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13 of the Most Insane Oahu Hikes

Soak in the stunning views of Oahu from one of its best hiking trails. These 13 Oahu hiking trails will get your adrenaline pumping while offering some of the best views of the island.

13 of the Most Insane Oahu Hikes

If you’re looking for some seriously surreal hikes with jaw-dropping views through lush jungles, then Oahu is beckoning. Part of the chain of islands that make up Hawaii, Oahu boasts some of the best hikes in Hawaii.

On any one of these Oahu hikes, you’ll get the chance to explore the island at your own pace, soaking in the wild nature and stunning scenery.

Even if you’re not an avid hiker, there are some easier and less-intimidating hiking trails. From the leisurely climb up the Manoa Falls Trail to the hair-raising sheer drops of the Seven Falls Trail, Oahu hiking trails have something for everyone—all surrounded by indigenous plants and wildlife.

So if you’re hungry for an adventure and eager to explore the hikes and incredible dense wilderness of Oahu, then let’s chat.

The best Oahu hikes are the kind of hikes that you’re going to remember forever, and we’re here to help you get started.

The Best Oahu Hikes, Hawaii

Best Hikes in OahuDifficultyLengthLocation
1. Diamond Head Hike Moderate1.5 milesKapahulu
2. Manoa Falls TrailEasy1.6 milesHonolulu
3. Seven Falls Hike OahuModerate-Hard2.1 milesHonolulu
4. Ehukai Pillbox HikeModerate2.1 milesHaleiwa
5. Crouching LionModerate.4 milesKoolauloa
6. Pali NotchesHard.7 milesKailua
7. Wiliwilinui Ridge TrailModerate4.5 milesHonolulu
8. Pink Pillbox HikeModerate1.2 milesNānākuli
9. Ka’au Crater HikeHard5 milesHonolulu
10. Koko Head TrailHard1.8 milesHonolulu
11. Three Peaks/Olomana Trail Hard 4.5 milesKailua
12. Tom Tom Trail Hard 6.6 milesHonolulu
13. Haiku Stairs (Stairway to Heaven)Hard 2.4 milesHonolulu

1. Diamond Head Hike

Since it’s close to Waikiki—the most famous of all Oahu beaches—it makes sense that Diamond Head is one of the most well-known Oahu hikes. It’s got stunning views and you don’t even need to work so hard to get there.

But fair warning: That means that it’s touristy, too.

Originally named by ancient Hawaiians as Le’ahi (which translates to “tuna ridge”), this old volcanic crater is a beauty and is actually pretty easy for all levels of hikers. It’s the kind of trek that looks like it’ll take you days with a guide and a donkey train to navigate, but the reality is thankfully far less daunting.

Diamond Head Oahu aerial shot
Diamond Head from above

The Diamond Head Trail hike time is only 40 to 70 minutes, which gets you up to around 760 feet above sea level. That’s where there’s a beautiful 360-degree vista; you can see the skyline of Waikiki, look down into the volcano’s caldera, and stare right into the blue oblivion of the never-ending horizon. No wonder it’s so popular and considered one of the best hiking trails in Oahu, right?

Difficulty: Moderate
Length: 1.5 miles
Location: Kapahulu

2. Manoa Falls Trail

If you’re more about a nice walk rather than a big, sweaty hike, Manoa Falls trail is where you’ll find some of the best hiking Oahu has to offer. It might be a little busier than other Oahu trails, due to its ease (it’s only a mile and a half!), but that doesn’t mean it isn’t worth your time.

The trailhead starts at the Paradise Park building at the top of Manoa Road, just a little way from the main city of Oahu—Honolulu—where you can catch a bus. It’s actually a very well-maintained route, and the path gently winds its way through the lush rainforest under the shade of the twisting trees.

Oahu aerial shot
Getting some aerial views before heading out on some Oahu hikes

You’ll have stunning views along the way, and the eventual sight of the gushing, 150-feet-tall Manoa Falls will reward you for your efforts. Who doesn’t like a waterfall?

Unfortunately, you’re not allowed to swim in the pool beneath the falls. It’s forbidden (and ill-advised, rule-breakers!) due to the water-borne bacteria that lurk in the stagnant lower pool. In other words: You can get really sick if you take a dip in there.

