Top 5 Hikes Loved by Locals on Oahu, Hawaii

With breathtaking views of wandering beaches and vast bays, the Lanikai Pillbox Hike has earned its reputation as one of the most popular, rewarding, and easy hikes on Oahu for good reason. Stretching up the mountains and ridges of the island’s windward side, this short and steep trail rewards hikers with an unforgettable experience that you won’t be able to find anywhere else.

The Lanikai Pillbox Hike starts at the end of a residential street. About a quarter mile in, along a relatively steep trail, you get to the first pillbox. A pillbox is a block-shaped fort that the military uses as a guard post. There are a handful around Oahu and I love the bird’s-eye view of the surrounding area they offer. Once you head along the Ka’iwa Ridge, you can see wonderful views of the Hawaiian waters. I am always enchanted by the sounds of the waves crashing and the wind whistling. The trail is steep, but short, making it perfect for a sunrise or a sunset hike. If you are looking for an easy hike on Oahu to end your afternoon, this is where I would go.

The hike’s notorious “pillboxes” — abandoned military towers once used as guard posts — offer vantage points of the surrounding area. Run up, enjoy the scenery and then head back to the beach or into Kailua for a nice dinner or swim. Kailua used to be a quiet town on the edge of Hawaii, but in recent years it has transformed into a bustling beach town. The beaches of Kailua can be seen on the front pages of travel magazines, and for the right reasons. After a hike or a swim, people get hungry, so Kailua grew it’s restaurant scene to fill the bellies of avid outdoors people.

The Koko Crater Trail, better known as the Koko Crater Stairs, is a hike of endurance and mental strength. With over 1,000 steps over about one mile, each step is more challenging than the last. At the same time, the hike is one of the most rewarding ones on the island of Oahu. The panoramic views from the Kokohead Lookout are one reward, but the second is the feeling of accomplishment and strength you get to the top. You feel invincible, and sometimes when I need a confidence boost, this is the hike I head to.

Like I mentioned above with the Lanikai Pillbox Hike, the military created pillbox bunkers during World War II, but then they needed a way to haul cargo up the mountains, so they created the Koko Crater Tramway. The leftover rails are used as hiking stairs to reach the top of the military bunkers and the ridgeline. After parking in the Koko Head District Park, head towards the trail which is easily definable and start making your way up. After the first 100 steps, you will start to see Hanauma Bay and the Port Lock Peninsula. Keep making your way up, and eventually be rewarded with a beautiful lookout over the Koko Crater.

The majority of the stairs on the Koko Crater Trail are much longer and taller than your average house stairs, so while you might think, “it’s just stairs it can’t be that hard,” trust me it can. Even the flat section poses a challenge as it is a bridge with a 40-foot drop below. If you have a fear of heights, there is an alternative route you can take.

You need lots of water, and avoid doing it in the middle of the day when the sun is the hottest. If you do go for sunset, don’t forget your headlamp! The confidence boost you get once you are at the top is like no other. If the Koko Head Stairs are just far too busy, but you still want to get up close and personal with the crater, check out the Koko Crater Rim Trail.

If you are looking for the most classic jungle hike on Oahu that also has enchanting waterfalls, in my opinion, the Ka’au Crater trail is it. The hike starts in a small residential area, but don’t be fooled because immediately you drop into the jungle following a stream. The stream is surrounded by trees taller than buildings and vines dangling from every branch. Nature hugs you during this hike, and sunlight peaks through the dense flora every once in a while. You carry on following the stream and a water pipe until you reach your first waterfall. A perfect place to eat your lunch, and for those daring few a great place to jump into the water.

The hike continues through the dense forest. A little bit of scrambling and assistance of ropes to get over a few tricky sections is necessary, but soon enough you reach your second waterfall. It is completely different from the first and comes at you out of nowhere. After a quick climb up the second waterfall, you will reach yet another beautiful waterfall nestled among the rocks. The hike gets more technical; scrambling up the sides of the waterfall can get slippery and difficult. At the top take a close look at Ka’au Crater because it is a view like nothing else, truly majestic. Grab a bite and then continue your journey down a ridge completing your loop and your hike.

I love this hike because it is exciting. Many other hikes, while incredibly beautiful, offer the same kind of scenery over and over again. This hike is full of surprises — waterfall after waterfall, the next one different and more interesting than the last. After all of scrambling up, you don’t take the same way down, rather you follow a ridge which offers completely different scenery. There aren’t that many people on the trail, and it’s a real treat to be in the jungle alone.

The Olomana Trail, also known as the “Three Peaks’ hike, is my favorite hike on Oahu, traversing the narrow Olomana, Paku’i, and Ahiki peaks. I like to think of this hike as three different challenges in one. As you go up in elevation, there’s more scrambling and the trail gets more technical. First, you start off in the jungle, so be prepared for the usual mud. Then, to the first peak it’s a cardio workout. At the top of the first peak, you get views of the windward side of the island, where Lanikai Beach sits. This is where the feeling of accomplishment starts to creep in.

The hike to the second peak is just a short 10 minutes, but it is aggressive. 80% of people get to the second peak, turn around, and go back. I think it’s because they’ve felt the sense of accomplishment they were looking for and they know it only gets harder from here. The third peak looks intimidating from the second one, and in many ways it is.

