In 1888, Ben Dillingham had a problem. He had built Oahu’s first railroad to haul sugar cane from the North Shore into town, but his trains returned to the “country” empty … Dillingham had no return load. He solved his problem by building a modern, Victorian-style, 40 room hotel on the North Shore, opening in 1899. Now his trains carried well-to-do “townies” and mainland visitors on their return from Honolulu. His “Haleiwa Hotel” featured a dramatic
staircase to the second floor, scenic ocean and mauka views, in-suite telephones and electric lighting, separate private cottages, shooting opportunity at a “Men’s Lodge,” boating tours, and a billiards room. A stable allowed horseback tours of the nearby sugar mill. Later, a 9-hole golf course was added. It was the first of Oahu’s premier hotels: the Moana in Waikiki opened a year later, the Royal Hawaiian not until 1927.

Over time the Haleiwa Hotel lost its battle with newer hotels in Waikiki. It became a private beach club, then an Army officer’s recreation center during World War II. It was demolished in 1952, but not before giving its name to Haleiwa Town, the picturesque plantation town that grew up around it.

A few years ago, Andy Anderson, a local entrepreneur and developer, pursued his dream of recreating a replica of the original Haleiwa Hotel. It was to be his last, best project, his gift to the North Shore. He purchased the Jameson’s Restaurant building across from Haleiwa Beach Park and drew up architectural plans for a new Haleiwa Hotel on that site. And … his plans generated local opposition. Some residents opposed any “Waikiki look-alike” in the country … never mind that Anderson was only contemplating 40-odd rooms, with the original architecture. Other
locals viewed a resurgent Haleiwa Hotel as a great idea, so controversy grew. As prospects for Anderson’s hotel at the Jameson’s property dimmed, he changed plans. He rebuilt the Jameson’s building and opened his Beach House restaurant, a classy, beautiful addition to the North Shore that has taken its place alongside other local first-rate eateries like Haleiwa Joe’s, Roy’s, and Lei Lei’s.

… and Andy Anderson made one more try. He transferred his planned Haleiwa Hotel to an oceanfront site between Haleiwa Beach Park and Pua’ena Point. Surely this out-of-the-way location wouldn’t offend the local community. Except … Kamehameha Schools, owner of Anderson’s proposed site, declined a proposed lease or sale. After nearly a year’s encouragement to Anderson, Kamehameha Schools determined that the proposed hotel location contained
probable historically significant sites and/or other impediments to development. This assessment was made in spite of an exhaustive archeological study showing no such evidence, probably because the location had been graded years earlier to locate a World War II airstrip. Regardless, as Anderson told me, “Kamehameha Schools owns the land
and is free to determine its ultimate use, which they did. Damn!”

So Anderson’s dream has dimmed, and the North Shore has missed an opportunity to recreate an architectural and historical North Shore icon and gem. It’s just too damned bad.