Kailua, on the Windward side of O‘ahu, is world-renowned for its grand mountain vistas, majestic breezes, white sandy beaches and Hawai‘i’s largest wetland, the Kawainui Marsh. Located 12 miles northeast of Honolulu over the Nu‘uanu Pali, Kailua symbolizes a balance between the present and the past in a way that locals will often describe as “uniquely Hawaiian.”
Historians and researchers can trace Kailua’s history to its settlement by ancient Polynesians some 1,700 years ago. Kailua, meaning “Two Waters,” was a natural draw for ancient Hawaiians. With its beach, bay, natural fishponds and freshwater streams flowing from the Ko‘olau mountain range, Kailua had everything a new settlement needed, it was a place for a chief and his people to live and cultivate the land.
In the 1780s, Kailua became a gathering place for the chiefs or ali‘i from throughout the island chain. Kahekili, the high chief of Maui, and his supporting chiefs settled here while conquering O‘ahu. For this reason, Kailua is considered a former capital of O‘ahu. When King Kamehameha the Great united the Hawaiian Islands in 1795, he oversaw the development of O‘ahu’s natural resources and was known to fish and work in Kawainui and Ka‘elepulu ponds in Kailua. In the 1800s, royalty, including Princess Liliuokalani, who would later become the last queen of Hawai‘i, would spend holidays in Kailua. It was on a ride from Kailua over the Pali that the princess was inspired to write her most famous musical composition, “Aloha Oe.”
Into the 20th century, Kailua remained a sleepy little beach town. It was a place for ranching, fishing and the cultivation of pineapple and rice. Up until 1940, the population was only about 1,500. Change came with World War II and Kailua experienced “boom town” growth. Harold K.L. Castle gave land to the U.S. government to expand the naval base at Kaneohe Bay. In 1942, Castle shut down his cattle operations. In 1946, Liberty House (now Macy’s) opened in Kailua Town, creating 50 jobs for a growing commercial district. The following year the first supermarket in Hawai‘i opened in Kailua. By the end of the 1950s, Kailua’s population grew to more than 24,000.
In the 1960s, Kailua was the second largest and fastest growing community in the state. With the completion of the Castle Medical Center, the Pali Highway tunnels, the relocation of Kailua High School and the opening of Hawaii Loa College, Kailua was becoming a truly livable community for families. Kailua remains a highly desirable place to live and visit on O‘ahu.