We climbed 1,300 feet up Kaupo Cliffs to complete a loop on along the edge of the Koʻolau Mountains above Waimanalo on the Koʻolaupoko Coast of Windward Oʻahu.
According to long time Hawaiian Trail and Mountain Club (HTMC) member John Hall, Kaupo Cliffs is an old club route — possibly an old Hawaiian Trail used by kūkini who were the messengers and couriers of the aliʻi aimoku (king of the island). The route is not immediately obvious — contouring back and forth between adjacent ridges to avoid steep rock faces — and has been “lost” and “refound” multiple times over the 100 year history of the club.
After multiple false starts over 3 separate attempts, Justin Ohara and I refound the route in 2010 in honor of the club centennial. Since the Kaupo Cliffs – TomTom Loop can be easily completely in half-a-day, we reasoned that the perfect time to do the circuit would be on the morning prior to the HTMC annual meeting. Our goal on the day of the meeting was to pass the route on to the next generation of hikers.
Included in our group were HTMC members Justin Ohara, Larry Lee, Clayton Kong, Karen Liliker, Jeanne Furukawa, Jennie Chadbourne, Udom Stamegna, Thea Ferentinos and I — who intended to descend the TomTom Trail to attend the HTMC annual meeting. Also in the group were Bushwhackers Pete Clines, Laredo Muredo, August Smith and Duc Ong – who are all also HTMC members but who were not attending the annual meeting. Instead, the Bushwhackers would lead the rest of group on a much longer loop to descend Hahaiʻone Windward — an obscure steep windward ridge that drops back down into Waimanalo scouted by Pete Clines. The rest of the group included the 808 Goonies (Joshua Serrano, Chenay Borja, Marcus Griego, and David Concepcion), CHASM (Crazy Hikers Ascending Steep Mountains) member Gene Witte, Oahu Hiking Adventurer Randy Glidden, and Baron Yamamoto who hikes with the Lost Trailblazers.
After slowly gaining elevation through tall grasses, groves of iron wood trees, and tangles of milo trees, we came to a dry stream-bed and climbed up a dry waterfall. It was a hot and humid day in the heavy brush and we were all sweaty by the time we reached the foot of ridge 4 where we took a short break.
After a short jaunt up ridge 4, we finally climbed above the vegetation and got our first views for the day. We could see the Koʻolau Mountains overlooking Waimanalo, the broad arc of the coast to Mokapu Peninsula, and the magnificent waters of the deep blue ocean.
The key to Kaupo Cliffs is a ledge within the fold between ridges 3 and 4 which allows hikers to contour easily over to ridge 3. We made our way through banyan trees along the conveniently situated ledge and contoured around the corner.
One of the beautiful sights we saw were mountain ʻilima flowers with red accents in the center. ʻIlima (Sida fallax) are indigenous to Hawaii and thrive along the coasts prostate to the ground. In the mountains, they assume an upright posture up to 8 feet tall.
When we reached the gully between ridges 2 and 3, the group split into two, one group continued on to ridge 2 to do the traditional Kaupo Cliffs route passed down through the club, while others headed up ridge 3 for a more challenging climb which Pete Clines had done several years before.
From ridge 2 we looked over to ridge 3 to see Pete Clines lead Chenay Borja, Marcus Griego, Gene Witte, and David Concepcion climb up the much steeper ridge which looked incredibly dangerous from our perspective. The rock was loose and the group dislodged a number of rocks — some a foot in diameter — which came crashing down. Fortunately, no one fell or was hit by the falling rocks.
The traditional Kaupo Cliffs route which climbs ridge 2 for most of the way is less steep and dangerous. However, the route is prone to loose footholds and falling rocks. Dangers exist throughout and the climb is not for the faint of heart.
The route up ridge 2 mostly follows the ridge line, but there are a couple of rock faces that can be avoided by contouring either to the left or to the right and then regaining the ridge line further up.
One of the more unusual endemic plants we saw along the way was maʻoliʻoli — the native carnation (Schiedea globosa) — which has tiny white flowers that were just coming into bloom.
