Hiking the Kaipapaʻu Pillbox Trail on the North Shore of Oʻahu, Hawaiʻi
Distance: 2.7 miles / 4.3 km
The Kaipapaʻu Pillbox Trail, also known as the Kaipapaʻu Bunker Trail, is a relatively short out-and-back hike on the North Shore of Oʻahu to one of the island’s most hidden WWII-era bunkers, and because it’s so unknown, the Kaipapaʻu Pillbox is one of my personal favorite sunrise hikes on the island!
It’s for exactly this reason that I choose to keep this information off some of my related island posts—such as my 'Best Things to Do on Oʻahu' and 'Best Oʻahu Sunrise Hikes' articles—so that this local trail doesn’t become more popular than it ever should.
This aside, the Kaipapaʻu Pillbox is fairly out of the way for most hikers looking for a fun sunrise adventure, as most people from town or the east side don’t drive further north than Crouching Lion, making the Kaipapaʻu Pillbox Trail one of the least-crowded places on Oʻahu to catch the sunrise!
Kaipapaʻu Pillbox Trailhead Parking
Parking for the Kaipapaʻu Pillbox Trail is located at the very end of Kawaipuna Street in Hauʻula on the North Shore.
That said, please park legally and do not block someone’s driveway.
Additionally, it will likely be difficult to remain completely quiet, as there are so many dogs in the neighborhood, but still, I kindly ask that you do whatever you can to not draw negative attention to this trailhead. Local hikes need to remain local.
Google Maps Directions: Kaipapaʻu Pillbox Trailhead
My Hawaiʻi Hiking Checklist
Osprey 3L Water Bladder - The Osprey 3L water bladder is the most universal hiking and backpacking water bladder on the market, and it’s my go-to because of the slide-off seal that allows it to be quickly filled from the top. Additionally, individual parts are easily replaceable, such as the bite valve.
Blister / Heel Protectors - I swear by these cheap, amazing heel protectors to prevent blisters for nearly every kind of hiking and backpacking that I do!
Black Diamond Headlamp - Personally, I recommend the Black Diamond Storm because it is one of the brightest, lightest, and longest-lasting headlamps on the market—and trust me, the weight-to-battery-life ratio really does matter!
Hiking / Trail Running Shoes - Depending on the type of trail, I prefer to use either the Keen Targhee for longer, more rugged hiking or the HOKA Zinal Trail-Running Shoe for lighter, less intense trails. In either case, both have been amazing to me for many years across countless environments, and both can be found in men’s and women’s sizes. - (Men’s Keen / Women’s Keen) (Men’s HOKA / Women’s HOKA)
Waterproof Rain Shell - You never know when it may rain, and I’ve learned over the years that a rain shell is far better than a rain jacket. By this, I mean that it’s best to have something that the water will roll right off of, which is why I recommend the Patagonia Torrentshell 3L available in both men’s and women’s sizes.
High SPF Sunscreen - Packing high-SPF sunscreen is a must for long days outside!
Hiking the Kaipapaʻu Pillbox Trail
Initially, the Kaipapaʻu Pillbox Trail begins up this service road at the end of Kawaipuna Street before branching off on the real trail just behind the water tank.
As previously mentioned, please do what you can to be respectful in this Hauʻula neighborhood, especially because the Kaipapaʻu Trailhead is used for both the pillbox and the Kaipapaʻu Gulch Trail.
It’s here, just past the water tank, where both the gulch and Kaipapaʻu Pillbox Trail continue.
Kaipapaʻu Pillbox-Kaipapaʻu Gulch Junction
At the first clearing after the water tank, make a hard right turn up the hill to continue on the Kaipapaʻu Pillbox Trail.
The trail that continues straight is what leads deeper into Kaipapaʻu Gulch.
After the split, the Kaipapaʻu Pillbox Trail begins climbing steeply between 400-500 ft. of elevation until the top of the ridge, where the trail levels out.
There was lots of Noni when I hiked on this day, but if you don’t know, Noni is edible; however, it’s not a fruit that you want to eat.
If you notice this split in the trail, stay to the left to continue toward the pillboxes.
Almost immediately after the split, the trail will dip down into this small ravine, which is a good sign that you went the correct direction.
