Oahu’s Most Adventurous Hiking Trails

Oahu's Most Adventurous Hiking Trails
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Oahu’s Most Adventurous Hiking Trails

I may be biased, but I like to consider myself the queen of finding adventurous Oahu hiking trails. If there’s an epic, slightly dangerous hike on the island, you can trust that I’m going to find it and, most likely, hike it for sunrise. I think I can speak for Cole and I both when I say, standing at the peak of a mountain, watching the sun awaken everything around you, is a hard feeling to top. If there’s a comparable feeling out there, we haven’t found it — yet. 

Whether you’re visiting Oahu or you are lucky enough to call it home, you don’t want to miss out on any of these adventurous hiking trails. We’ve hiked some pretty amazing trails around the world but nothing compares to the get-down-and-dirty hiking style of Hawaii trails. 

K1 and K2 Peaks, Oahu's Most Adventurous Hiking Trails

These hikes are guaranteed to have you scaling up or jumping in waterfalls, crawling up (and down) trenches, top-toeing across ridges, and throwing your arms out in gratitude at the breathtaking 360 degree views. 

Please note, all the trails on this list are not recommended for anyone afraid of heights or new to hiking, and should not be completed on windy or rainy days.

(p.s. wear good hiking shoes!)

1. Ka’au Crater

Distance: 7.3 miles
Ka'au Crater, Oahu's Most Adventurous Hiking Trails

Perhaps the most adventurous hiking trail on Oahu, Ka’au Crater offers just about everything: jungle vibes, waterfall dips, ridge walks, and epic views. The trail begins low in the valley before bringing you to the foot of a series of waterfalls. 

Ka'au Crater, Oahu's Most Adventurous Hiking Trails
Ka'au Crater, Oahu's Most Adventurous Hiking Trails

If you’re like us, you’ll probably look around for a bit, perplexed, before realizing that they only way to continue is to go up – this is where the fun really starts! We’ve hiked several hikes around the island but have yet to come across another trail that requires you scale up alongside a waterfall via rope to continue on the trail. 

Ka'au Crater, Oahu's Most Adventurous Hiking Trails
Ka'au Crater, Oahu's Most Adventurous Hiking Trails

Just when you think you’re at the top, you’ll realize there’s still several more waterfalls to climb. Who doesn’t love a multi-waterfall hike?! Once you reach the top of the waterfall series, you’ll head right to begin circling the rim of the crater (you can avoid the ridge and shorten the hike by going left – and coming back down the same direction). 

Views are in no shortage here, as once you reach the middle of the crater you can see across the island to the Windward, or, east side. This trail is adventurous, long, – not for the faint of heart – and bound to have you returning time and time again. 

Ka'au Crater, Oahu's Most Adventurous Hiking Trails

2. Kuliouou West Loop Trail 

Distance: 5.5 miles
Kuliouou West Loop Trail, Oahu's Most Adventurous Hiking Trails

The Kuliouou West Loop Trail is the lesser known, longer, way to hike the Kuliouou Ridge. Confusing to find at first, as you’ll veer left, avoiding the start of the marked trail, to stay on a paved road. This road will lead you to a building, where you’ll veer right into the woods. 

The trail doesn’t look like much at first, as it leads you straight up the hillside on a tiny footpath from the get go. Once you reach the top of the ridge, you pretty much stay there for the remainder of the hike. In my opinion, this hike is the most epic of all ridge hikes on the island, offering views of the Koolau Range not seen from any other trail.

Kuliouou West Loop Trail, Oahu's Most Adventurous Hiking Trails
Kuliouou West Loop Trail, Oahu's Most Adventurous Hiking Trails
Kuliouou West Loop Trail, Oahu's Most Adventurous Hiking Trails

If climbing up ropes, balancing across ridges, and laughing out loud at views you can hardly believe are real is your thing – *guilty!* – then you will love this hike just as much as we do.

Kuliouou West Loop Trail, Oahu's Most Adventurous Hiking Trails

3. Haiku Stairs (Stairway to Heaven) 

Distance: 2.5
*Please note that this hike is currently closed and can result in
$1,000 fines.
Haiku Stairs, Oahu's Most Adventurous Hiking Trails

Easily the most famous hike on Oahu, Haiku Stairs is sure to be unlike any other hike you’ve ever done. The stairs, originally built during World War II to provide access to a naval radio station, make up the entire trail as they wind up and down the ridge of the Koolau Range. 

Haiku Stairs, Oahu's Most Adventurous Hiking Trails
Haiku Stairs, Oahu's Most Adventurous Hiking Trails

The views from this trail are every definition of the word breathtaking — especially if you opt to do it for sunrise! In my opinion, the stairs and rails create a nice sense of security as you shimmy up and down the ridge, allowing you to fully soak up the scenery. 

Haiku Stairs, Oahu's Most Adventurous Hiking Trails
Haiku Stairs, Oahu's Most Adventurous Hiking Trails

There are a few questionable sections of stairs that, at times, feel more like a ladder. However, rest assured that these sections don’t last long. 

Also, keep in mind that clouds often roll in and out of the valleys, frequently, so if you don’t initially have a view give it a few minutes and it just might clear up. 

Haiku Stairs, Oahu's Most Adventurous Hiking Trails

Not your typical muddy, rugged Hawaii hike, and not even close to being one of the island’s longest hikes, but the trail is utterly epic, nonetheless. 

