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.
On Oahu’s Windward coast, the Nuʻuanu Pali lookout watches over the cliffs of the Ko’olau mountains. The Koʻolau Range is a name given to the fragmented remnant of the eastern or windward shield volcano of the Hawaiian island of Oʻahu. It was designated a National Natural Landmark in 1972, and is truly one of the best viewpoints on Oahu to gaze out across the landscape. The Pali Pass provides panoramic vistas looking out toward Chinaman’s Hat and Kāneʻohe Bay. To clarify, Kāneʻohe Bay is the largest sheltered body of water in the main Hawaiian Islands. This reef-dominated embayment constitutes a significant scenic and recreational feature along the windward (northeast) coast of the Island of Oʻahu. The largest population center on Kāneʻohe Bay is the town of Kāneʻohe.
The Pali Pass claimed its spot in Hawaiian hsitory in 1795 when it become the site of a massacre where King Kamehameha defeated the island’s warriors by forcing them off the treacherous cliff top to their deaths. Suggestion: you’ll need a tripod or be able to grip the railing because it can get extremely windy — and consider another layer of clothing because it can be chilly. Aloha.