Top 5 Difficult Oahu Hikes

by Mariam Beard • Last Updated: September 2022

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Top 5 Difficult Hikes on Oahu

Are you looking for a challenge? If so, then you’ll want to check out these Top 5 Difficult Hikes on Oahu. These hikes are not for the faint of heart and I don’t recommend taking children on them.

For each hike, I’ll provide the name, a brief description, a 15-second clip of the terrain, and a link to a full video that I made. In the description boxes, I’ve also included links to government websites, AllTrails, and other resources that you might need within the YouTube video description boxes.

#1: Stairway to Heaven

Stairway to Heaven is one of my favorite hikes on the island. We went the back way to Stairway to Heaven, going the backway along Moanalua Valley Trail. The whole hike takes 8-10 hours, depending on the conditions. If you see any rain on the forecast, I would not do this hike. Near the end of the trail, there is some rope climbing and mud, so it can be very slippery. I recommend going on a dry day with at least three days of sunshine.

#2: Hawaii Loa Ridge Trail

My second favorite hike is the Hawaii Loa Ridge Trail. There are some restrictions for this trail, as you have to have a Hawaii driver’s license in order to access it. It is a gorgeous ridge trail and I recommend doing it on a very dry day. There are plenty of steps and incline, so make sure to bring plenty of water. It should take 5-6 hours to complete.

#3: Three Peaks (Olomana Trail)

Three Peaks, also known as Olomana Trail, is another great hike. We accessed the wrong trail at first, so make sure to watch the video for full instructions on how to get to the trail. You access this trail by going into the Royal Hawaiian Golf Course and walking about a mile on the paved trail. It is a very arduous hike and the first two peaks are as far as we went. Bring proper shoes with spikes, as it can be very slippery.

#4: Mount Olympus

Mount Olympus is a really cool trail to start off with. You start off in a park area and then go through a little bit of the ridgeline. At the very end, there is an open summit area with views of the cityscape, mountains, and ocean. It is a very taxing hike, as it is almost all incline. Bring plenty of water, as it should take 5-6 hours to complete.

#5: Koko Head Crater

Koko Head Crater is a short hike if you want a quick stair workout for the day. The hike should take 1-2 hours to complete and almost the entire thing is inclined. Make sure to bring plenty of water and do this early in the day.

My Favorites

These are my Top 5 Difficult Hikes on Oahu. I hope this post has given you an idea of what to expect from each hike and that you’ll be able to find the perfect hike for you. Make sure to check the weather report and bring the proper gear before heading out. Happy hiking!


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Aloha! I'm Mariam.

I'm an Oahu resident sharing my adventures here in Hawaii to help take the guesswork out of planning your trip to Hawaii.

I've worked full-time as a concierge for a decade and have planned thousands of itineraries for travelers like you!


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