I’ve been driving O‘ahu’s Pali Highway since I first earned my license at age 15, my body now capable of traversing its eight or so miles of hills and turns almost by memory. The commute from my home near Kailua Beach to Honolulu—or town, as most locals call it—takes only about half an hour, so it’s more of a mental mountain than a long journey. But each time I drive to an appointment or to the private high school where I’m a substitute teacher, I am struck by something that makes me pause. It might be a lone cloud punctuating a lofty peak, a crevice conjuring memories of my youth, or wahi pana, a storied place of myth and history. The drive to town connects not only my small community to the city, but past to present.
After leaving Kailua, I’m often stopped at the Castle Junction traffic signal, just before the Pali climb begins. With my windows rolled down, I’m able to observe the natural world outside the field of cars. The trade winds float by, mynah birds scavenge the median grass, and leaves of kukui trees shield delicate shell ginger blossoms from the sun. And of course the sheer folds of the Ko‘olau Mountains are stretched above.
Although no signs reveal the name, this four-way stop is called Castle Junction because the estate nestled among nearby trees belongs to ancestors of missionary and businessman Samuel N. Castle, founder of Castle & Cooke Corp. The small plantation-style home to my left is now dedicated to managing Castle Foundation real estate, but to me it will always be the place where, as a teenager, my friends and I entertained ourselves on weekend nights. Sequestered in the old building’s parking lot, we met classmates and talked to boys we liked until the police sent us home. In the quiet of the day, this feels like a secret no one else in the cars around me knows.
The traffic light changes and I move on, navigating the curves of the Pali. I know exactly when to ease my foot off the gas, when to brake and when to accelerate through a turn. As the traffic slows at the hairpin turn, I notice hikers at the lookout ready to trek a lush forest trail deep into Waimānalo. It’s a hike I always mean to do but haven’t yet, although I have ascended Mount Olomana, rising 1,600 feet sharply into the sky just beyond.
Up the cars climb, and, just as I become impatient with slow drivers, I glimpse the runaway truck ramp on the opposite side, which never fails to make me smile. I acquired dubious fame among a new circle of friends for driving up the ramp one night in high school after a swim meet, just for fun. As intended, we were quickly stopped in the deep sea of rocks, but our laughter lasted as long as the pebbles rattled in the hubcaps.
The road curves on, and above looms the highest peak of the Pali, as well as portions of the Old Pali Road, built in 1932 over what was before simply a dirt path—the old above, the new below. A windblown lookout is perched on one end, 1,200 feet above sea level, offering unhindered views of an expansive valley extending to shimmering Kāne‘ohe and Kailua bays—green sea blending into vibrant turquoise. It’s also situated at the site where, in 1795, Kamehameha I fought O‘ahu warriors for control of the island, the notches where borrowed Western cannons once rested are still prominent.
After the bloody battle—thousands of bones were discovered during road construction—Kamehameha added O‘ahu to his list of conquered islands, and when the king of Kaua‘i agreed to a treaty, the island chain was for the first time unified. I can’t help but picture ancient warriors falling to their deaths below, the myth of their ghostly night march to the sea haunting my imagination every time I pass here. It truly is a path of fierce change, modernization and continuation.
Now entering the tunnels, yellow light aglow, the radio loses its signal and I wait to emerge in the otherworldly morning mist of Nu‘uanu rain forest. Distant waterfalls develop in the furrows of the Ko‘olaus; even if the weather has been dry, one ceaselessly plunges to the ground. Every time I pass by, I look for the small opening off the highway where we’d climb the fence and hike to that waterfall; hidden behind is a long passage to a two-chambered cave. Sitting inside, it feels as if you’re hiding inside the very belly of the island.
From the mountains descend a flood of trees—mango, guava, monkeypod and more—thick with climbing vines. Further ahead, ironwoods stand tall and in a grove, evidence of replanting reportedly led by King Kalākaua himself in the 1880s to recharge the aquifer depleted by cattle and deforestation.
At Waokanaka junction, the road flattens and Nu‘uanu’s grand past becomes visible. Hānaiakamalama, Queen Emma’s once secluded New England-style summer palace, rests alongside the highway and next to a shady park perfect for many afternoons spent looking at the clouds. After a brief peek at the ocean and Honolulu skyline, the road offers a swift tour of numerous churches and temples, as well as some of O‘ahu’s oldest estates, several now foreign consulates.
The highway is now at an end, so I turn onto a back road that skirts the base of nearby Punchbowl Crater. Others join the freeway queue, while some head straight into downtown’s business district, nestled near historic Chinatown, now a vibrant urban arts center.
Many who live in Honolulu boast about rarely undertaking this journey, while Kailua residents both cherish and accept it—it’s what we do. What is gained by living in my small beach community—and I’d argue from the drive itself—is much more valuable. It’s one that winds through personal and political history, extraordinary heights and striking beauty, to the city and home again. It is both where I come from and where I am going.