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Modern-day surfing on the North Shore began in the early 40s, but Hawaiian legend tells of surfers centuries earlier.
Hawaiians settled in the Waialua and Ko'olauloa Districts along the North Shore around 1100 AD and established villages along valleys, streams, and bays. Drawn to the area by the rich ocean waters and fertile lands dotted with natural springs, they grew taro and sweet potato. Oahu and the North Shore region became home to ancient Hawaiian communities that thrived at ocean/land/river junctures such as the Anahulu River and Waimea Valley. In ancient times, the Hawaiians divided land into ahupua'a – natural divisions from the mountains, through river valleys, to the sea that contained everything necessary for sustaining life.
In 1832, Christian missionaries came to Waialua District and built a mission and girls seminary in Hale'iwa. The town was expanded by wealthy businessman Benjamin J. Dillingham at the end of the 19th century when he built the Hale'iwa Hotel.
Prior to the close of the 11th century, the ahupua'a of Waimea was given to the kahuna (priest) of O'ahu by Kamapua'a, O'ahu's ruling chief of the time. Waimea Valley remained home to the High Priest of O'ahu for over 600 years. The last was Hewahewa – the Kahuna nui under the reign of Kamehameha I. After the death of Kamehameha I, leadership of the Islands fell into the hands of Ka'ahumanu, the third of Kamehameha's wives. Together, Ka'ahumanu and Hewahewa brought an end to the ancient kapu system of Hawaii (system of laws based upon taboos, particular prohibitions, sacred ways and multiple gods). Hewahewa retired to Waimea Valley.
The first Westerners to land on O'ahu came ashore at Waimea Bay in 1779, aboard Captain Cook's ship and briefly anchored to replenish fresh water supplies after Cook's death on the Big Island. The crew recorded that the area around Waimea River was “well cultivated and full of villages and the face of the country is uncommonly beautiful and picturesque”.
The first Western settlement came in 1832, when Protestant missionaries Reverend John and Ursula Emerson, arrived in the Waialua District. Aboard the Thaddeus, the Emersons put in at Waialua Bay at the mouth of the Anahulu River, where the Anahulu (or Hale'iwa) Bridge is found today. They went on to establish Emerson House and a Protestant church in the heart of the village and Hewahewa became a regular visitor to the church. Today, that church is known as the Queen Liliu'okalani Protestant Church, named after Hawaii's last queen who vacationed in Hale'iwa at the royal summer home and worshiped at the church. It is located on Main Street in Haleiwa.
In 1837 with the death of Hewahewa, whose bones remain at Waimea Valley, the rule of the kahuna nui (most high priest) came to a close. In the mid-1800s, the ancient kahuna land system was overthrown in a great land division known as the ‘Great Mahele'.
The western system of land titles and deeds signaled the start of private land ownership, but not before Hewahewa's granddaughter, Paalua, successfully claimed one-half of Waimea Valley lands. With private ownership came the sugar cane and pineapple plantations, which dominated the economy for 100 years. Pineapple and diversified agriculture continue along the North Shore today.
In 1898, visionary businessman Benjamin Dillingham – a promoter of real estate and railways, opened Hawai'i's finest hotel. It was a grand Victorian hotel he name the “Hale'iwa”, which means “house of the ‘iwa”, or frigate bird, and was situated where ‘Hale'iwa Joe's' restaurant stands today. Dillingham felt the frigate bird best exemplified the ambience he wanted to create for the hotel. Seemingly in the middle of nowhere, the Haleiwa hotel was part of a bigger plan for Dillingham. It rested at the end of the line of his railroad that serviced the sugar plantations and enabled him to further capitalize on his investment. Dillingham was also the director of Waialua Sugar Co.