I have been traveling for over 5 years now and have been fortunate enough to complete some of America’s best hikes. From the East Coast to the West Coast, I’ve conquered epic alpine lake hikes in Colorado, majestic Rainier hikes in Washington, and countless others that have only ignited my passion for hiking even more. I’ve now been lucky enough to add to that countless list with some of the best Hawai’i hikes on Oahu. These six Hawai’i hikes now live rent free in my mind and bring me a new level of excitement every time I step on the trail.
HAWAI’I HIKES
Before getting into my favorite Hawai’i hikes there’s some things you should know.
- PARKING
- Parking can be very difficult! Sometimes it would be worth it to Uber because most of these trails start just off a neighborhood, which are already lined with cars. You can be circling for a while trying to find an open spot or may have to walk further than expected.
- SMASH AND GRABS
- Unfortunately, smash and grabs are pretty common on Oahu. It is very important to make sure that you leave nothing valuable in your vehicle. Some will tell you to leave your car unlocked to avoid a broken window. That choice is yours. We may or may not have done that and allowed someone to steal a cooler, work scale, and home health equipment like gloves and masks, etc…
- DANGEROUS RAINFALL
- When it rains it pours on the island. For these difficult Hawai’i hikes, I would HIGHLY RECOMMEND avoiding going after a heavy rainfall or if you are expecting rain later on. The mountains on Oahu are very steep and because most of the rain stays in the mountains, the trails can be extremely slippery and muddy. The difficult trails are narrow with steep drop offs. With many deaths and frequent airlift rescues reported on these trails, it is better to be safe than sorry. Therefore, just avoid these hikes under rainy circumstances.
- HIKING WITH ALOHA
- Now using this phrase on every hike! Be sure to hike with Aloha. Meaning, be respectful, be courteous, be self-aware. Make sure to leave no trace and no trash. Listen to nature instead of music. All land should be respected but go the other extra mile on these Hawai’i hikes and hike with Aloha.
Now let’s get into it!
KAHEKILI TRAIL
Out of all of these difficult Hawai’i hikes, I would say Kahekili is the most difficult. There are many aspects that can make a trail difficult, whether that is a steep incline, lots of scrambling/climbing, overgrown or muddy terrain, long distances, and/or level of fear due to exposure. Kahekili Trail has it all. This trail was both mentally and physically challenging and it was less than 4 miles long. An out and back trail with an elevation gain of 1,791 ft, Kahekili was no joke.
PARKING & CAUTION
To access the trailhead, you will park just down the road from the Ka’a’awa fire department at the Swanzy Beach Park. You will then walk ~0.3 miles to the start of the trailhead by turning left just past the fire department and continuing on Huamalani St. The trailhead begins between the two houses at the end of the cul-de-sac. Please be courteous as you’re walking directly through a residential area.
There is a sign at the beginning of the trailhead warning you just how dangerous this hike is and how everyday people are being rescued from the Crouching Lion Trail, the connecting trail. When we finished our hike, we saw three people get rescued via helicopter. Therefore, be cautious and be smart. If you are unsure of your ability to complete a hard and dangerous hike, sit this one out. It is important that you are sure footed, won’t become paralyzed due to a fear of heights, and have the strength and endurance to complete this hike. If you feel confident and I didn’t scare you off yet, then you should totally hike Kahekili Trail because it is AMAZING!
THE ASCENT
For the first half a mile you are hiking through the forest ascending towards the tree line. There are already quite a few rope sections, and you will most likely encounter mud even if it hasn’t rained recently. Once making it out of the tree line the real fun begins! The trail will become very narrow and have steep drop-offs on both sides, but the views are incredible! There are about 4 points where you can stop to take a break, catch your breath, and soak the views in without feeling like you’re going to fall of the mountain.
During this mile stretch, there are more rope sections, high step-ups, and lots of scrambling. I felt like the majority of this hike I was on my hands. Using the 3 points of contact method was a MUST during the steep climbs for safety. The hike is difficult but oh so worth it to see views of the Kualoa Ranch and valley, the mountainside, and an ocean that stretches for miles.
SAVE YOUR LEGS
Although the hike does continue on to eventually meet up with the Crouching Lion Trail, I would suggest turning around before descending back into the forest. If you were to complete the trail, the next half a mile to mile is pretty brutal. The trail is very muddy with little to no ropes, the brush is overgrown, and there’s very few “epic” views. The trail descends back down into the forest and there is a small waterfall to see. But, in my opinion, save yourself the time, struggle, and scratches by turning around after finishing the exposed ridge line.
