Thousands of years ago, around 500 A.D., it was believed that ancient Hawaiians resided in Kailua, mostly on the slopes around the Kawainui Marsh. The archeological evidences in the marshland are proofs that the first Hawaiian residents of Kailua used to live beside a cove and fished because the topography is not suitable for land tilling.
Kailua is also a mother of many legends. Written and told stories that are kept in Hawaiian State Libraries can attest that. These include the menehune who are evening workers in Kaiwainui Marsh and mo’o which seems to be a giant lizard that attracts fishes.
Before Captain Cook came, Kailua had a considerably big population and used to be the capital of O’ahu’s kings. This place became known when King Kamehameha I dominated O’ahu and made Hawaiian Islands unite. Subsequently, Kaiwainui Marsh, the old Kailua, and the freshwater and saltwater ponds at Mokapu were rewarded to the fighters and chiefs who were part of the King’s quest. And instead of continuing the fishing in the place, they cultivated the land with crops like sugarcane, rice, and taro. They also used it for cattle raising.
In the 1940s, Kailua’s appearance became far from its ancient landscapes. From Kaneohe Ranch’s agricultural land, parts of it became the Navy base and the Army’s Fort Hase. It was the time when the government needs to put up structures for the military because of World War II. The owner of the ranch Harold K.L. Castle donated the land for post-war development.
In the late 1950s, Kailua started to recover from the injury of World War II and became urbanized. A highway that tunnels through the Ko’olau Mountains was built and commercial shops like a small Liberty House (now Macy’s) opened, commissioning three employees. It was upgraded to a department store in 1953 with 17 times more than its original number of employees. Kailua also pioneered the first bowling alley, a telephone company branch office, and the first supermarket in Hawaii, which became a state by the end of 1950s. Kailua, at that time, became the official postal destination. By 1992, the town’s population grew from 24,402 (1960) to 50,000 residents.