Kailua, on the Windward side of O‘ahu, is world renowned for its grand mountain vistas, majestic breezes, white sandy beaches and Hawaii’s largest wetlands, 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 to settle. With its beach, bay, natural fishponds and fresh water streams flowing from the Ko‘olau mountain range, Kailua had all the necessary tools for a chief and his people to live and cultivate land.

Kailua was also a place for the chiefs or ali‘i. Kahekili, the high chief of Maui, and his supporting chiefs settled here while conquering O‘ahu in the 1780s. For this reason, Kailua is considered a former capital of O‘ahu. When King Kamehameha the Great united the Hawaiian Islands in 1795, he promoted the development of O‘ahu’s natural resources, and was known to fish and work in Kawainui and Ka‘elepulu ponds in Kailua. Later into the 19th century, royalty would frequent Kailua for holiday, including Princess Liliuokalani who would later become the last Queen of Hawai‘i. It was on the ride home over the Pali that inspired the Princess 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 would generally hover around 1,500. However, World War II changed everything and promoted “boom town” growth for Kailua. Harold K.L. Castle gave land to the government to expand the Naval Base on Kaneohe Bay. In 1942, he shut down operation of 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 very first supermarket in Hawaii opened in town. By the end of the 1950s, with the completion of the four-lane Pali Highway bringing visitors and future Kailuans from Honolulu, Kailua’s population grew to over 24,000.

Into the 1960s, Kailua was the second largest community and the fastest growing community in the state. Towards the end of the decade, with the completion of the Castle Medical Center, the pending tunnels on the Pali Highway, the relocation of Kailua High School and the opening of Hawaii Loa College, Kailua was becoming a truly livable community for families. Since then, Kailua has remained a highly desirable place to live and visit on O’ahu.