The Waialua Sugar Plantation became the largest of three sugar plantations in the area and began its north shore operation in 1865 but soon failed. The plantation, sold in 1874, struggled with getting their sugar product to the steamships in Honolulu because of its remote location. The struggling plantation was sold to the large sugar corporation Castle & Cooke in 1898. They built a new mill along with a substantial surface water storage system which would produce the largest water storage capacity in the island chain. The company soon expanded its acreage and the newly built railway system, started in 1889, would extend from Honolulu to Haleiwa by 1897 enabling the transportation of sugar to Honolulu as well as passengers and freight from Honolulu.
The Oahu Railway and Land Company’s (OR&L) owner, Benjamin Dillingham, would build Hawaii’s first and finest grand Victorian resort hotel on the north shore in 1899. Dillingham named the hotel Haleiwa, which means “house of the iwa” (“iwa” is a Hawaiian frigate sea bird).
A weekend getaway to the “country” (an affectionate term for the north shore) from Honolulu to the Haleiwa Hotel cost $10 and included an overnight stay at the hotel, a carriage ride to the nearby town of Wahiawa in touring the pineapple plantation and a trip through the Waialua Sugar Plantation and its state of the art steel fabricated sugar mill. With the best water infrastructure in the islands, the north shore would sustain 10,000 acres of sugar cane production for nearly 100 years. The Waialua Plantation ceased sugar production in 1996.
Ultimately Waikiki would win the tourism battle, and the Haleiwa Hotel would shut down in 1943. However, the community that had built up around the hotel would formally take the name “Haleiwa” for itself.