Kaupo Cliffs to Hahaione Windward: Oahu Ridge Trek

Published on April 9, 2011 by David G. Concepcion

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A month and a half hiatus from hiking can really take its toll, especially when one hikes among some of the best climbers on the island. That's exactly what I did on this day, and boy let me tell you, these guys can haul ass.

The History Behind the Route

In ancient times in Hawaii, messengers of kings would relay messages between two villages situated in Waimanalo and the area that makes up Hawaii Kai. The Tom-Tom Trail, a trail discovered in 1922, was likely an ancient Hawaiian trail popular among these messengers. However, during times of conflict, Kaupo Cliffs was regarded as a secret route and used as an alternative. When looking up at Kaupo Cliffs behind Waimanalo from a distance, they look menacing and nearly impossible to climb.

Starting the Ascent via Ridge #3

I got the chance to relive ancient history with Pete Clines, August Smith, Laredo Murray, Nate Yuen, Duc Ong, Gene Witte, and others from the Hawaiian Trail and Mountain Club. Also joining me was Baron Yamamoto from the Lost Trail Blazers, the 808 Goonies, and Randy Glidden! The planned route was to ascend Kaupo Cliffs, head ewa (west) towards the terminus of Tom-Tom Trail, and then proceed toward Mariner's Ridge or descend Tom-Tom, depending on group preference.

For this trip, I tested a GoPro monopod setup mounted to a Camelbak rig. We pushed off around 8:00 AM through a mile-long forest filled with tall grasses, haole koa, and tangled milo trees. Upon reaching the base of the cliffs, we contoured around several ridges. Kaupo Cliffs features seven distinct ridges: Ridge #2 is the easiest, while Ridge #7 is the notorious KauFaux Cliffs.

We initially began ascending Ridge #2, but after seeing Pete, Chenay, Marcus, Gene, and Laredo make their way up Ridge #3, I backtracked to attempt the "Pete route." The climb was steep and demanding, featuring imposing rock faces and a few dislodged boulders crashing down the slope.

Traversing the Ko'olau Summit Trail (KST)

After pushing through an ironwood grove and native koa trees, we reached the Ko'olau summit ridge to rejoin the group for a rest break. Pressing westward, we hiked toward the prominent white pole on Tom-Tom Trail, passing the terminal point of Kamiloiki Ridge in just five minutes.

With over 20 hikers lined up single-file along the open ridgeline, we enjoyed expansive views before reaching the Tom-Tom junction. Part of the group opted to descend Tom-Tom, while the rest of us continued along the KST toward Mariner's Ridge.

Descending Hahaione Windward

Upon reaching Mariner's Ridge, we decided to tackle an uncompleted windward descent: Hahaione Windward. The initial descent was steep, overgrown, and extremely narrow along a crumbling dike with loose rock underfoot.

About three-quarters of the way down, the ridge ended abruptly with a sheer drop above the tree line. Pete and August deployed ropes, allowing everyone to negotiate the 60-foot cliff face safely using available hand- and footholds. Once past the cliff base, we contoured right to exit the ridge safely, concluding an incredible 8-hour traverse along Oahu's Ko'olau Range.

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Labels: Kaupo Cliffs, Hahaione Windward, Kamiloiki Ridge, Koolau Mountain Range, Koolau Summit Trail, Mariner's Ridge, Oahu Hiking