Haleiwa Hotel

More than a year before Waikiki built its first grand hotel, visionary businessman Benjamin Dillingham opened a luxury resort hotel on a strip of land on Oahu’s North Shore. He called it “Haleiwa,” which had been the name of a girls’ dormitory built by Protestant missionaries in Waialua in the 1830s. But it's not hard to see the image of the ‘iwa bird itself — noted for its enormous, angular wingspan — reflected in the design of the hotel itself, with its elongated roofline, perched on a gentle mound.

Whereas the Moana and, later, the Alexander Young Hotel in downtown Honolulu served the traditional function of accommodating visitors, Dillingham’s hotel was conceived as part of a larger concept. Having built the Oahu Railway & Land Company, whose primary purpose was to provide a means of transporting sugar from western Honolulu and the North Shore to Honolulu Harbor, Dillingham hoped to capitalize on his investment by encouraging passenger travel as well, and his new hotel was a means to this end.


To entice passengers to take the three-hour, fifty-six mile rail journey from Honolulu to Haleiwa, Dillingham planned to develop luxurious accommodations situated in a deluxe country club setting as an end-of-line attraction. Leasing forty acres of land along the ocean and the Anahulu stream from Bishop Estate, the railroad magnate hired O. G. Traphagan, who was to design the Moana Hotel in 1901, to realize his grand scheme. As at the Moana, the architect responded with an elaborate Victorian layout, masterfully combining a sense of privileged grandeur and country informality.

When the hotel opened on August 5, 1899, guests were conveyed from the railway terminal over the Anahulu stream to fourteen luxurious guestrooms. Each room had a private bath, hot-and-cold running water, and telephone connection with the front desk. The resort offered a myriad of recreational activities including tennis, canoeing, ocean fishing, and golfing. There was an ocean-front nine-hole golf course, the second to be constructed in the islands, as well as a large concrete swimming pool of soft fresh water filled from the property’s springs.

The weekend getaway from Honolulu to the Haleiwa Hotel became hugely popular with the Island’s affluent. At the turn of the century, a round-trip, two-day excursion by train cost $10. It included an overnight stay at the hotel and a tour of the Waialua Sugar Mill (Dillingham was director of the Waialua Sugar Company). From there, visitors took a carriage ride to Wahiawa to view the pineapple plantations (Dillingham founded Hawaiian Pineapple in 1901). In effect, it was a trip through “Dillingham World.”

Ultimately however, even Dillingham could not resist the gravitational pull of Waikiki as the focus of the tourist industry. This was due in part to the newly aggressive promotion of tourism by the Honolulu Merchants’ Association and the opening in 1927 of the Royal Hawaiian Hotel, which instantly provided Waikiki with a hotel of worldwide distinction.

The territorial government then stepped in with two critical projects which led to private sector capital investments. The first was the construction of the Ala Wai Canal (1920-1928). The government also upgraded the harbor’s visitor reception facilities — piers 8, 9 and 10 were rebuilt between 1920 and 1924 and construction of the Aloha Tower was completed in 1926.

The Matson Navigation Company also advanced the government’s tourist agenda with the launching of the 17,000-ton Malolo in 1925. The 650-passenger luxury oceanliner was the fastest ship on the Pacific at the time, reducing the six-and-a-half day journey from San Francisco to four-and-a-half.

During the height of its popularity, the Haleiwa Hotel had made the name Haleiwa famous, and when its doors closed in 1943, its name was adopted by the surrounding community. About 1953, the aged, termite-ridden structure was torn down. Haleiwa Joe’s restaurant now stands on the site where the ‘iwa once soared.