Difficulty: Easy
Length: 1.6
Location: Honolulu

3. Seven Falls Hike

This one is truly for the hardcore hikers out there, but is one of the best hikes in Honolulu. The Seven Falls hike on Oahu will get your heart pumping. Be ready for Oahu’s dense jungle and rocky terrain. Don’t expect to see any locals or other hikers out and about on your walk; few people know the trail. However, it’s the lack of other people that makes the experience even more incredible.

The main part of the trail runs along the bottom of the valley. No one sign-posted it very well, but, as long as you follow the valley, you should be fine. It might take a couple of hours until you reach the first waterfall. But, once you’re there, splashing in the water and cooling off will relieve you.

Continue further along the valley and you’ll find bigger and scarier falls to climb.

There are ropes that people have put in place so that it’s easier to scramble over the rocks. But, they’re wet, so I advise a lot of caution. And don’t forget that you’ll have to come back down the falls to get home!

This Oahu hike really is like a crazy Indiana Jones-style adventure, so just look after yourself. Wear sensible footwear and don’t do anything that you don’t think you can do. Know your limits.

Difficulty: Moderate-Hard
Length: 2.1 miles
Location: Honolulu

4. Ehukai Pillbox Hike

I love a trail with a weird name, and the Ehukai Pillbox Hike does get you wondering about where the hell you’re going (though a lot of the names on Oahu seem to follow these guidelines). This top hike is a little like a hidden gem, known mainly to the Oahu locals who often enjoy climbing up for sunset views.

Starting at the Sunset Elementary School (why didn’t my school have such a cool name?), the trail makes its way uphill pretty steeply over the roots of trees and big rocks.

The hike itself only takes around half an hour in total, but it’s an arduous climb. The trail gets so steep after a little while that ropes have been tied on the side of the hill to make it easier to climb up.

Hikes to Ehukai Pillbox at Sunset
Ehukai Pillbox—One of the lesser-known hikes in Oahu

Once you reach the top, there are two pillboxes here. The lower one has nice views of the North Shore Coastline. But, if you make it to the second pillbox higher up, you’ll be more than pleased with yourself for sure. And the views are even more spectacular, too.

Difficulty: Moderate
Length: 2.1 miles
Location: Haleiwa

5. Crouching Lion

Possibly one of the coolest-named Oahu hikes, Crouching Lion—near the community of Kaawa, Kaneohe—offers up some panoramic delights. But that’s only after a steep and fairly challenging climb up the “Crouching Lion” itself. I mean, it’s going to be a steep hike if you can reach views this astounding after only 30 to 45 minutes of trekking.

When I say trekking, it’s more like… yeah, climbing. Portions of this hike involve relying on ropes, but that’s only in the more slippery patches for balance. So your life is literally in the hands of a stranger’s rope-tying skills. Some of the ropes are a little sketchy, which might be the reason why Crouching Lion isn’t officially open.

Hiking Crouching Lion in Oahu
These views are worth it!

However, that doesn’t deter a lot of intrepid hikers, travelers, backpackers and outdoors lovers from making the strenuous scramble up to the top of Crouching Lion for its breathtaking views of the surrounding jagged scenery.

Tip: Hiking boots or trail runners with good traction would make this hike less difficult, for sure.

Difficulty: Moderate
Length: 0.4 miles
Location: Koolauloa

6. Pali Notches

The Pali Notches got a bit of a name for itself as being (more than) quite dangerous, so I wouldn’t try it out unless you’re a confident hiker.

This hike heads steeply upwards, where amazing views of the Pali Highway to your left and Kaneohe to your right will greet you. The path does actually get dangerous in parts; there are sheer drops and strong gusts of winds that can blow you off at certain points. No, really. Some spots also have an anchored rope to hold onto that will prove the difference between life and death.

Oahu's Pali Notches view
Pali Notches—One of the best hikes in Oahu but also one of the most demanding.

Pali Notches—One of the best Oahu hikes but also one of the most demanding.

There are also some parts of the trail that require you to climb up a vertical rock, but as long as you’ve got good shoes (traction and grip), and someone to hike with, you should survive.

Difficulty: Hard
Length: 7 miles
Location: Kailua

7. Wiliwilinui Ridge Trail

The Wiliwilinui Ridge Trail is a great four-and-a-half-mile out-and-back hike that heads right up to the top of a mountain… and then down again. It’s one of my favorite Honolulu hiking trails because, when you get towards the top, you end up walking through the cloud. That’s a pretty surreal experience.

