Each summer, the town puts on the Haleiwa Arts Festival, a lively event featuring art demonstrations, trolley tours, storytelling and live entertainment. While the Haleiwa was set in the middle of nowhere, Dillingham had a plan. Looking back, its difficult to envision Haleiwa as being a sparkling resort area. Each winter, the North Shore becomes the centre of the surfing universe, with up to twenty foot waves challenging the sports best and bravest.

Designated a Historic, Cultural and Scenic District in 1984, Haleiwa has maintained its simple charm and laid back environment. Stroll through the funky town of Suitcase Trolley Haleiwa and its colourful assortment of surf shops, boutiques, art galleries and eateries. Haleiwa offers a nice selection of art galleries, surf shops and eateries.For a taste of Oahu, a Hawaii Island at its rugged best, head to the North Shore, a twenty mile stretch of coastline from Kaena Point to Turtle Bay. The hotel is gone now, but this old plantation town continues to welcome visitors. Locals will tell you that a visit to Haleiwa wouldnt be complete without a stop at Matsumoto Shave Ice, where lines of sun soaked people wait patiently to treat themselves to a rainbow coloured snow cone with a scoop of ice cream and beans. More than a century ago, however, before Waikiki built its first hotel, visionary businessman Benjamin J Dillingham opened Hawaiis finest lodging on a small strip of land between the Pacific Ocean and the Anahulu River.

The graceful frigate bird, he said, best exemplified the ambience he wanted to create for the hotel. 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. Visit the Suitcase Trolley North Shore Surf & Cultural Museum, established in 1999, located at the North Shore Marketplace. Aging storefronts line its main street.. For years, visitors and residents alike rode the train to spend some leisure time at the beachside resort. This sleepy little town, nestled comfortably along Oahus North Shore, is a complete 180 degree turn from the hustle and bustle of Waikiki. Shortly after, the town adopted the name Haleiwa. The museum features a wide range of surfing memorabilia, including antique surfboards, photographs and videos that chronicle the history of the surfing.

A favourite stop here is Matsumotos Shave Ice, a venerable landmark that serves the icy treat in a glorious rainbow of flavours. He named the grand Victorian hotel Haleiwa.