The Maili Pillbox Hike is an adventurous, fun, and less traveled Oahu hike located on the West Side, also known as the Leeward Side of Oahu. Similar to the Lanikai Pillbox Hike, which is one of the most popular trails on the island with 2 bunkers to reach, the Maili hiking trail winds up higher on the mountain side with incredible views, and not just 2 but 4 military pillboxes you can explore on your way to the top. This Oahu hike is considered one of the top 5 off the beaten path moderate hikes that many hikers can enjoy.
While there are not many Oahu hiking trails on the West Side of the island, Maili Pillbox hike is a really cool hike that is just 10 minutes up the freeway from the Ko’olina Lagoons.
A series of military pillbox bunkers pillboxes were built in various spots around Oahu, including the Maili area of Waianae. Some areas like Lanikai on the Windward side and Ehukai in the North Shore have 2 pillboxes that you can hike up to, but Maili has 4 distinctively different military pillboxes along the ridge that you can hike up to and take in panoramic views
All 4 pillboxes line up along the same ridge and are relatively close to each other. There’s even a 5th pillbox that is mainly in ruins, but still fun to see while you’re on top of the ridge.
Once you have parked, geared up, and are ready to hike, proceed to the unmarked Oahu hiking trail that should be clearly visible from the street, about a ¼ mile up Kaukama Rd.
The Maili Pillbox Trail starts off on a stone pathway that leads gradually up the hill. You might question it because there are no signs in the area, but there are usually a few cars parked along the street.
The path is pretty clear and distinctive with a clearing into the hillside with a stone pathway that starts off with a slight tilt…maybe from the hillside shifting over the years. As you get started, look up and you should see one or two of the pillboxes perched up top.
As you walk up the hill, the trail turns into small boulder-sized steps that continue upward along the mountain. The trail is lined by high grass, bushes and trees.
You only have to walk up 100 to 200 feet before a spectacular panorama of Waianae Valley and the Pacific Ocean come into view. And you will be treated to these incredible views on this Oahu trail all the way up.
Once you get to the top of the stone steps, the Maili Pillbox Trail starts to smooth out into a hard packed dirt path, and continues to travel up on a steady slope along switchback trails to help make the climb a little easier to trek.
You will also appreciate the many different perspective views this Oahu hike provides each time you trek one of the switchback turns.
Don’t be surprised to see lots of different species of birds flocking the area…it almost feels like a bird sanctuary. There isn't a lot of shade on this hike, but there are some small dead trees along the way.
Their worn trunks and branches have faded into a silver gray, and they dot the mountainside like sculptures that nature has planted there.
Watch your footing as you’ll travel though a long patch of small, uneven rocks and boulders, some of which can be loose. It might not be a challenge for most, but some people could be prone to falling and could get hurt on the trail. Hike at your own pace, be careful, and be mindful of your steps.
You will have plenty of areas where you can pause to take breaks and enjoy the scenery. The expansive views continue to change in all directions the higher you hike along the switchback trails.
At one point you should be able to see all the way to Makaha, and deep into Waianae Valley. Remember it’s a longer climb up to the top versus Lanikai Pillbox Hike, so take it slow and enjoy.
The last long stretch of the Maili Pillbox Trail is quite rewarding, with unobstructed views of the beautiful pristine coast, the Waianae mountain range in the distance over near Makaha, and the local community homes in the valley below.
Close to the top, the first pillbox will come into view, as well as some old military equipment, and a couple of old bunkers that are in ruins now.
Reach the top of the ridge and you will be rewarded with some of the best views of the Pacific Ocean, and the south side, also known as the Leeward coast of Oahu, which the
mountain was blocking on your way up. This is known to be the sunny and dry part of the island.
There are 4 intact pillboxes that you can explore. Each one differs slightly in setting,
character, views, and graffiti artwork!
The first 2 pillboxes should be in plain sight at this point. The first Maili Pillbox is one of my favorites.
It might look a little plain on the outside with four intact walls, a roof, an open doorway, and a long, rectangular window where the soldiers would peer out and keep watch. And has the best views in my opinion!
Step inside and be amazed by some of the murals that now cover the interior walls. The view from the window is one of the best of the four in my opinion so enjoy!
Just a few more steps up the hill, not more than 100 feet away, you will come upon the second Maili Pillbox. Similar to the first pillbox, this one is pretty plain on the outside but a tiny bit larger in size.
The artwork inside is colorful to say the least, but more in graffiti form with people signing their names and fancy tags on the walls. The view from this pillbox are equally nice and similar to the first pillbox.
It’s also common to see hikers climbing onto the roof of all 4 structures, for the novelty, exploration, getting a better view, and perhaps feeling on top of the world.