All you have to do is head east out of Waikiki on the Kalanianaole Highway. Then turn left onto Laukahi Street and carry on towards the mountain. You have to check in with security at some point. Then you go left again on Okoa Street and the parking lot is at the end. There, you’ll find the trailhead and set off on one of the best hikes Oahu has to offer!

You’ll then find a lightly challenging combo of climbing stairs and low-key climbing rocks. Although there aren’t any cliffs involved, so mortal peril remains pretty low on this trail. It can get pretty muddy on this one, though, so be careful of slipping.

Difficulty: Moderate
Length: 4.5 miles
Location: Honolulu

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8. Pink Pillbox Hike

The Pink Pillbox Hike to a, uh, pink pillbox, is short. But it’s also a little risky. Located on the west side of Oahu, the start of the hike is along Kaukama Road, where you’ll find plenty of parking.

It’s actually quite a versatile hike in Oahu since it’s got two difficulty modes in the form of two different routes: One is a little easier but longer, while the other is much more challenging and also shorter.

Essentially a ridge hike along what’s known as Pu’u O Hulu, the easier trail winds around the ridge itself. On the other hand, the more difficult version of the Pink Pillbox is a hard climb up steps that have been formed in the rocks over many, many, many years.

Depending on whichever route you take, incredible views of the Maili coastline will greet you from the pink pillbox at the top of what’s considered to be one of the top hikes in Oahu.

Though exploring the pillboxes up here is fun, there’s a poignant reason behind the bright pink one; it’s a dedication to “the survivors, the fighters and to those who have lost their battle to cancer.” So here’s a chance to sit and ruminate on life, high above the powerful scenery below.

Difficulty: Moderate
Length: 1.2 miles
Location: Nānākuli

9. Ka’au Crater Hike

Fans of feeling like they’re trekking through a rainforest in survival mode will love the Ka’au Crater Hike in Oahu. Literally about five minutes after you embark on this hike, you’re in a world of tall trees, vines and muddy trails, which makes this feel like a real adventure in the wilderness.

It’s not only jungle trekking that you’ve gotta be able to handle though; there’s some rope climbing and rock scrambling to be done on this top Oahu hike, too. They make it quite the challenge. For this one, I’d recommend adventurous (and fit) hikers only. The uneven terrain and the length of the hike (five miles in about five hours) make it a pretty strenuous journey.

It’s not all challenging though; there are some amazing parts to this hike. For instance, you get to pass three gushing waterfalls, do some ridge hiking in Oahu, marvel at the rainforest… Just make sure your shoes are sturdy and have good grip. And don’t forget lunch. No one wants to get hangry on a tricky hike, do they? This one is certainly one of my favorite Honolulu hikes.

Difficulty: Hard
Length: 5 miles
Location: Honolulu

10. Koko Head Trail

If you feel like you need a good workout, the Koko Head Stairs is the hike for you. While walking up to the tops of hills, ridges, mountains and cliffs to get amazing views is a pretty cool thing to do in and of itself, doing it along a trail or path that’s got a bit of originality to it always makes the trip a little more fun. That’s what makes the trail up to Koko Head so unique: It’s along an abandoned railway!

Aerial shot of Koko Head, Oahu
One of the best hikes on Oahu is Koko Head

As with many of the hikes on Oahu, the Koko Head Trail runs through and up the side of a volcanic crater. The plus side is that the old railway track acts as stairs on the climb up to see the dramatic views this hike offers. The downside is that, well, they’re stairs. There are 1,048 railroad steps to the end of the railway, and then about another 30 feet of walking to get to the lookout points.

Though this is a short-ish hike, it still takes between 30 minutes and one hour to reach the summit. Then you’ve got time to relax, admire the view and drink some water (stay hydrated, people!) before you even contemplate the way down. Locals who are used to this walk actually run up this trail—even though it’s also locally known as the “Stairmaster from Hell.”

Difficulty: Hard
Length: 1.8 miles
Location: Honolulu

11. Three Peaks/Olomana Trail

Looking for a good, old-fashioned hard hike? Then you should try out the Three Peaks Trail, also known as the Olomana Trail. Of course, a trail called Three Peaks was never going to be an easy hike, and this one totally isn’t.