KULI’OU’OU RIDGE
Many Hawai’i hikes can go from sea level to 3,000 ft quickly. But, if you’re looking for something a little friendlier but still packs a punch, Kuli’ou’ou Ridge is the perfect trail!
PARKING
Parking for the Kuli’ou’ou Ridge isn’t too bad. You will have to park in a neighborhood and maybe walk further than anticipated, but you should be able to parallel park somewhere along Kalaau or Kuli’ou’ou Road.
TRAIL SPECS
This trail can be done one of two ways. An out and back with a distance of 4.4 miles and 1,666 ft or a loop at 4.6 miles and 2,211 ft composed of hiking two different ridge lines. (All Trails elevation gain may be a little off.)
We chose to do the out and back because it had rained earlier in the week and the loop offers more of an exposed route which could be a little more dangerous in wet conditions. The trail is very well maintained and has a consistent gradual incline throughout the whole hike. Yes, it is still difficult and has some steep sections with a little bit of scrambling but overall, it is a great trail with great views at the top!
CHALLENGING BUT REWARDING
The reason this trail is difficult is purely because of the incline. There are no rope sections, exposed cliff walks, or an unmanageable distance. The trail itself is really nice and would be great for those looking for something more challenging than they may be used to, with a great reward at the end. With sweeping views over the entire southeast corner of the island, it’s a sight to see, especially early in the day! I highly recommend this difficult hike!
MOUNT KA’ALA
Not only is Mount Ka’ala a must do because of the hike itself, but also because it is the highest mountain on Oahu! What a cool accomplishment to be able to say you hiked the tallest mountain on the island! Mount Ka’ala is a 6.8 mile out and back with an elevation gain (according to All Trails) of 5,311 ft, which is definitely incorrect considering the peak is only at 4,025 ft. I think we clocked in an elevation gain of around 3,500 ft. But regardless, it is a difficult hike!
PARKING
Parking for this trail is a little difficult. It’s kind of a lose/lose. Some say Uber will not drive back the entirety of the road to drop you off at the trailhead, but also this is a popular destination for those smash and grabs. So please make sure to leave your car empty of all valuables. Even things you may not think are valuable, will be valuable to someone else. You have been warned!
CONQUERING THE TALLEST MOUNTAIN ON THE ISLAND
The first mile of the hike is pretty laid back. You’re walking on pavement the majority of the time until you reach the forest. From there you will finally start making your ascent. It does get steep pretty fast. For the next two miles you’ll be in the trees. The bugs are bad, so bring bug spray if you can. You may even see a wild pig or two!
Once you get past the tree line, the real fun begins! For the next mile you will have insane views of the valley, the ocean, and the North Shore. You also get to do some scrambling, which we always enjoy. I would recommend bringing gloves with you. There are quite a few rope sections. You may not need them much going up but coming down we found them to be very useful! This section is a lot of fun, but also probably the most dangerous. There are a few sections where you are on the edge of the cliff. There is a fence and/or ropes to hold on to if needed. But just be cautious of foot placement and you’ll be fine!
INTO THE RAINFOREST
The last mile of the ascent towards the top is what makes this hike really unique. You’ll enter the rainforest. Because this is the tallest mountain on the island, the majority of the time it is covered by clouds. There is a thriving rainforest at the top, Mount Ka’ala Natural Area Reserve. It is a gated section, so be sure to close the gate behind you to keep out any unwanted critters that could affect the habitat. You’ll follow a narrow boardwalk that leads you right to the top of the mountain. If you’re taller, like me and my wife, you may have to crouch most of the time because of the hanging branches, but nevertheless still awesome!
Unfortunately, the summit is anticlimactic. You’re surrounded by trees, so you don’t have the great views like you did at other sections of the trail, BUT you just summited the tallest mountain on Oahu Island and that’s pretty awesome!
MOUNT OLYMPUS (‘AWA’AWALOA)
Before moving to Hawai’i and doing any research on Hawai’i hikes, I had a buddy tell me I had to conquer Mount Olympus. He said that it was the best hike on the island but not for the faint of heart. So naturally, I had to check it out for myself. He wasn’t lying. Mount Olympus was challenging but very rewarding in more ways than one.
PARKING
Finding parking for Mount Olympus couldn’t be easier! The trailhead starts in Wa’ahila State Park. There is a really big parking lot, so as long as you get there decently early you shouldn’t have any trouble finding a parking spot! Wa’ahila State Park is absolutely stunning and reminded me a lot of Washington State. Even if you’re not completing Mount Olympus you should definitely visit this park for a picnic, short stroll, etc.
