Considering the rich history to be discovered along highway Route 99 (also known as Kamehameha Highway), from Wahiawa in Central Wahiawa and Waialua on Oahu’s North Shore, it comes as no surprise that a company named Route 99 (reminiscent of Route 66 in the heartland of the mainland) specializing in Hawaiian lifestyle caps and headwear, has become so successful.

The company began at the Haleiwa Farmers Market before opening its flagship store along Route 99 in Wahiawa. Route 99 celebrates the uniqueness of the North Shore, and its designs are created by local artists. Its products can be found at over a dozen locations on the North Shore alone, and at dozens of others on Oahu the Big Island, Maui, and Kauai.

Route 99 seeks to draw more residents and visitors to an area that often goes otherwise unnoticed. The company has created a map of points of interest along the highway, available for free at the company’s website

Route 99, the highway that is, boasts a number of notable sites, from sacred ancient Hawaiian grounds to iconic pop culture locations. Many if not most visitors and residents opt for the more direct route along Kamehameha Highway into Haleiwa town, but for intrepid travelers, Route 99 offers attractions that go largely unexplored.

Route 99 runs along Lake Wilson, the second largest reservoir in all of Hawaii. On the lake is Kemoo Farm, and Kemoo Pub, a funky pub and eatery catering to military personnel and families and a handful of community-minded motorcycle clubs. Don’t let that image spook you. It’s a fine spot for lunch on the way to the North Shore, or a snack on the way back. The pub was also featured in the famous movie From Here to Eternity, which starred Frank Sinatra among many other great Hollywood icons of a bygone era. Across the highway is Schofield Barracks, one of the most vital US military installations in the world.

Lake Wilson on Route 99 provides a perfect sanctuary for relaxation

Possibly the most important Hawaiian cultural site along Route 99 is a large grouping of birthing stones on the left, just past the junction to Kamehameha Highway. The mothers of Oahu’s Hawaiian royalty would travel from all over the island to give birth at the site, which is essentially the center, or belly button, of the island. Stories of strange, otherworldly things occurring at the site abound, and many native Hawaiians to continue to honor it as sacred. It was also the location of many ancient battles for control of parts of Oahu .

The highway Route 99 winds through a long tunnel of whispering ironwood pines into Waialua, a historic sugar cane producing region. It’s only a short, 10-minute drive into Haleiwa Town, where most of the North Shore’s commercial and retail activity are located.

A trip to the North Shore is always worth the drive. But taking the “long way” into Waialua along Route 99 before heading into its more famous neighbor Haleiwa is a great way to engage with old Hawaii on the journey. And Route 99’s unique, embroidered lids are a perfect way to remember a Hawaii vacation for years to come when you get back home.


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