Puu Kukui - a bucket-list ride
It took a little faith just to get there.
Northwest Maui (Pu‘u Kukui) Loop — September 2021
It took a little faith just to get there. September 2021 was still deep in the uncertainty of COVID—tests, forms, approvals, and more than a few crossed fingers—but somehow everything lined up. My sister’s gift of a week at her family’s timeshare in Kaanapali turned into a green light, and with my friends Rick and Jackie along for the trip, Maui welcomed us in.
I had one goal in mind: ride.
From Boss Frog’s in Lahaina I picked up a beautiful Cannondale Synapse—smooth, responsive, and ready for something big. And the ride I had in mind was exactly that: the Pu‘u Kukui loop, a true bucket-list route wrapping around the northwest shoulder of the island.
The day dawned just about perfect—sunny, warm but not oppressive, with that soft island breeze that hints at both comfort and challenge. Not long into the ride, I met “Kehie Bob,” a local character with a long gray beard and the easy confidence of someone who knows every bend in the road. He’d moved from the Bay Area years earlier and made this loop a weekly ritual. At 75, I was glad for the company—and even more for the guidance.
Bob became my rolling tour guide. He’d call out the climbs before they hit, point out overlooks I would have ridden right past, and eventually led me to a tucked-away shaved ice stand on the east side of the volcano that I never would have found on my own. The owner, a woman running her little oasis in near isolation, served up what might have been the best reward of the day.
The road itself demanded respect. Much of it was narrow—at times barely wide enough for a single car—with stretches where you wondered how traffic worked at all. And the terrain? Relentless. The route was either climbing or descending, with very little in between.
One standout was the Honokohau Bay Wall—a short but punishing section: about 0.6 miles with 247 feet of gain, averaging 11% and pitching up to 17.5%. It hit hard, but by then Bob had already warned me, and I dug in, turning over the pedals and enjoying the challenge.
We rolled through stunning scenery all day—coastal cliffs dropping into deep blue water, a quiet cove dotted with snorkel boats, and lush valleys opening inland. For the first 40 miles, Bob and I shared the work, trading pulls and stopping occasionally to take it all in. It felt strong, steady—one of those rides where everything just clicks.
About two-thirds of the way around, we came out of the mountains. Bob peeled off toward Kihei, and suddenly it was just me and the final stretch: roughly 20 miles back to Kaanapali.
That’s when the wind showed up.
As I turned north, it hit me square in the face—a steady, stubborn headwind that turned the last leg into a grind. There was no question of finishing—I didn’t have much choice—but it took everything I had left. Pedal stroke by pedal stroke, I worked my way back, knowing I’d earned every mile.
I slept well that night.
Looking back now, the ride stands out not just for the effort, but for the place and the moment in time. Lahaina, where I picked up that bike and began the journey, has since been devastated by wildfire. It’s hard to reconcile those memories with that loss. I’m grateful I experienced it when I did, and I’m not sure I’ll ever return—but that day, that loop, and the people I met along the way will stay with me.