THE MUDDY CLIMB
Mount Olympus, or ‘Awa’awaloa, is a 6 mile out and back with an elevation gain of ~2,000 ft. Again, our specs were different than those listed on All Trails. Nonetheless, the beginning of the hike is fairly easy and great for those with kids. The trail starts just off the parking lot and for about half a mile you’re walking on a very wide path in the forest. You’ll eventually break off to the left where things will start to get steeper and rockier. I think this section is still doable with kids. It’ll just be a little slower going. After about an hour of hiking you will come to your first viewpoint. If you are hiking with children, this is where I would suggest you turn around. From this point on, the hike gets steeper, narrower, and much much muddier.
The rest of the hike is a steady climb towards the top. Although, it is insanely muddy! Luckily, the trail wasn’t super narrow that we feared slipping and falling. We ended up embracing the mud and had a really fun time climbing towards the top! You will eventually reach the Kolowalu junction and can choose to turn around here if you’d like or continue to summit Mount Olympus.
In order to summit the mountain, you will encounter a more exposed and narrower trail. There are also many rope sections which can be difficult due to the steep grade. You will get muddy, no doubt about it. So, for those of you who like to hike in white Nikes, this may not be the hike for you… or your shoes. After climbing and clawing your way to the top you are rewarded with 360-degree views of the surrounding mountains, the Manoa and Palolo Valley, and Diamond Head Crater.
A fantastic hike packed with adventure, scenic views, and a great challenge! Highly recommend!
MOUNT OLOMANA (THREE PEAKS)
All of these Hawai’i hikes are difficult for different reasons. Mount Olomana (“Divided Hill“), aka Three Peaks, is difficult for many reasons. The elevation gain, the upper body strength needed to do countless rope climbs, and the mental fortitude needed to psychologically overcome this hike.
Mount Olomana is another hike in which many people have succumbed to death or injury. It isn’t a joke. This hike is cruel and should only be completed by experienced hikers. Like all other difficult Hawai’i hikes, if it has just rained or is going to rain, PLEASE avoid this hike! The majority of the trail is exposed and at some sections you are completing a technical 4th-5th class scramble. However, if you’re capable and willing to complete this hike you won’t regret it!
PARKING
There is no parking at the start of this trailhead, and you will be required to walk about a half mile to find parking. Some suggest parking at Maunawili Valley Neighborhood Park, I however wouldn’t suggest that. There are multiple signs stating you will be towed if you are not using the parking lot for the park itself. We parked along Auloa Road and didn’t have a problem. However, there are not designated parking spaces, and your car must be COMPLETELY off the road/sidewalk. Again, there are multiple signs saying you will get a ticket if you violate those rules. In fact, we saw a cop issuing many tickets to the vehicles that were even slightly parked on the sidewalk. I’m pretty sure they camp out there knowing this is an issue. Therefore, maybe uber to the trailhead, or park at your own risk.
GETTING TO THE TRAILHEAD
After finding legal parking, or catching an Uber, you will have about a half mile hike to the start of the trailhead. You’ll walk along Auloa Road towards Kalaniana’ole Hwy. From there you will take a right onto Loop Road. You’ll follow this Road until you meet the start of the trailhead. This is also the entrance to the Royal Hawaiian Golf Club, so be mindful of the coming and going traffic and avoid walking in the middle of the road.
You have now reached the start of the trailhead and are met with an ominous sign letting you know that there have been many deaths on the trail and to hike at your own risk.
PEAK 1
Honestly, from the start of the trailhead to the first peak isn’t that difficult or scary. There is one section where you have to do a vertical rope climb, and then at the summit of the first peak you will be exposed to the elements and steep drop offs. But getting to this first peak is only difficult because of the elevation gain. The majority of the time you are in the trees trekking towards the summit.
This section of the trail was mild-moderately trafficked. There are some big step ups and a little bit of scrambling, but overall, not too bad. Once you reach the summit the view is incredible! And if you decide to turn around at this point, which most hikers do, you’ve still completed a great hike with a great reward of a view of the second and third peak and surrounding mountains. Turning around after the first peak would be a great hike in itself and one I would highly recommend!
PEAK 2
As I said, most hikers stop after reaching the first peak. If you are not comfortable with heights and/or narrow trails on a mountain ridge with steep drops offs, now would be the time to turn around. If this doesn’t bother you, then keep trekking towards the second peak.
