five rice mills in the district. By 1910, rice cultivation had waned as market demand declined.
A change in immigration laws stopped the flow of Chinese laborers to Hawaii, and Hawaii’s rice exports faced competition from growers in Texas and California. Dairy farms had begun to replace Kailua’s rice farms and became more widespread as the population grew. Also by the early 1900s, Kailua was seeing the first signs of commerce, including three Chinese-owned grocery stores located in the Maunawili area, followed by a poi factory, blacksmith, barbershop, tailor shop and other small businesses. Traveling vendors, selling housewares and sundries as well as perishables, made frequent visits to the Windward side.
Around the same time, Kaneohe Ranch Company, founded in 1893 and later acquired by James B. Castle and his son Harold Kainalu Long Castle, was accumulating large tracts of land in Windward Oahu for its ranching activities, owning some 12,000 acres from Kailua to Kaneohe. Considered one of the founding families of ‘modern’ Kailua, the Castles were the dominant land-owners in the region, holding an estimated 80 percent of the property in Kailua by the time World War II broke out.