Hike Hawaii: Island of Oahu

Hike Hawaii: Island of Oahu

Alexandria Ugarte
Here is my ultimate guide to hiking the legal trails of Oahu. Now I've done my best to order these hikes from easiest to hardest considering elevation change, conditions, and climate. I say legal hikes because there are a good amount of illegal hikes on Oahu that have become very popular recently due to social media, but I only wish to recommend those that are open and maintained so that everyone using this resource can have a safe and amazing adventures while visiting this beautiful island. Beyond safety there is also the risk of large fines which will given to anyone caught hiking outside of public trails. In my own opinion there are no easy trails or walking trails on island as almost all trails are about elevation gain. Don't get me wrong Oahu is an excellent place for hikers, but probably best for those that consider themselves experienced hikers or are at least consider themselves athletic. I say this also because the hot climate and loose ground on much of these hikes makes for added challenge. My parents for example are now both over 60 and I would not take them on most of the hikes on Oahu and I likewise would have the same feeling about bringing children. A few important considerations when hiking on Oahu is to be mindful of preserving the trail and the environment. One rule of thumb is to stay on the trail, and I know that seems obvious but even stepping off the maintained trail a little bit or cutting corners on switch backs bear consequences; such as erosion and harm to plants and organisms that you may unknowingly step on. Another no brainer, but I still think the reminder is important, is to leave no trace. This means not leaving anything behind such as trash but also to not alter the natural environment like stacking rocks or messing with the foliage, beyond what is necessary to continue on the path. The opposite is also just as important, don't take anything with you from the environment like plants and rocks. I will try my best to include as much necessary information for these hikes as I can but it is always smart to be as well informed as possible before hiking somewhere new, so do your own research if you can and be well prepared for the weather, distance, and difficulty of each hike. State rescue personal often respond to hikers in distress here on Oahu and I would hate for anyone using my guide to face any sort of distress when they are supposed to be making fun memories. *I will be adding to this list as I do more hikes around the island*
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Level Easy

Likeke Falls Trailhead
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Nā Ala Hele Trail
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Manoa Falls
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1.7 mile out-and-back with an elevation gain of 633 feet. Mānoa Falls is probably Oahu's second best known trail and is a favorite for a reason. The falls at the end is great but this hike's true high point might be the amazing rainforest which you hike through to get to the falls. Wonder at the giant albizia's and mysterious banyans and you take in the fragrant air. The trail is mostly at a gentle slope if there hasn't been too much trail erosion from the rain. I think this is a good family friendly hike, just be sure to bring lots of water and be prepared to carry tired small children. I have seen some families attempting to bring strollers on the trail and I'll just say that, it's a mistake. The beginning of the trail may give the impression that a stroller can make it, but I assure you it is ill advised. There are not stairs exactly but at some parts there are large steps and the trail can be narrow at parts. Also to be expected is a crowd, this hike is quite popular and no one will appreciate having to scorch around your stroller. There is plenty of cover on this trail but still, don't skip the sunscreen and the bug repellent is a must. If there has been recent rain this trail can be real muddy, but the trade off is a more full waterfall. At the end there is a viewing area for the falls and signs all around warning to not cross the barrier. You will probably see many others ignoring the warnings of falling rocks, so just know you are taking your own life, and the lives of any children with you, in your hands if you choose to ignore the warnings. Another thing to know is that parking at the trail head costs $5 per car.
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Diamond Head Crater Trailhead
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1.8 mile out-and-back with an elevation gain of 452 feet. Oahu's most well known and highly trafficked hike hasn't become so popular for no good reason. One of Oahu's few hikes I consider an option for families and those who might only hike on occasion. There is still a good amount of elevation gain to this hike as you will begin inside the crater and hike up to its highest peak for a spectacular view of Honolulu and the ocean. There are stairs and tunnels on this hike as Diamond Head used to an army base and the trail was how servicemen accessed the pillbox look outs at the top. The Hawaiian place name for Diamond Head is Lē'ahi, which means tuna fin. You may notice when looking at Diamond Head from Waikiki that it does indeed look like a fish's fin surfacing from the water. One thing to make sure of is reserving your visit before hand on their website if you are a visitor as you will not be able to enter the monument otherwise. Parking costs $10 per car and entry is $5 per person.
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Makapu‘u Point Lighthouse Trail
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2.5 mile out-and-back trail with an elevation gain of 505 feet. Makapu'u Lighthouse trail is also what I would consider a family friendly trail. This might seem daunting to some but the entire trail is paved and safe. If you have the muscle it is also possible to push a stroller all the way up. This hike is at the far east point of the island and so is subject to a whole lot of sunshine and sometimes high wind. All hikes on island require water and sunblock but this hike doubly so. Don't underestimate the sun and heat on this trail as there is no cover and the pavement is asphalt. This can also be a good hike for dogs so long as they have plenty of water, stay on leash, and have protective footwear. Because of the trails popularity parking can be hard to get especially on the weekend, so I recommend going on a weekday and heading out early for a good spot. The drive out to the trail head from Waikiki is quite spectacular as well.
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Lanikai Pillbox Hike
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1 mile out-and-back but with an elevation gain of 406 feet. This iconic hike is great for those without mobility issues. Make no mistake you will need good knees and ankles to make it up to the pillboxes. Parking can be difficult around the trailhead and Bluestone, a residence, will tow your car if you park in front of them. I recommend not parking at all on Kaelepulu Dr and instead finding a spot on a side street. If there is no parking in the Lanikai neighborhood then you can try for parking at Kailua beach and consider the walk to the trail head just an extension of your hike. If you are up to turning your adventure up a notch and have head lamps then I really recommend hiking up for the sunrise. Just be sure to be respectful of residents and move quietly through the neighborhood during those early hours. Also the pillboxes have been recently reinforced so they are much safer to climb on and get that bucket list photo.
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Puʻu O Hulu (Pink Pillbox) Trailhead
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1.6 mile out-and-back with an elevation gain of 679 feet. The Pink Pillbox hike is very similar to its much more famous cousin Lanikai Pillbox but I've ranked it as slightly harder as it is a little longer. The trail condition is a bit better than Lanikai Pillbox though as it is less trafficked. This hike is also a bit of a drive out from Waikiki, it is 32 miles away or about 50 minutes without traffic. I do still very much recommend the hike as it will give you a chance to check out the West Side of the island and the pink pillbox, a breast cancer tribute, makes for great pictures. As the Pink Pillbox hike is on the West side of the island the summit makes for a great place to catch the sunset. I do recommend headlamps and caution when hiking in the dark. Another piece of advise is to not leave any valuables is your car at this trailhead because it is a known spot for car break-ins.
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Level Medium

