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5 Challenging Hikes on Oahu

a person standing on a lush green hillside

Hawaii can offer a great variety of hikes: family and dog-friendly hikes, the trails with the most beautiful views, and of course hikes for adrenaline junkies! But please be sure to stay focused, smart, and prepared for the challenging hikes—they can be quite dangerous and exhausting. In this article, you will find our 5 favorite challenging hikes on Oahu! “Challenging” means you should be in above-average athletic shape, have previous hiking experience, and be ready to spend most of the day on the trail.

1. Olomana/Three picks

Olomana hike is an adrenaline junkie’s dream! There are a dozen different spots along the trail that have ropes. Sometimes they’re unnecessary. BUT sometimes your life depends on it!

In order to accomplish all three picks, you should be in pretty good shape. An elevation gain of more than 1,600 feet, and you’re going to be required to balance, hoist yourself up and down the ropes, and do a little rock climbing. The view after the first pick is breathtaking though! One of the most popular Hawaii hiking pictures was made there!

a person standing on a lush green hillside
Three Picks Hike Oahu

Tips and important information: Hiking shoes, plenty of water, and a clear mind are must-haves during the hike. Think several times before going to complete the third pick-it can be really dangerous!

2. Koko Head

Not as challenging and dangerous as a previous hike however better and more difficult than a gym workout. You will definitely feel the muscles several days after the hike. This trail will test your endurance and strength with every step up the mountain and as you stride, over 1,000 steps you will reach the top of this amazing hike! We love the hike for the opportunity to meet like-minded people on the way who loves challenges and good workouts.

a woman standing in front of water
Koko Head Hike

Tips and important information: We do not recommend taking dogs and kids. Since the hike consists of some of the dangerous parts. Make sure to take sunscreen, a hat and water – there is no shade on the trail. Better to do the hike in the early morning or sunset to catch the amazing view.

3. Mount Olympus Awaawaloa via Wa’ahila Ridge Trail

The Mount Olympus Hike is a slippery, muddy adventure up to the Koolau Summit Trail on Oahu. While not the most extreme hike on the island, this one will challenge you with some solid inclines and a few steep sections requiring a rope. Views from the top extend to both sides of the island and make for a beautiful reward at the summit.

a large mountain in the background

Tips and important information: Be prepared to get dirty on the way. We recommend bringing gloves for the rope sections. As usual water, hiking shoes, and courage are required!

4. Moanalua/Kamananui Valley Trail

The Moanalua Valley Trail to Haiku stairs hiking route is one of the most adventurous hikes on Oahu. The hike follows the Moanalua Valley Trail before connecting up the Moanalua Middle Ridge, which is the legal ‘backway’ to the Stairway to Heaven (Haiku Stairs) satellite summit.

Overall the hike up the Kamananui Valley Trail is not difficult, but still long enough to provide a good workout with an amazing view as a reward.

a view of the side of a mountain
5 Challenging Hikes on Oahu

Tips and important information: If it has rained any time in the days before your hike, the trail is very slippery and muddy. A headlamp, rain jacket, water, and good hiking boots or shoes are the three main pieces of gear you need.

5. Mount Kaala Trail

Mount Ka’ala is a tough climb with 3,500 feet of elevation gain. We recommend it only for advanced hikers. There are slippery conditions, steep drop-offs, boulders to climb, and ropes. From above you’ll see the Waianae Valley, a beautiful place surrounded by jagged green ridges and the ocean in the distance.

Tips and important information: Be prepared to get dirty on the way. It is also important to bring gloves for the rope sections as well as water and hiking boots.