The third peak is the most difficult and also the most technical. You have to drop down with the help of ropes from the second peak. To get to the second peak after the drop, you scale up the side of it. It can get super narrow and the rock is often crumbly. The third peak is intimidating, but I don’t want that to discourage anyone because the little extra push you might need to give your legs is 100% worth it! You can see all the way to Manana Island from the top.. It is my perfect little euphoria up there. Now the challenge, yet again, is that you have to go back the same way you came. That means going down the third peak, up towards the second one, back down the first one, and finally all the way to your car.

It might seem daunting, but this hike is one of my personal favorites. Many times I go up to the third peak to watch the sunrise. I wouldn’t recommend doing that for first timers as hiking in the dark or half-lit light takes experience. This isn’t the hike to try out this skill for the first time. I cannot pinpoint how this hike makes me feel, but I think it should be clear that I think it’s pretty amazing. I have returned time and time again and will continue to come back.

Stairway to Heaven (AKA the Haiku Stairs) is one of the most photographed trails in all of Hawaii. Unfortunately, hiking the traditional stairway route is illegal. The back route up via the Moanalua Valley Trail (not hiking up the actual stairs) does lead you to the Haiku Stairs viewpoint, although it’s a much more challenging route. This is a famous destination so I felt like it needed to be included, however it is not my favorite trail, and I avoid it because of the crowds. Please note that Moanalua Valley to Stairway to Heaven is a very sensitive trail that that is prone to erosion and for that reason I recommend skipping it, but the history here is very complex and fascinating.

Originally built in 1942 by the U.S as a facility for transmitting radio signals to ships in the Pacific, 3,922 stairs make the way up a mountain ridge to form the Stairway to Heaven. It is a trail with a fascinating story that leads to some of the best views of the island. Unfortunately, access to the stairs has been prohibited since 1987 for safety reasons. The Stairway to Heaven has since become a heated topic, and while locals hikers who have been using the stairs long before they were closed continue to do so, it remains illegal and is not recommended.

There are talks about tearing down the stairs, which by some estimates would be more costly than simply repairing them and opening them to the public. My personal opinion is that the stairs should be repaired and opened to the public, possibly for a small fee. The situation is escalating and changing at all times. No matter what your stance on this issue is, the hike remains illegal. If you are a first time visitor, I advise you to avoid the $1000 fine, a run in with the cops, and disturbing the local people. When the cops are called, when people jump over the fence, they disrupt Hawaiian neighborhoods, so please be respectful of these communities.

The alternative way to the viewpoint begins at the Moanalua Valley trailhead and is a 9.3-mile round trip that will take you all day to hike out and back. It is a tough trek since there are multiple sections with rope climbs and very steep ascents. Hiking this back route will take you to the same exact viewpoint at the top as the actual stairs would, but please note, the back way is not really permitted either. At one point on the trail, close to the stairs, police can fine you even if you are not on the steps because you are trespassing on the land. So even on this back route, you need to know the rules and you really should follow them. I’m of the opinion that even though this might be one of Oahu’s best hikes, you should consider skipping it for now until the issue is resolved.

If you’re planning an Oahu hiking trip, here are a few things to keep in mind:

What is the best time of the year to hike on Oahu?

While the weather permits you to hike on Oahu year-round, the best time to visit Oahu is from mid-April to early June or between September and mid-December. These are the shoulder seasons, meaning less crowds and cheaper airfare and accomodations.

What is the easiest hike on Oahu?

Lanikai Pillbox Hike is, in my opinion, the easiest Oahu hike. If you have time only for one outing on the trails or don’t want to break too much of a sweat, head to Lanikai Pillbox. It will give you a little bit of Hawaiian history, great views of the surrounding nature, and a great sport for a post hike bite.

What is the hardest hike on Oahu?

The Koko Crater and The Olomana Trail are among the hardest hikes on the island. The Koko Crater Trail is difficult because it requires a significant amount of endurance. Don’t be fooled by the shortness of the hike, because it is steep and challenging. The Olomana Trail is for advanced hikers due to the increasing difficulty as you gain elevation. It is a hike that requires technical skill and endurance.

What is the longest hike on Oahu?

The Kawailoa Trail is the longest hike on Oahu at 9.4 miles. The trail is located near Haleiwa and it is a muddy and long path to the Koʻolau Summit. The hike takes about eight hours and consists of 1,408 feet of elevation gain.

How many hikes are on Oahu?

Oahu has upwards of 236 hiking trails scattered throughout the island. Trails range from easy to advanced so everyone can find something they like. There are trails for young families, families that can take on harder terrain, super fit trail runners who want to test their endurance, people with furry friends (aka pets), and more.

Does Oahu have good hiking?

Oahu has the best hiking of all of the Hawaian islands, hands down. Oahu’s hiking trails cover two volcanic mountain ranges that border the island. There are trails that encounter waterfalls, go through the rainforest, go on top of World War II pillboxes, or follow the coastal ridgeline. Overall, Oahu offers a range of terrain for every skill level that is hard to find on any other island.

Do you need a guide for Oahu hiking?

There are so many trails on Oahu that there’s something to suit all skill levels. Depending on your level of experience, with the right planning and info, you may feel comfortable hiking on your own. There are certainly enough options to explore. But, if you’re looking for a new challenge or you want to learn more about the local history and biodiversity, hiking with a guide is the way to go. Not only will you be shown the best spots, you’ll be hiking with a person who can ensure safety while introducing you to the local Oahu culture, and you can leave all the planning to them so you have more time to enjoy your trip.

Are you ready to head out hiking on Oahu with a guide? Check out some of the trails offered or set your sights on a Hawaii surfing adventure. One thing’s for certain on Oahu, adventure awaits!