4. Awaawaloa (Mt. Olympus) via Waahila Ridge

Distance: 5.2 miles 
Mt. Olympus, Oahu's Most Adventurous Hiking Trails

Awaawaloa, or Mt. Olympus, was our first long hiking trail we completed on the island (at the time it was in our backyard #goals) and it’s been a favorite ever since. Mt. Olympus, is one of the highest peaks on Oahu and can be spotted from several locations around the island.  

Mt. Olympus, Oahu's Most Adventurous Hiking Trails
Mt. Olympus, Oahu's Most Adventurous Hiking Trails

The hike starts out more mild than most on the list but ends in a gnarly (read: super fun!) rope section and eventually takes you up onto the ridge. To reach the summit you’ll need to continue past the “trail ends here” sign, where you’ll be rewarded with views of both the east and south shores.

Mt. Olympus, Oahu's Most Adventurous Hiking Trails

5. Olomana Trail (Three Peaks) 

Distance: 4.4 miles 
Olomana Trail, Oahu's Most Adventurous Hiking Trails

Olomana, more commonly known as Three Peaks, is one of the more common hiking trails on the list and has a reputation that proceeds it. As the nickname suggests, the trail consists of three peaks you can summit, with the end goal being to reach the third peak – a feat many hikers choose not to endure. 

Olomana Trail, Oahu's Most Adventurous Hiking Trails
Olomana Trail, Oahu's Most Adventurous Hiking Trails

The first two peaks are relatively easy to access, while the third requires placing a lot of trust into a rope as you lower yourself down the mountain side, before beginning the climb back up, again. Being on the east side of the island, this is a perfect hike to do for sunrise and may even warrant you the trail all to yourself!

Olomana Trail, Oahu's Most Adventurous Hiking Trails

6. Mt. Ka’ala

Distance: 7.1 miles 
Mt. Kaala, Oahu's Most Adventurous Hiking Trails

Mt. Kaala is a must for any hiking fanatic as it is the official highest peak on Oahu at 4,026 feet. This hiking trail is the only one on the list that leaves from the west side of this island, warranting different views since you’ll be hiking in the Waianae Mountain Range, instead of the Ko’olau. 

Mt. Kaala, Oahu's Most Adventurous Hiking Trails
Mt. Kaala, Oahu's Most Adventurous Hiking Trails

Mt. Ka’ala is one of the hiking trails you love to hate, as every single step you take from the get-go is up until you reach the summit. This is not a trail to rush through as the beauty is in the process of reaching the top, rather than the top itself. 

Mt. Kaala, Oahu's Most Adventurous Hiking Trails
Mt. Kaala, Oahu's Most Adventurous Hiking Trails
Mt. Kaala, Oahu's Most Adventurous Hiking Trails

You’ll pass through dense forests, across ridges, and up rock faces, before walking across a set of wooded planks through the Kaala Nature Area Reserve (NAR) that protects 12 native and two rare communities of flora and fauna. After passing through the enchanted NAR the trail abruptly (and comically) ends at a “This is the end of the trail” sign in what first appears to be a less than average field. Don’t worry though, if you wander around at the top a bit you’ll stumble upon some worthy lookout spots. 

Mt. Kaala, Oahu's Most Adventurous Hiking Trails

7. Konahuanui Peaks (K1 & K2) via Kalawahine to Pauoa Flats

Distance: 9 miles
K1 and K2 Peaks, Oahu's Most Adventurous Hiking Trails

The trail leading to Konahuanui Peaks (K1 and K2 for short) is perhaps my favorite trail on the entire island – have I already said that? It’s so hard to choose! Most hiking trails on Oahu produce some pretty epic views, but it’s seldom that you come across a trail that rewards you with epic views at every turn. The trail to K1 and K2 is one of those trails, and the highest peak in the Koolau Mountain Range. 

K1 and K2 Peaks, Oahu's Most Adventurous Hiking Trails
K1 and K2 Peaks, Oahu's Most Adventurous Hiking Trails

These peaks have several routes that will lead you to them; personally, we accessed the peaks via the Kalawahine trail to Pauoa Flats. If you choose this track, the trail starts out mild and diverse through the forest and across planks before bringing you to your first lookout. From this lookout you go right and begin the upward and long climb to K2. From this moment on, the awe-inspiring, I-can’t-believe-I-get-to-live-on-this-planet views don’t stop. 

K1 and K2 Peaks, Oahu's Most Adventurous Hiking Trails

This trail will challenge you mentally and physically but will reward you with every step. After you reach the summit of K2 you’ll have the option to continue on to K1 via a .5 mile, overgrown ridge. K1 isn’t any more spectacular than K2 but you’ve already come so far, why not conquer both peaks?

* * *  

There you have it — a list of our favorite, adrenaline-pumping, push-you-out-of-your-comfort-zone, Oahu hiking trails.

Have you hiked any of them? Any other trails you would add to the list? 

Trust me when I tell you we really struggled to narrow this list down to a reasonable number… But, what can you do when you live in a place as magical as Oahu?

As always, keep adventuring x

KEEP BELIEVING. KEEP EXPLORING. AND, KEEP RELENTLESSLY TELLING THE UNIVERSE ALL IT IS YOU PLAN TO DO. 

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