We cannot recommend climbing onto the roofs of these bunkers as it takes a little skill getting up and off of them. You can easily fall and get injured since there are no ladders, support, or guard rails to hold onto or protect you from falling off. Take caution and proceed at your own risk.
The same trail connects all 4 Maili Pillboxes, and walking up another 100 feet will get you to the third pillbox. This Maili pillbox is by far the most popular, and distinctive from the others, as it has been painted pink inside and out.
To our knowledge, it was purposely colored pink for women's breast cancer awareness, and a large black ribbon was painted on one of the sides. To say the least, it gets the attention of everyone who hikes this Oahu trail.
Like I mentioned, the interior is painted pink as well, but unfortunately less impressive than the first two, as it has been vandalized over the years with amateur style graffiti…mostly people tagging their name on the wall. Pillbox artwork around the island usually doesn’t last long as other artists have new creative visions to display.
You can only hope it’s tasteful and inspiring. Hopefully it won’t be long before the inside of the Pink Pillbox will be repurposed to something more meaningful.
Near the Pink Pillbox is another viewing pillbox that is pretty much in ruins. It sits on the north side vs the ocean. And while the walls still remain, the roof is gone with not much left to see...yet it overlooks the beautiful Waianae Valley.
The fourth Maili Pillbox sits a good 300 feet away. And while all hiking trails come with some risks, trekking to this pillbox comes with extra risk, as it travels along the thin ridge.
This stretch of trail is narrow and has a few obstacle rocks you will need to step over. We cannot recommend traveling to this fourth pillbox, for reasons of falling with injury, and should only do so on your own accord.
Here’s what you can expect if you do make the journey, or would just like to know that is there. If you do decide to continue onward to this structure, be extremely careful when crossing the ridge. It can get windy up there and make it harder or more challenging to travel along.
The 4th pillbox is by far the largest of the four and has a much different appearance than the others. It might have been used for more than just observation like the others. This one is nestled a little more into the hillside, which makes it easier to climb onto the long flat roof.
There is also an attached metal ladder that leads from the roof down inside the structure. It’s much darker inside with no outside door and a long thin window for viewing.
You also get some better views of the long stretch of coastline going south, which includes Ulehawa Beach Park, Nanakui Beach, the Hawaiian Electric Kahe Power Plant (known for good snorkeling in front), the Ko’olina Lagoons & hotels, and all the way to Barbers Point.
You might notice the trail continues beyond the 4th pillbox, but there is not much to see beyond this point. The trail continues to narrow and cuts through the tall wild hillside grass for about 600 feet, before descending back down to the highway. It is much less traveled and we do not recommend hiking this route.
Reviewing some of the directions provided online, it sounds like you'll have to pull over on the side of the highway along a telephone marker to start the hike. I was very happy to discover that this is not the case, unless you want to scale up the side of the steep mountain on a loose-gravel trail.
When you're arriving in the area, keep your eyes peeled and you should see the first pillbox sitting pretty up top. It’s hard to miss as it has been painted the color pink.
From Waikiki it should take you about a 1 hour to drive to the Maili Pillbox Trail, or about a 15 minute drive from Ko'olina.
From Waikiki to Maili:
Consider driving further north to where the road ends at beautiful Yokohama Bay, and Federal nature preserve, Kaena Point. Heading back to town you will pass by Electric Beach that is known for good snorkeling, and Ko'olina Lagoons that features 3 large Oahu Resorts.
Ka’ena Pt – If you reach the end of the road at Yokohama Beach, there is a 4 mile round trip Oahu hiking trails there. Take a two-mile hike out to the tip of the most northwestern point of the island, and explore beautiful Ka’ena Pt Park, trekking through sand dunes and the jagged reefs along the coastline.
You might want to do another hike to Kaena Point, but once you see beautiful Yokohama Bay, you might just opt to stay right here! There’s a good chance you might have the beach to yourself, as it’s the most isolated beach on the island. There is a lifeguard on duty, but note that it can be rough when waves are present.
Ko'olina Lagoons are the most recently developed area on Oahu where you can find big resorts like The Marriott, Disney's Aulani Resort, and the Four Seasons Resort.
Four man-made crescent-shaped beach lagoons were created for visitors. You do not need to be a hotel guest in order to enjoy these beaches and use the beach facilities, so make a stop and enjoy!
Just 5 miles back down the road towards town is Kahe Beach...better known as Electric Beach.
There are energy-producing towers in the area, and they pump ocean water in and out to help cool the plant. By doing so, it has created a fish frenzy in the water.
Note that you should be an experienced snorkeler and swimmer, as there is a strong rip current in these waters.