After climbing up most of the way up ridge 2, the incline increased considerably and we reached an all crucial contour. The contour back to ridge 3 is situated over a steep drop-off and any slip at this point is likely result in a several hundred foot fall.
With a final scramble up the ridge, we were thrilled to top out and see Hawaii Kai on the other side! Since some of the HTMC members needed to prepare for the meeting, they did not linger at the top, and pushed-off immediately towards TomTom. But the rest of us waited for those coming up ridge 3 and relaxed — all the while soaking in panoramic views and enjoying each others company.
From the top of Kaupo Cliffs at about 1,300 feet elevation, we could see the broad sandy curve of Waimanalo Beach and the offshore islands of Manana (Rabbit Island) and Kaohikaipu (Turtle Island) towards Makapuʻu.
We were pleased when the group that scaled ridge 3 all made it up safely and learned a remarkable story. Thea Ferentinos started out late and was unable to follow our path — which underscores just how unobvious the route is. Thea ended up climbing up ridge 4 — an even gnarlier ridge!
Thea improvised her way up ridge 4 — getting tips from Pete Clines who watched from neighboring ridge 3 — and she made her way up ridge 4 without incident! Unfortunately, I could not see her from ridge 2 and no one seems to have gotten any photos of her making her way to the top.
After everyone made it to the top — whether from ridge 2, 3 or 4 — the group made its way westwards along the spine of the Koʻolau summit ridge.
We enjoyed spectacular views of East Oʻahu from the Koʻolau mountains as we climbed up and down several small puʻus (hills) along the way.
When we reached TomTom Ridge, the group that was continuing on to descend Hahaiʻone Windward posed for this group shot. Standing from left to right are Chenay Borja, Gene Witte, Marcus Griego, David Concepcion, Randy Glidden, Laredo Muredo, Pete Clines and Joshua Serrano. Duc Ong and August Smith are crouched on the ground in front of the group.
Just before the group pushed-off for their much longer loop and Hahaiʻone descent, Chenay demonstrated her balancing prowess by doing a “karate kid” pose on the top a telephone pole. For an account about the Kaupo-Hahai’one Loop check out the 808 Goonies.
After bidding farewell to the group, Baron Yamamoto, Jeanne Furukawa, and I descended TomTom Ridge to loop back to the HTMC clubhouse. TomTom is an old Hawaiian Trail rediscovered by HTMC club members Tom McGuire and Tom Cadle back in 1922 after the trail had fallen into disuse for almost 75 years in the decades following Western contact and was nearly forgotten.
The great thing about TomTom is that even though the trail loses considerable elevation over a short distance, there are ledges and foothold along the entire length of the trail, making the route relatively safe.
Out of the all of steep windward ridges found by HTMC that can be climbed up and over the Koʻolau Mountains to the other side of the island, TomTom is the only route deemed safe enough to be placed on the HTMC hike schedule.
While descending the TomTom Trail to make my way to the HTMC annual meeting, I could not help but reflect on the great time we had climbing up Kaupo Cliffs, admiring the magnificent views, and enjoying the great company. What a great hike!
WARNING: The Kaupo Cliffs and Hahaiʻone Windward routes are not for the acrophobic or faint of heart. The routes are extremely steep — approaching vertical in spots — and traverse crumbly rocks that are easily dislodged. The margin for error is small and any slip at an inopportune spot is likely to result in serious injury if not death. The routes should should only be attempted by trained climbers and mountaineers willing to undertake the risk of serious injury and/or death. It would be a good idea to have an advance medical directive and last will and testament in place before attempting any of these routes.
Native Hawaiian Plants, Department of Botany, University of Hawaii
Kaupo Cliffs – KauFaux Cliffs, Nate Yuen, HawaiianForest.Com
Refinding Kaupo Cliffs, Nate Yuen, HawaiianForest.Com
Kaupo Cliffs to Kuliouou, Dayle Turner, Post to Oahu Hiking Enthusiasts List, September 27, 1998