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Kyle Jenkins | 10.17.2017

When the Hawaiian Islands come to mind, we tend to think of blue water, palm trees, and white sandy beaches. An underappreciated side of the island chain lies further inland under the thick jungle canopy, among the tropical birds and the many waterfalls. Hiking here is starting to really catch on as more people are realizing what great new adventures can be found on these islands. Let's take a look at some of the best trails you can experience on the capitol island of O'ahu and the many diverse hikes it offers.

Mānoa Falls Hike

This is one of the most popular hikes on O'ahu thanks to its short length and great array of trees, plants and flowers. The tall and pretty waterfall at the end has a small pool to take a crouching dip in, but be ready for heavy crowds.

Maunawili Falls Hike

This popular and muddy trail near Kailua leads you to a large swimming pool that is commonly shared by locals and tourists alike. Keep an ear out for the many colorful tropical birds in the canopy and the crayfish in the water.

Lanikai Pillbox Trail

Another incredibly popular trail that is relatively short but steep. The views are out of this world and look down onto one of the prettiest beaches in the U.S. Lanikai Beach and the Mokulua Islands below are straight out of a magazine cover, and the hike is a must-do while on eastern O'ahu.

Diamond Head Crater

This stair-heavy hike is crazy busy, but it also has some of the best views of Honolulu you can find. Famous for its leftover World War II ruins and quick elevation gains, it's worth trying out once, but hopefully on a weekday morning.

Pu'u Ma'eli'eli Trail

The easy-to-miss trailhead heads a little over a mile up the east side of the island on a relatively easy trail with great ocean and mountain views. You can see Chinaman's Hat and Kualoa Beach in the distance from the peak as well as the Ko'olau Mountains on the way back down.

Koko Head Stairs + Koko Tramway

Koko Head sticks out of the landscape like a sore thumb covered in dry vegetation on the southeast point of O'ahu. A historic tramway provides a steady climb up this unusual mound toward 360-degree views at the top. The 1,200-foot climb is commonly used as a morning workout for many local residents.

Ka'au Crater Hike

This hike-in only route is 3 miles each way, but it does gain nearly 2,000 feet as you make your way up to the spectacular views of downtown Honolulu below. The large and undeveloped Ka'au crater sits below and gives a nice break to the sprawling metropolis of the capitol city. There are waterfalls and a few sketchy sections where ropes are used.

Kolowalu Trail

This short but very steep hike gives you incredible views down valley toward Honolulu. The lush hillsides of Manoa tends to have great songbirds and flowers in its bamboo, guava and eucalyptus trees. There are great views when the city lights up, but be careful on the descent.

Kuli'ou'ou Ridge

This steep trail takes you to a lookout that gives you panoramic views of east O'ahu from atop some of the most vertical mountains you will ever see. Starting on one side of the Ko'olau Mountains you ascend the switchbacks to get an entirely new view over the other side of the island. This ridge is a rare treat and a good place to get away from crowds.

Aiea Loop Trail

This popular trail gives you great views up a jungle-covered canyon without the difficulty or danger of many of the others on this list. This hike is just under 5 miles, there are no heavy switchbacks, and you still get a great tropical experience. The Aiea Loop may be short on sweeping views, but it is heavy on great interaction with nature.

Olomana (Three Peaks) Trail

The hike to the first peak commonly done by many people on the windward side of the island. It involves some light scrambling and rope-assisted climbing, but it rewards you with great views of Kailua below. The second and third peaks are dangerous hikes that have claimed too many young lives over the years. Use extreme caution

Pu'u Manamana Turnover Trail

This is one of the riskiest trails to attempt in the islands due to its relatively easy access to razor thin peak traverses. One-thousand-foot cliffs on each side are topped with craggy and crumbly basalt lava rock. The views of the Kahana Valley are amazing, and so are the bragging rights.

Konahuanui Summit / K2 via Pu'u Ohia

Another stunning peak hike, this 6-mile round-trip hike takes you up the second tallest mountain in the Ko'olau Range with some of the best views on the island. Start out from the top of Tantalus and hike into the clouds.

Kulana'ahane Trail

This 10 mile beast of a round trip gives you stunning views of the curtain of stone called the Ko'olau Mountains. You are allowed to backcountry camp with permits while checking out the waterfalls, stream crossings and unparalleled sights of windward O'ahu.

Mount Ka'ala

The highest peak on O'ahu, the steep trail gains 3,500 feet in just over 4 miles. This dangerous and rugged hike gives you views of the O'ahu's North and South shores, an uncommon treat assuming the clouds are not covering the peaks.

Haiku Stairs, also known as the Stairway to Heaven

This illegal yet somehow still ultra-famous hike takes you up and down a ridiculously steep set of stairs that were originally built to man and operate a lookout during World War II. Social media has made this place famous, but a major landslide has destroyed many of the stairs. People attempt to avoid the security gaurds by starting at the top and working their way down to the best views, but hikers risk tickets, fines and trespassing charges. 


Please keep in mind that some of the hikes here can be pretty dangerous due to the consistent rainfall and brittle, flaky volcanic rock that dominates the terrain. Injuries can result from falls off of steep cliffs or from miniature landslides caused by saturated ground that gives way beneath people's feet. Be careful and allow the terrain to dry out before attempting certain trails.


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