10 Most Challenging Trails on Oʻahu
I was keen on avoiding the word 'hardest' when choosing a title for this post because these are not the hardest hikes on Oʻahu.
The hardest hikes on Oʻahu have names that most have never even heard of, which was not the intention of this post.
Rather, I wanted to create a list of the most challenging trails – trails with a clear starting point and ending point. This is why I left out both the Koʻolau (KST) and Waiʻanae Summit Trails (WST), as I wanted to keep this list to what one would more typically call a trail.
Furthermore, the following list excludes random hairline ridges, climbs/ scrambles, etc., because any long-time Oʻahu hiker would know this list could go on and on. While there are challenging ridge lines in the most unsuspecting places, perhaps that’ll be a future post.
All said, please take the following warning to heart, as it comes from a place of compassion, not cockiness. I have personally lost a close friend while hiking in Hawaiʻi, and I don’t wish the same for anyone.
Warning
Hawaiʻi hiking is harder than the mainland.
I have completed some of the more challenging hikes and climbs around the world, including Denali, Capitol Peak, and even Gannett Peak, all for the fun of it, and I can honestly say that hiking in Hawaiʻi is harder than anything I’ve faced elsewhere.
Casual days in areas that shouldn’t be sketchy can turn sketchy in just moments, and there have been many times on random day hikes in Hawaiʻi that have been far more sketchy and challenging than even the highest peak in North America could have thrown at me.
All said, most of the trails on this list aren’t that extreme in nature. That’s not to say that they don’t have their challenges, but by and large, the trails below are challenging and rewarding day hikes, not hairline ridges.
10 Most Challenging Trails on Oʻahu
With the exception of the first one, the following list is written in no particular order of best or worst.
I do think that it’s worth noting how the vast majority of trails on the list below come from the Koʻolau Mountain Range, which should show where the challenging hikes on Oʻahu lie.
1. Castle Trail
Distance: 9.3 miles / 15.0 km
The Castle Trail is the most challenging hike on this list because it’s easily the least-trafficked trail on this list.
If you know anything about Hawaiʻi hiking, trails that seldom get visited become overgrown quickly, which in the Castle Trail’s case, makes the descent into Punaluʻu Valley extremely challenging, even for the most experienced Oʻahu hikers.
Overall, the hike and the descent, particularly, will take some good route finding, which I encourage you to learn more about in my separate post.
Read My Separate Post: Castle Trail
2. Schofield-Waikāne Trail
Distance (Roundtrip): 14.0 miles / 22.5 km
As far as Nā Ala Hele State of Hawaiʻi trails go, the Schofield-Waikāne Trail is the longest and most remote on Oʻahu.
That being said, Schofield-Waikāne is nowhere near the hardest hike on this list, as it’s truly a gentle giant for what such a remote Oʻahu hike could be.
By this, I mean that the trail is as maintained as one could expect; much of the distance follows a road in the beginning, and the elevation gain from the true trailhead to the summit is only 700 ft. (213 m), making Schofield-Waikāne one of my favorite long Nā Ala Hele trails.
Read My Separate Post: Schofield-Waikāne Trail
3. Puʻu ʻŌhulehule Trail
Distance: 8.2 miles / 13.2 km
If you look at the sunrise photo above, Puʻu ʻŌhulehule is the pyramid looking peak on the right side of that photo.
However, compared to Schofield-Waikāne above, Puʻu ʻŌhulehule is absolutely the more challeging hike.
This is because the long, muddy, wet approach through Kahana Valley just to even start climbing Puʻu ʻŌhulehule is a mission of its own. Then, once you’re deep in Kahana Valley, the trail begins ascending steeply up Puʻu ʻŌhulehule, where all of the elevation gain is crammed into a short distance, and it’s not on the ridge you see leading up to the peak in the photo above. It’s behind, and it’s steeper!
All said, Puʻu ʻŌhulehule is a challenging but fun Oʻahu day hike, as long as you’re up for some very steep climbs and have good navigation skills to trek through the dense, wet Kahana Valley.
Read My Separate Post: Puʻu ʻŌhulehule Trail
4. Tripler Ridge Trail
Distance: 9.2 miles / 14.8 km
Next to other more popular trails in central Oʻahu, like the Stairway to Heaven, the Tripler Ridge Trail is one of the least-trafficked hikes in the area.
That being said, there isn’t too much to say about the Tripler Ridge Trail, except that the ridge is a long, minimally trafficked hike that ascends a remote peak in the southern Koʻolaus.
Know that if you have a valid DOD ID, you can hike Tripler Ridge beginning from the Tripler Army Medical Center, which essentially cuts out a lot of elevation gain that you would otherwise have to climb via Moanalua Valley if you did not.
Read My Separate Post: Tripler Ridge Trail
5. Kapālama Ridge Trail (Puʻu Lanihuli)
Distance: 7.6 miles / 12.2 km
Puʻu Lanihuli is that first peak with the golden light on it in the photo above.