Koko Head Trailhead Parking Lot
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Koko Head is semi-affectionately referred to as the stair master.
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Wiliwilinui Ridge Trail
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Kuliouou Ridge Trail
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4.7 mile out-and-back with an elevation gain of 1,650 feet. This is a great hike for those who want a challenge with a reward worth the payoff. This hike starts at the back of Kuli'ou'ou valley and ends at Kuli'ou'ou summit. This is a popular hike and there is often a crowd on the weekends. Most complete the hike in a little over three hours. The first part of the hike is switch backs through the forrest with plenty of sun cover until you make it up to the ridge proper. Then there are plenty of 360 views unless it's a cloudy day. Often with these ridge hikes on the East side of the island there will be visibility at the summit even if it is cloudy so don't be to discouraged if there isn't full sun. But if it's raining then I do not recommend any ridge hike as it will be to treacherous. There is plenty of parking in the neighborhood around the trail head, just remember to be respectful of residents and to not leave any valuables in your vehicle. You can definitely get an Uber out to the trail head but might have to wait around for an Uber heading back to town.
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Mau'umae Trailhead
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Level Hard

Kaʻau Crater Trail
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4.5 mile loop with an elevation gain of 1,939 feet. Now Ka'au Crater is a doozy of a hike for many reasons and the only reason I have not ranked it as the most difficult hike on my list is because there are a couple of routes to the top and it is possible to avoid some of its greatest hazards. You can either hike the trail as a loop or as an out and back. Ka'au Crater is possibly most memorable not for its view at the top, which is similar to other hikes such as Wiliwilinui and Kuliou'ou, but for its multiple waterfalls. The first waterfall on the trail has a good little swimming hole to enjoy, but the falls after pose a real challenge. This trail requires some climbing with ropes that have been installed along side the falls and can be quite dangerous. These ropes are only maintained by local hikers and it is up to your best judgement if they should be relied upon. After making it up all the falls you will ascend to the ridge of the crater where the trail can be very narrow with steep drops on either side. There is also some more spots with ropes to be used to climb up steep inclines, once again use your best judgement. The West side of the crater is especially treacherous so coming back on the East side is recommended. Then coming back down the ridge is a breeze compared to scaling waterfalls and risking the craters edge. To get to the top with less risk you can hike up the ridge and avoid the trail along the stream, just make sure you don't miss the turn off at about half a mile. Shoe spikes are recommended for this hike.
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Mt. Olomana Trail (Three Peaks)
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ABOUT THE AUTHOR
Alexandria Ugarte
Travel research and planning is my passion.
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