North Shore, Oahu

Haleiwa

Looking back, it’s difficult to envision Haleiwa as a sparkling resort area.

This sleepy little town, nestled comfortably along Oahu’s North Shore, is a complete 180-degree turn from the hustle and bustle of Waikiki. More than a century ago, however, 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 “House of the Iwa.” The graceful frigate bird, he said, best exemplified the ambience he wanted to create for the hotel.

While the Haleiwa was set in the middle of nowhere, Dillingham had a plan. He had laid tracks for an ambitious railroad to serve his sugar plantations between Honolulu and Waialua, and he figured placing a grand hotel at the end of the line would be a way to further capitalize on his investment. For years, visitors and residents alike rode the train to spend some leisure time at the beachside resort. Shortly after, the town adopted the name Haleiwa.

The hotel is gone now, but this old plantation town continues to welcome visitors. Designated a Historic, Cultural and Scenic District in 1984, Haleiwa has maintained its simple charm and laid-back environment. Aging storefronts line its main street. This is definitely a “shorts and slippers” kind of place.

Things To Do

Exploring Haleiwa

People line up to get a shave ice at Matsumoto Shave Ice

Still, there is much to see here. Haleiwa offers a nice selection of art galleries, surf shops and eateries. Visit the North Shore Surf & Cultural Museum, established in 1999, located at the North Shore Marketplace. The museum features a wide range of surfing memorabilia, including antique surfboards, photographs and videos that chronicle the history of the surfing.

Locals will tell you that a visit to Haleiwa wouldn’t be complete without a stop at Matsumoto Shave Ice, where lines of sun-soaked people wait patiently to treat themselves to a rainbow-colored snow cone with a scoop of ice cream and azuki beans. It’s good stuff!

Each summer, the town puts on the Haleiwa Arts Festival, a lively event featuring art demonstrations, trolley tours, storytelling and live entertainment.

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