I personally didn’t think the trek from the first to the second peak was physically challenging. The hardest part is being completely exposed to the elements, walking on a narrow ridge line, and finishing with the exposed rope climb to summit the second peak. So, mentally it is a little more challenging if you have to overcome that fear of heights. But if you’re up for the challenge and you’re a confident hiker then I think summiting the second peak is totally doable for you!
You are again met with 360 views, just like the first peak, but this time you get to look back on what you’ve already completed which was a cool experience!
PEAK 3
Here is where things go from a physical and mental level of moderate difficulty to an extreme level of difficultly. Summiting the third peak is where accidents happen. Where people have fallen to their death. Please do not take this lightly. If the weather conditions are not *perfect*, if you physically or mentally are not in the right space then please turn around. The last section of this hike takes immense concentration, foot/hand work, full body strength, and both physical and mental endurance. Now is the time to decide to continue on or turn back. We continued on…
It was a decision that we didn’t take lightly. We went into this hike not knowing if we would complete it in its entirety or not, we wanted to make a game time decision, see how we were feeling and take things one step at a time. We both felt great and were ready to tackle the third and final peak.
At this point, the traffic was non-existent. We didn’t know how many people were in front of us and we couldn’t see anyone behind us. This allowed us to take our time and ensure proper footing and hand holds. You will be met with many rope sections at this point, some of which you will you have to put your full body weight into. Just pray those ropes are tightly secured! Especially during the initial 70 ft rope repel to start your descent towards the third peak. Throughout the rest of the hike from peak two to peak three you are walking along the narrowest ridge line, holding onto rocks and ropes for dear life.
Fortunately, I was able to finish the hike in its entirety which was an incredible experience! Being able to look back at the other two peaks to the North, see the Ko’olau Mountain range to the West, and the vast blue Pacific Ocean to the East was an incredible view that made the hike worth it in so many ways!
KNOWING YOUR LIMITATIONS
My wife on the other hand didn’t finish. We ended up running into those who were now on their return from the summit, and a large group had snuck up behind us. With about 10 people on a ridge where only one person can fit comfortably, she was a little shaken up. She no longer felt comfortable and sure footed and decided it was best to stay put and allow me to finish. I think that was a great decision for her knowing what the weight of continuing on a hike when mentally shaken up can cost people.
If you ever don’t feel confident in your ability to continue on it is perfectly acceptable to turn around and try again another day. You should be proud of whatever you can accomplish and take solace in the BREATHTAKING views you’ve already witnessed!
HONORABLE MENTION: KAMAILE’UNU RIDGE
Kamaile’unu Ridge holds a special place in my heart. It was the very first hike my wife and I completed after moving to the Island. It was also the mountain that sat in my backyard. So, for 9 months every day I looked outside and thought to myself, “I climbed that, b****”, which is pretty cool.
PARKING
Getting to the trailhead was easy for us because we just had to walk half a block to get there. But for those who don’t live at the base of the mountain you will most likely want to Uber there. Like most Hawai’i hikes, parking and break-ins are a constant battle. If you’re lucky enough to find a place to park, great! But on the flipside of that you may get your window smashed…
FROM MAKAI TO MAUNA
Once arriving to the trailhead, you have to find the start of the trail. The majority of this hike is overgrown. Therefore, navigating on the “trail” is very subjective. Just start climbing. For a little over a mile, you will climb up 1,587 ft. This out and back is a scramble towards the top, with overgrown brush, jagged lava rocks, and steep step ups. I would highly recommend starting early because there is no shade, and the rocks can get very hot throughout the day. Once you make it to the top though, the view of the valley is just incredible! Our first real hike from Makai (sea) to Mauna (mountain) was breathtaking.
You can continue on this hike towards the taller peaks, which I would recommend doing! It flattens out for a little while before climbing straight up again but you will be rewarded with more awesome views of the valley and surrounding mountains.
SHORT, STEEP & SWEET
The reason I decided to include this hike under difficult hikes is because of the incline, navigating the trail, and the amount of scrambling needed to be done. Kamaile’unu Ridge is a really short hike that offers stunning view of Waianae Valley, but navigating this trail and the elevation gain make it a difficult climb. It’s short, steep and sweet!
These difficult Oahu, Hawai’i hikes are some of the best hikes you will do in the country! They are unbelievably challenging, both mentally and physically. Yet, they also feel like an adult jungle gym with the rope climbs and scrambling. These hikes are not for the weak and if you really want to push yourselves give these a go! Just please whatever you do, lead with caution, safety, and that Aloha spirit. Have fun out there, friends, and good luck! Aloha!
If you have any questions regarding these Hawai’i hikes or any other related questions, please feel free to contact me!