E komo mai!

The headline of a 1953 advertisement lured would-be homebuyers to a growing Kailua community with the promise of “City Living, Country Style.” Though hardly a city, Kailua today is a vibrant, self-sufficient town with an unpretentious lifestyle that has kept its appeal through the decades. Home to many, daytime destination for others, Kailua Town has managed to grow sensibly without losing sight of its rich history and unique sense of place.

The History and Growth of Kailua

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.

The Rise of ‘Modern’ Kailua

A businessman with a keen sense of community, Harold Castle pursued his vision for Kailua at the end of the war. Still considered ‘country’, he saw Kailua as a new Honolulu suburb that would help meet the post-war housing demand. Having ceased its cattle operations in 1942, Kaneohe Ranch lands were ripe for new homes and commercial development.

Kaneohe Ranch launched a major marketing campaign in the early 1950s to lure families to the Windward side. The promise of a new four-lane, two-tunnel Pali Highway helped, too. The ranch had sold its land at Mokapu peninsula to the U.S. Navy in 1943 for the establishment of what is now Marine Corps Base Hawaii and, always a generous philanthropist, Harold Castle donated many of his other land holdings – or sold them below market value – for new schools, churches and a much-needed hospital.

Sustaining long-term growth for Kailua was an important part of Harold’s vision. Residential subdivisions blossomed on former ranch and farm lands; mom-and-pop stores and roadside fruit stands were replaced by commercial enterprises in the growing town of Kailua; and within a decade ‘sleepy’ Kailua became Hawaii’s fastest growing community, with its population growing from about 7,700 in 1950 to more than 25,000 by 1960.

Kaneohe Ranch remained the largest landowner and developer in Kailua until December 2013, when Alexander & Baldwin, another kama‘aina company with a long history of community-building in Hawaii, purchased substantial land holdings from Kaneohe Ranch and the Harold K.L. Castle Foundation. They included 50 acres of commercial property, mostly in Kailua, as well as 76 acres of agriculture-zoned land and 509 acres of preservation-zoned land, also in Kailua. A&B is committed to partnering with the community to meet the changing needs of its residents and businesses and to maintain the long-term livability, desirability and beauty of Kailua Town.

Lifestyle & Culture

Driving through Kailua Town, one can’t help but be charmed by its casual, beach town environment. But beneath its laid-back façade, Kailua is an active community in every sense. Whether it’s an early morning workout along Kailua Town’s network of bike and jogging paths, an afternoon paddling practice across Kailua Bay, or just soaking up the sun and salt water with the kids in tow, folks are always out and about taking advantage of the natural beauty that surrounds this Windward Oahu destination.

It is also a community that is actively involved in preserving its heritage and shaping its future. Residents and businesses are engaged in beautification and preservation projects, coaching youth sports teams, supporting local fundraisers, and organizing the many events that have become Kailua traditions. Kailua Town’s annual Christmas light displays, farmers markets, outdoor concerts and plays, and the perennially popular “I Love Kailua” Town Party are among the activities that bring this community together in service or celebration. Kailua is a place where neighbors know each other and where you are almost guaranteed to run into a friend in a grocery store aisle or in line at the post office.