Olomana Hiking Trail (Three Peaks)

Difficulty Level: Hard
Trail Distance: 4.5 Miles

Without a doubt one of the best places to hike in Oahu is, the Olomana hiking trail.

Also known as Three Peaks, Olomana is a rigorous out and back style trail that takes around 2.5 hours to 7 hours to complete depending on which peak you reach.

Each peak has own distinctive difficulty level with the first peak being the easiest, as they progress to become increasingly more difficult as make your way along the trail.

The third and final peak is perfect for daredevils, looking for their daily dose of adrenaline as you attempt to vertically scale the narrow ridge by means of some sketchy timeworn hiking rope that is stapled into the side of the cliff.

Though this particular Oahu hike is one of the most famous on the island, it is also one of the top 3 most dangerous in my opinion.

However, a majority of the dangerous moments occur once you get past the first peak.

In which case, lucky for most non-daring hikers this is where some of the most impressive landscape pictures of Olomana are taken.

Nonetheless, genuine thrill seekers will not be able to deny the temptation to continue onward toward the more dangerous sections of Three Peaks.

Suggested Blog: Three Peaks Hike | The Most Underrated Trail In Oahu

Stairway To Heaven

Difficulty Level: Hard
Trail Distance: 3 Miles

Boasting an impressive 3,922 stair climb into clouds above Oahu, The Stairway to Heaven will always be known as one of the best hikes on Oahu.

The Stairway to Heaven alternatively known as the Haiku Stairs, unlike the rest of the Oahu hikes left on this list, presents one of the greatest challenges to those who dare to climb it.

Amidst the massive Koolau Mountain Range, The Stairs were built all the way back in 1942 as the U.S government assembled a top-secret military base called the Haiku radio station.

However, the stairs were officially decommissioned sometime in the 1950s, and have since then been left in a pretty bad state after not being maintained for all those years.

A particularly bad storm completely took out a whole section of the stairs, requiring daring hikers to navigate around this potentially deadly obstacle.

On occasion hikers will attempt to climb the menacing Stairway To Heaven, however, are reportedly unable to complete the hike due to injury or fear to move resulting in the desperate need of an air evacuation.

These rising safety concerns led the Hawaiian government to officially close the stairs to the public in 1987.

Although the deteriorating condition of the stairs is one of the reasons the Haiku Stairs is considered one of the most difficult hikes on Oahu, infiltration past the stationed security guard along with sporadic police presence is what creates the biggest challenge.

Not to mention that when caught attempting the trail, Oahu hikers have seen fines of $1000 or more and on a few occasions even been arrested.

In case you are unaware a fine of $1000 is no slap on the wrist and is in fact, considered a felony, charge which is no laughing matter.

As truly one of the most dangerous hiking trails on Oahu, anyone who successfully climbs the menacing Stairway To Heaven certainly deserves some applause.

Suggested Blog: Stairway To Heaven Hawaii {The Certified Haiku Stairs 2019 Guide}

Crouching Lion Hike

Difficulty Level: Moderate
Trail Distance: .4 - 4 Miles

Regarded as one of the top 10 most popular hikes on Oahu, Crouching Lion is a relatively short but challenging trek up to one of the most stunning vistas on the entire island.

Though the trek up should only take around 30 -45 minutes, I do use the term “trek” rather loosely, considering that a majority of the trail consists of an almost vertical climb.

Assisted by previously tied hiking ropes and tree stumps, the trail up this crazy Oahu hike, doesn’t come without its fair share of challenging moments.

However, don’t worry because like most hikes in Oahu, the ends well justify the means and Crouching Lion definitely abides by that statement.

The panoramic views over Kahana Bay will leave you utterly amazed as you gaze out to one of the islands most remarkable viewpoints.

In addition to this, the hike does go on for other several miles, however a majority of hikers quite satisfied after hiking the first section of the trail.

Suggested Blog: The Ultimate Guide To Finding The Crouching Lion Hike In Oahu

Pali Notches

Difficulty Level: Extremely Hard
Trail Distance: .7 Miles

Giving you vertigo for the next week, Pali Notches has some of the most death-defying moments in comparison to the other Oahu hikes on this list.

Well surpassing The Stairway To Heaven and Three Peaks as the most dangerous hikes on Oahu, Pali Notches is a trail that should only be attempted by the most experienced of hikers.

Successfully navigating this trail is no small feat, especially considering that parts of the trail involve climbing up a vertical rock where one wrong move in either direction could result in a tragic death.