On top of this, Puʻu Lanihuli is one of the most prominent peaks acting as the backdrop of downtown Honolulu. But even though it’s so close to the city center, Kapālama Ridge is often overshadowed by more popular nearby trails, such as Puʻu Kōnāhuanui, which is the further of the two peaks in the photo above.
Read My Separate Post: Kapālama Ridge Trail
6. Kūlepeamoa Ridge Trail
Distance (Roundtrip): 5.3 miles / 8.5 km
As far as southern Koʻolau ridges go, Kūlepeamoa is easily the most challeging.
This is because comparable neighboring hikes, like Wiliwilinui and Hawaiʻi Loa Ridge, begin high up in residential neighborhoods, while Kūlepeamoa begins on the Pia Valley floor.
Therefore, the elevation gain on Kūlepeamoa, along with the long ridge ascent to reach the summit, is one of the more challenging hikes in the southern Koʻolaus, but even so, it doesn’t even come close to others on this list.
Read My Separate Post: Kūlepeamoa Ridge Trail
7. Keaʻau Middle Ridge Trail
Distance: 5.4 miles / 8.7 km
The Keaʻau Middle Ridge Trail is a challenging west Oʻahu hike for a few reasons.
First, Keaʻau Middle is very steep, meaning all of the elevation gain is condensed into a short distance at the back of Keaʻau Valley that gains just under 3,000 ft. (914 m) from the trailhead to the summit.
Second, the Keaʻau Middle Ridge has numerous high-exposure sections where one cannot fall, or it would almost certainly mean death. While Keaʻau Middle is wider than many other Oʻahu ridges, I think that it makes for a great challenge to see if you’re ready for something harder than the hikes on this list, some of which I mention at the end of my Keaʻau Middle post.
Read My Separate Post: Keaʻau Middle Ridge Trail
8. Mānana Ridge Trail
Distance: 11.6 miles / 18.7 km
Compared to Schofield-Waikāne mentioned above, the Mānana Ridge Trail is easily the harder of the two.
The reason I even bring up Schofield-Waikāne is because it is the most comparable hike to Mānana, but where I call Schofield-Waikāne a gentle giant, Mānana is known as the rollercoaster on account of all its ups and downs over the course of the long ridge ascent.
All said, the views from the summit of Mānana are one of the most rewarding, which is why I encourage you to hike in good weather only for the amount of effort put in.
Read My Separate Post: Mānana Ridge Trail
9. ʻAiea Ridge Trail (Stairway to Hell)
Distance (Roundtrip): 11.6 miles / 18.7 km
Of all the trails on this list, the ʻAiea Ridge Trail only falls short in terms of difficulty to the Castle Trail, and it may be tied with Puʻu ʻŌhulehule.
That’s just one person’s opinion, but for as popular as the ʻAiea Loop Trail is, few hikers venture past the loop and onto the ridge, which traverses through some of the more rugged sections of Oʻahu’s Koʻolau Mountains.
That being said, if you think you’re up for the challenge, which requires carrying multiple days' worth of water for an overnight trip, the ʻAiea Ridge Trail to Stairway to Hell makes for one of the best overnight backpacking trips on Oʻahu.
Read My Separate Post: ʻAiea Ridge Trail (Stairway to Hell)
10. Lulumahu Ridge Trail
Distance (Roundtrip on Lulumahu Ridge): 4.6 miles / 7.4 km
Distance (Lulumahu Ridge to Nuʻuanu Trail): 9.0 miles / 14.5 km
The Lulumahu Ridge Trail is a deceivingly challenging hike, as the distance on the ridge is only 2.3 miles (3.7 km) each way.
However, this extremely short distance climbs to the summit of Puʻu Kōnāhuanui, the highest peak in the Koʻolaus, inherently making the hike one of the shortest and steepest on this list. Lulumahu Ridge has sections that are comparably as steep as the Puʻu ʻŌhulehule Trail mentioned above.
This is why two distances are listed above, as it’s more practical to hike Lulumahu Ridge one way, coming down and making a loop of it through Tantalus on the much more gradual Nuʻuanu Trail.
Read My Separate Post: Lulumahu Ridge Trail
Bonus: Kolekole Trail (Puʻu Hapapa)
Distance: 3.1 miles / 5.0 km
The Kolekole Trail to Puʻu Hapapa may be the easiest of the most challenging hikes on this list, but the Puʻu Hapapa Trail is only one of the more challenging hikes if you choose to hike up the WST side of the loop, which is the route shown in the post linked below.
Overall, Puʻu Hapapa is one of the more fun high-exposure trails on Oʻahu, but while I think it’s a fun scramble, the consequences of falling from the ridge are at their highest, as you can see from the cliffs below the peak in the photo below.
All said, the Kokekole Trail is only open on select weekends, and access to the trail can be tricky, which is why I encourage you to read through all the details in my separate post.
