The sleepy little town of Haleiwa is nestled comfortably along Oahu’s North Shore. And it feels like you’re in the country — as it’s a complete 180 from the crowds of Waikiki. Over 100 years ago – before Waikiki built its first hotel, visionary businessman Benjamin J. Dillingham opened Hawaii’s finest lodging on a small strip of land between the Pacific Ocean and the Anahulu River. He named the grand Victorian hotel Haleiwa which means the House of the Iwa – the frigate bird that, according to Dillingham, evoked the style he intended for the Haleiwa hotel. Back in the day, Haleiwa was set in the middle of nowheresville – literally. It was a day when no one worried about keeping the country country. Dillingham’s plan was to lay down a railroad through which he could serve his sugar plantations between Honolulu and Waialua. Add in a grand hotel at the end of the line and BOOOM – we’re talking bank!
For many years, it was a leisure spot “out of town” that evolved into a community which adopted the name Haleiwa. The hotel is long gone – sadly – but it’s still a hopping place! A surfer’s delight I might add. Designated a Historic, Cultural and Scenic District in 1984, Haleiwa has maintained its simple charm and laid-back environment. This is definitely a boardshort and slippah kind of place.