In addition to this, hikers are forced to navigate along the narrowest of mountain ridges with steep and unforgiving cliffs on both sides waiting for one strong gust of wind or one bad step, so they can potentially claim yet another victim.

Pro Tip

Please only attempt this hike with legitimate hiking shoes because there are literally parts of the trail where you are dangling on cliffs edge where the only thing keeping you from falling is someone else’s hiking rope.

Tom Tom Trail

Difficulty Level: Hard
Trail Distance: 6.6 Miles

Have you ever even heard of the Tom Tom Trail… probably not.

For some strange reason, this is one of the least hiked trails on Oahu even though its views are some of the most phenomenal!

However, consider its relative unpopularity a blessing because with any luck at all, you will be the only ones on the entire trail!  Which is something very unique on this island considering how overcrowded the rest of the Oahu hikes are.

Another thing to love about the Tom Tom trail is that even though it is a whopping 6.6 miles long trek, you can experience all the breathtaking beauty of it after just the first 30 minutes.

As a matter of fact, a majority of hikers don’t even bother completing the trail given quality of views from very early on

Additionally, given how close it is to the Makapu’u Lighthouse, the two of these top Oahu bucket list items can be crossed off on the same day!

Considering all of this, it’s almost impossible not to think of this place as one of the most underrated trails on Oahu.

Manoa Falls Trail

Difficulty Level: Easy
Trail Distance: 1.5 Miles

As far as Oahu waterfall hikes go, there are few and far between on this island.

Which is why the Manoa Falls trail is such a popular attraction on the island.

However, to call this trail a hike is a bit of a stretch.

Although it has some slippery and tedious moments, all things considered, it’s more of leisurely stroll through the jungle that even most physically unfit of hikers could complete.

Which is not the case for the majority other hiking trails on this list.

However, just because this is one of the easiest hikes on Oahu, doesn’t mean it is an unrewarding trail. In fact, views along the winding rainforest trail are quite mesmerizing and even better once you reach the charming waterfall at the end.

Though, you should be advised not to swim in the pool below the falls because it contains a very harmful bacteria, that is rumored to well…eat your brain or something.

Usually, we feel rules are meant to broken, however when it involves Hawaiian brain consuming bacteria, that’s usually where we draw the line.

Nonetheless, if you have been in desperate need of a recovery day, but still want a fun adventure, then Manoa Waterfall is just the thing for you.

Suggested Blog: The Ultimate Manoa Falls Trail Guide To This Stunning Oahu Waterfall

Seven Falls Waterfall Trail

Difficulty Level: Hard
Trail Distance: 2.1 Miles

This is one of the lesser known hikes in Oahu and very popular among the locals.

Similar to Tom Tom Trail, Seven Falls is unlikely to have many other people on the trail with you so don’t expect other hiker to lead the way.

Considering that there aren’t many hikes on Oahu with waterfalls, consider this one a blessing because it graces you with 7!

However, don’t expect a leisurely stroll through the jungle along the Seven Falls Waterfall Trail. In true Tarzan fashion, expect to do some rope climbing as you have to scale these waterfalls in order to successfully complete the trail.

Not to mention some of these waterfalls are around 50 ft high, so you better put on your big boy pants for this particular Oahu hike.

Diamond Head Trail

Difficulty Level: Easy
Trail Distance: 1.8 Miles

Possibly the most popular out of all of the Oahu hikes, The Diamond Head Trail offers a rewarding 360-degree panoramic view once you reach the top of the volcanic Crater.

Diamond Head trail is a very simple out and back trail that takes around 30 minutes to an hour to hike up depending on your fitness level.

Unlike most of the other top hikes in Oahu, the Diamond Head hiking trail is within the Diamond Head national park.

Therefore, the park has set opening and closing times from 6 a.m – 6 p.m, however, the last entrance into the park is at 4:30 p.m.

Koko Head Trail

Difficulty Level: Moderate
Trail Distance: 1.8 Miles

Anyone who regularly uses the Stairmaster at the gym will find this popular Oahu hike exceptionally easy.

The hike up this distinctive 1000 plus step trail along an old abandoned railroad track, is one of the most famous things to do in Hawaii.

In fact, many Hawaiian locals regularly hike this trail in the morning before they begin work.

Heck, I’d probably become find time for a sunrise workout too if it meant I could continuously hike one best trails in Oahu every morning.

Though Koko Head doesn’t hold many surprises or death-defying moments like other Oahu trails, the remarkable views of the east Honolulu shoreline are guaranteed to leave you with some long-lasting memories.

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