Starting near Kailua, the first of the three peaks is actually pretty simple. Surrounded by wildflowers, it’s also super scenic. There are some parts where you have to climb over rocks, but it’s nothing too difficult.

It’s when you have to ascend the second peak that things start getting a lot harder. There are some tree roots and ropes along the trail to help you out. And, as you make your way along the path, things start to get a lot more narrow and, well, terrifying.

The third and final peak might put you off the hike altogether. You’re going to need some good upper body strength to haul yourself up there. But just think of the satisfaction and the immense views across the treetops when you do. Fit, confident hikers only on this four-and-a-half–hour, four-and-a-half-mile hike.

Girls on a windy in Oahu
*Those post hike feels*

Difficulty: Hard
Length: 4.5 miles
Location: Kailua

12. Tom Tom Trail

The Tom Tom Trail might not be one of the most well-known hikes on Oahu. But it’s one of the most spectacular. And, without a doubt, one of the best hikes Honolulu has to offer. Beginning at the Makapu’u lookout, the path runs along a fence where you can come across for fairly amazing viewpoints.

The good thing about this hike is that, because there are so many pretty vantage points so early on in the trail, if you don’t feel like walking the whole way, you don’t need to.

But it is very steep from the start. It may make you wonder why you didn’t decide to have a day on the beach instead of doing a crazy hard hike. But the climb doesn’t last long. And panoramic views over Makapu’u Lighthouse, the beach and the deep blue ocean below will be a treat.

Difficulty: Hard
Length: 6.6 miles
Location: Honolulu

13. Haiku Stairs (Stairway to Heaven)

Like Diamond Head, the Haiku Stairs—aka the Stairway to Heaven—is a famous hike in Oahu. Or maybe the word should be infamous. There are two ways to the Insta-famous viewpoint at the top: one totally legal, and the other totally illegal.

You can try to ascend from the front, but there are security guards on duty 24/7 who will call the police if they catch you. Upon return, the cops will be waiting for you with a hefty fine of $1,000 USD.

If you’d rather not run the risk of a run-in with the police, there’s a back way.

View from Oahu's Stairway to Heaven hike
View from the top of the Stairway to Heaven, one of the most famous hikes in Oahu

The stairs themselves lead to a US Navy Radio Station antenna and were initially built as a backup means to access the antenna should other forms of access—like helicopter—not be possible.

Used officially until the 1950s, the 3,992 steps to the top were closed to the public in 1987. Now, “No Trespassing” signs are everywhere, though they’re often ignored.

US Navy Radio Station antenna at the top of the Stairway to Heaven hike
The radio antenna at the top of the famous Stairway to Heaven hike in Oahu

But about the back way…It’s a harder hike, it’s longer (9.3 miles of longer), but you don’t run the risk of running into law enforcement. Plus, isn’t it better to be rewarded for a tough hike?

So get yourself on the Moanalua Valley Trail. Steep, muddy, and with near-vertical sections to haul yourself up, this isn’t for the casual stroller—but it will get you the same views. If you need a guide—which I highly recommend for the back way—contact @mike.karas on Instagram who lives on Oahu and runs tours to the top every Saturday. Tell him Jeremy sent you!

Views along the back way to the top
You’ll catch views like this on the back way to the top

Once you get to the summit, you can walk partway down the forbidden steps themselves since they aren’t patrolled. Only the area around the bottom near the gate is guarded by security.

Though technically, once you step foot on the stairs, you’re trespassing, but let’s just pretend we didn’t know. Cool?

Difficulty: Hard
Length: 2.4 miles
Location: Honolulu

Final Words on the Best Hikes in Oahu

Hiking on Oahu island offers some spectacular encounters with Hawaii’s striking natural landscapes and diverse wildlife. The island is home to so many fantastic trails, but the ones discussed above are the best of the best. I hope this guide has proved useful and that the hikes treat you well.

Which of these hikes are you most looking forward to? Which do you think is the best hike in Oahu? Let us know in the comments!


  1. Please stop promoting illegal hikes. This list mentions the Tom Tom trail as one of the best but doesn’t mention the fact that it is 100% illegal. A hiker died back in 2015 falling 500 feet. It is illegal for a reason, it is dangerous. Even if you think you’re an experienced enough hiker do not attempt the Tom Tom trail. Police sit at the bottom and issue out citations daily to hikers. Its not worth the trouble!

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