8 Hikes To Do On Oahu / by Shane Henderson

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There are so many beautiful hikes on Oahu that it can be tough to know which to explore. But with three weeks on the island, we had plenty of time to try a whole bunch. We did most of the popular ones, with the notable exception of the infamous Stairway to Heaven. Although it looked amazing, there was a newspaper article the day we arrived about local authorities cracking down on trespassers. We just didn’t want to risk the hefty $900 fine which would put a big dent in our travel budget.  No worries though! All of the ones we did do were pretty spectacular and we loved them all. Here are 8 that we highly recommend.

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Maunawili Falls
One of the most-recommended waterfalls on the island (and for good reason. It is an awesome waterfall/swimming hole located at the end of a slippery, but relatively easy, 2-mile trail. The trail follows a stream through the lush jungle and takes you to a mossy, green hollow with a deep pool and a small falls cascading down. There are multiple spots for jumping off the rocks into the pool. The most popular one right next to the falls is only 7 or 8 ft high, but if you hike up the trail to the left you can jump off from 30 or 40 ft up. We watched some guy do it thinking he was gonna die for sure, but he was fine, so I guess the pool is pretty deep! This place can get pretty crowded so it's best to come on a weekday.

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Koko Head
Another very popular hike on the island. This “trail” is located just outside of Honolulu and is actually an old cable car track that goes 1,200 ft up to the summit. It is basically a huge staircase made up of tall, uneven steps. It doesn’t take that long to get to the top but, man, is it difficult. You are going straight up taking huge steps (your thighs will definitely start burning), and with no shade in sight the sun can be brutal. We thought we were in pretty good shape considering all the hiking we have been doing this past summer but we were huffing and puffing all the way up. We had to stop every 20 steps or so and watch as middle-aged locals jogged past us.  Ouch. The view at the top is pretty spectacular though, so if you are up for a workout, this one is worth it.

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Ka’au Crater
This is a relatively difficult, 5-mile hike that takes you through a variety of terrain to three waterfalls and up around a crater ridge. The first section goes up through a lush valley and, although beautiful, is one of the more slippery hikes that we have done. We went on a “dry” day and it was still really muddy throughout most of the hike. The first waterfall you reach is pretty cool. Although too shallow for swimming, it is located in a shady glen. Perfect for lunch or just to sit in for a moment to catch your breath. Full disclosure, we actually turned back after this as we were pretty wiped, but the rest of the trail sounded beautiful as well. Next time we will have to do the full loop.

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Olomana (Three Peaks)
This is a challenging 4.5-mile trail that is a lot of fun but definitely not for those afraid of heights! We only went to the first of the three peaks and even that involved some scrambling and walking near steep drop-offs. If you continue on to the other peaks there is a lot more cliff climbing and balancing on ridges with treacherous footing, supposedly. Even if you just make it to Peak 1 though, you will be rewarded with 360-degree views of the Windward side of the island. The trailhead for this one is located off the long driveway of a private golf course, so be sure to park around the corner from the golf course entrance and walk in.

Lanikai Pillbox
A short and very popular hike up to two pillboxes overlooking Lanikai Beach, this hike is best at sunrise. Bring a flashlight or headlamp and venture out before dawn, making sure to give your self about 30 or 45 minutes to reach the top. Once there, pick a spot on one of the pillboxes and watch as the sun rises over the ocean to illuminate the beautiful coastline. Although you certainly won’t have this spot to yourself (even on a weekday at 5 AM it gets pretty crowded), the phenomenal view makes it worth it.  Note: The trail entrance is on a private road so make sure to park around the corner and walk back to the trailhead. 

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Crouching Lion
Another short hike that is definitely a challenging one; this trail takes you straight up a mountain to a ridge overlooking the windward side of the island. There are a couple different “trails” leading up so it’s hard to know which one is exactly right. If you take the wrong one (like we did), you will have a pretty challenging ascent with some bush-wacking and rock climbing. Unreal Hawaii has some photos and instructions on where to go. Once at the top of the ridge, the views are pretty spectacular and there are couple rocky outcropping to climb up and sit on while you take it all in. For the more adventurous, you can keep following the trail up to the summit of Pu’Manamana, however that hike is much longer and pretty dangerous.

Kaena Point
Kaena Point is a bird sanctuary on the Western-most point on the island. You can technically get there from either the North Shore or the Leeward Side of the island but the walk from the North Shore is shorter so we recommend that. Drive all the way to the very end of the road in Mokuleia and you will find a gate with a parking area on the right. If you have a 4-wheel drive vehicle and a permit, you can actually go through the gate and keep driving down the rough dirt road. We had neither, so we parked and walked. Its about 2.5 miles from the parking area to the point and most of it is along a flat dirt road (so it makes for more of a walk than a hike). Once you reach the actual point, you can explore the sandy trails, bird watch, and take in the 180-degree views of the ocean and surrounding landscape. We recommend doing this hike in the late afternoon so that you can make it to the point for the amazing sunset. Just bring a flashlight so you aren’t walking back in the dark!

Laie Falls
Despite having easily our worst hiking conditions of the trip, this ended up being one of my favorite trails on the island. It is an 8-mile trek up along a ridge to a few different waterfalls. I loved it because there was a lot of unique terrain that made it feel very different then the other hikes we had done. After hiking out of some lush jungle, you go through a beautiful grove of Cook Pines and then up this long tunnel of brush until you come upon a series of steep waterfalls. Unfortunately, there were a couple things that made this hike pretty difficult for us. It rained a lot the night before our hike, so the falls at the end were raging torrents of muddy water and not particularly enjoyable to hang out at, the last section of the trail was very buggy because of all the fallen fruit, and on our way down we got caught in a storm and ended up soaking wet and freezing. Despite all that, I still really enjoyed this trail and would highly recommend it! Maybe just go on a drier day.