North Shore NewsBenjamin F. Dillingham, founder of O’ahu Railway and Land Co., opened the Hale’iwa Hotel in 1899 on forty oceanfront acres. The grand Victorian hotel was designed by architect Oliver Traphagen, who also designed Waikīkī’s 1901 Moana Hotel. Hale‘iwa Hotel enabled the railway company to earn passenger fares in addition to its bulk sugar hauling to Honolulu.
As Hawai‘i’s first destination resort, the two-story hotel included a ballroom, hunting lodge, 14 suites and four cottages with private baths, hot and cold running water, and telephones. Guests could enjoy lū‘au, canoeing, fishing, tennis, golfing, rides on a glass-bottom boat, tours of the Waialua Sugar Mill and more. Queen Lili‘uokalani stayed here when her nearby home became overcrowded.
The hotel’s popularity declined over time, prompting the hotel’s closure in 1929. It re-opened as a beach club in 1930, then as a WWII Army officers’ club, closing permanently in 1948. It was demolished in 1952. The Sea View Inn restaurant built on the site in 1955, became the Chart House in 1990, then Hale’iwa Joe’s in 1998.