Read My Separate Post: Kolekole Trail
My Thoughts on Popular Challenging Oʻahu Trails
If you were to Google 'Hardest Hikes on Oʻahu,' you would almost certainly see answers such as the Koko Crater Stairs, Stairway to Heaven (Haʻikū Stairs), and the Mt. Olomana Trail (Three Peaks).
However, I can you that all of these answers couldn’t be further from the truth.
Therefore, I wanted to address these popular trails and why I believe their challenges don’t find their way on my list as the most challenging hikes on Oʻahu.
1. Mt. Olomana Trail (Three Peaks)
Distance (All Three Peaks): 2.9 miles / 4.7 km
If I didn’t mention Mt. Olomana, many hikers might be wondering why. To this I say, even with all the class 4 and 5 scrambling on Mt. Olomana, I don’t feel that this alone makes it as one of the most challenging trails on Oʻahu.
Furthermore, Mt. Olomana, also known as Three Peaks, is an extremely well-trafficked, short, and decently maintained trail. On every steep section of the trail, the ropes are replaced often enough, and the same can’t be said about other hikes on this list, like Puʻu ʻŌhulehule, which may use electrical cords for ropes on the steepest sections.
While Mt. Olomana easily has its own respective challenges, such a popular and well-kept trail simply doesn’t make it the most challenging.
Read My Separate Post: Mt. Olomana Trail (Three Peaks)
2. Stairway to Heaven (Haʻikū Stairs)
Some would say that Stairway to Heaven, via the long 10-mile (16.1 km) roundtrip Moanalua Middle Ridge, is one of the hardest hikes on this island, but in reality, it’s one of the easier hikes compared to the list above.
If I had chosen to include the Moanalua Middle Ridge on the list above, I would have said that it was the easiest option on the list for many of the same reasons as Mt. Olomana.
Therefore, since Stairway to Heaven is so popular, the back way up the Middle Ridge is one of the most trafficked trails on the island, meaning it doesn’t even come close to some of the others mentioned previously.
Read My Separate Post: Stairway to Heaven (Haʻikū Stairs)
3. Koko Crater Stairs
Distance (Roundtrip): 0.9 mile / 1.4 km
Elevation Gain: ~885 ft. / 270 m
In my opinion, the Koko Head Stairs are more challenging than the Haʻikū Stairs (Stairway to Heaven), but that’s only because the intensity of the trail is harder.
However, Koko Head is essentially a quick and popular evening workout for Oʻahu residents, making it a high-intensity but short adventure.
This is why trails listed above with more overgrowth, climbing, route finding, etc., all make it higher on this list in terms of difficulty than the popular Koko Crater Stairs.
Read My Separate Post: Koko Crater Stairs
4. Pali Notches Trail
Distance: 0.8 miles / 1.3 km
Some would say that high-exposure along the cliffs of the Pali Notches Trail make the hike one of the most challenging on Oʻahu, and I would only agree if the discussion was the Chimney and on to Puʻu Kōnāhuanui (K1).
However, the vast majority of hikers don’t venture past the first notch. What I would say is that the first is the easiest, the second is where it starts to get challenging, and the Chimney up to K1 is the hardest. That section in itself would make my list, but I wanted to exclude the Koʻolau Summit, as it’s not a trail in the traditional sense.
Overall, if you choose to hike up the Pali Notches, don’t do anything that you’re not comfortable with, as the difficulty on the trail increases dramatically beginning with the first notch.
Read My Separate Post: Pali Notches Trail
5. Mt. Kaʻala Trail (Tallest Peak on Oʻahu)
Distance: 7.1 miles / 11.4 km
Elevation Gain: ~3,400 ft. / 1,036 m
As any experienced hiker should know, tallest doesn’t necessarily mean hardest.
The same is true when it comes to Mt. Kaʻala. Which is why if you want to reach the tallest peak on Oʻahu, you’re in luck, as Mt. Kaʻala is a much easier day hike than any on the list above.
Overall, Mt. Kaʻala is also what I would call a gentle giant, much like the Schofield-Waikāne Trail. In my opinion, it makes for a fun uphill challenge, and I think most experience Oʻahu hikers would agree!
Read My Separate Post: Mt. Kaʻala Trail
Native Hawaiian Plants on Oʻahu Trails
I wanted to include this last section on this post because this is a subject that’s personal to me.
The native plant biodiversity in Hawaiʻi is insane! 90% of the native plants that you will see around the islands are found nowhere else on earth, and I say these things for two reasons.
The first is that I ask that you please do everything you possibly can to minimize your impact on our trails because so many of our native plants are at risk of extinction. The second is that if you have personal interest in the subject or may be curious about something that you found, I wrote a separate post entirely about native Hawaiian plants. I wrote it to help others around Hawaiʻi ID anything that you might be curious about.
For example, this species in the photo below can only be found on the island of Oʻahu and nowhere else on earth.
Read My Separate Post: Native Hawaiian Plant Guide