When the trail comes to this open erosion scar on the ridge, you can either scramble up the ridge to continue further or take the easier route and go left, which is a bit more gradual in order to get up the hill.
Kōloa Gulch-Kaipapaʻu Pillbox Junction
Had you gone left, the trail splits here, with the Kaipapaʻu Pillbox Trail continuing on the ridge to the right, as well as the loop that leads around to Kōloa Gulch.
Personally speaking, I think that it’s kind of excessive to start at the Kaipapaʻu Trailhead if your intentions were to hike Kōloa Gulch. That's why, if you’re interested, I encourage you to check out my separate Kōloa post, which has a much more direct trailhead as opposed to Kaipapaʻu.
Read My Separate Post: Kōloa Gulch Trail
After the Kōloa junction, the Kaipapaʻu Pillbox Trail levels out significantly compared to the beginning of the hike, even descending a bit to reach the two bunkers at the end.
Toward the end of the Kaipapaʻu hike, the trail will pass by the first of two bunkers, with the best one being the last, overlooking the North Shore, as shown below.
Kaipapaʻu Pillbox
From the Kaipapaʻu Pillbox, you get great views of Lāʻie and Kahuku to the north, as well as Hauʻula down to Punaluʻu to the south.
All said, making the Kaipapaʻu Pillbox a sunrise hike is more involved than most on the island, especially since it’s a little longer than comparable sunrise hikes. However, I think this is what makes Kaipapaʻu my favorite because you’re almost always guaranteed to have it to yourself. Therefore, I kindly ask that you please keep this one a secret and off social media.
To that point, posts such as this do not and never will have the same impact at exposing a place as social media does. Therefore, I wanted to create this article for the purpose of providing an accurate description of the trail, not to make a local hike more popular.
Native Plants on the Kaipapaʻu Pillbox Trail
The Kaipapaʻu Pillbox Trail is a very low-elevation Hawaiʻi hike, meaning that the vast majority of the plants you will see are non-native/ invasive species.
Nevertheless, there are a few natives that you can find on the trail, with one of the most dominant being ʻŪlei. In addition, you can expect to see ʻĀkia, ʻUhaloa, Kaunaʻoa, and if you’re lucky, you might spot an ʻŌhiʻa tree or two.
All said, if you would like to learn more about these and other native Hawaiian plants from across the islands, I encourage you to scroll through my separate post.
Read My Separate Post: Native Hawaiian Plant Guide
More Oʻahu Adventures
If you’re interested in reading about some more amazing Oʻahu adventures, check out my separate posts below!
Best Hotels & Restaurants in Waikīkī
If you’re trying to decided where to stay on Oʻahu, check out my top 10 list for the best resorts and restaurants in Waikīkī.
I break down what makes one hotel a better choice over another, so that you can find the best fit for your stay on the island.
Read My Separate Post: Best Waikīkī Hotels & Restaurants
Waikīkī
HNL Airport-Hotel Shuttle
Prices on ride-share apps like Uber/ Lyft cannot beat the price of booking your hotel shuttle prior to arrival. I say this because there are additional fees for ride-share airport pick-ups at Honolulu Airport (HNL), which is why I recommend booking your transportation in advance using the options below.
Additionally, the last option below will go as far as the Ko ʻOlina Resorts on the West Side and Turtle Bay on Oʻahu’s North Shore!
Best Way to Book Rental Cars!
I travel quite a bit, and I know firsthand that finding a good rental car deal can be a challenge, but that’s why I recommend comparing all of your options with Discover Cars.
In short, Discover Cars is a well-known, reputable business that allows you to search for the best deal across companies, and they have the best full-refund cancellation policy I’ve ever seen, valid up to 72, or sometimes even 48, hours prior to your reservation!
Book Here: Discover Cars
Oʻahu
Visiting Other Islands
If you are visiting Oʻahu or heading to another island, check out some of my personal recommendations for Oʻahu, Maui, Kauaʻi, Molokai, Lānaʻi, and Hawaiʻi Island (Big Island) in these separate posts.
If you’re trying to decide which island is right for your visit, check out my overview about each island in the post below.
Read My Separate Post: What is the Best Hawaiian Island to Visit?
What is the Best Time of Year to Visit Hawaiʻi?
The weather in Hawaiʻi can often appear to be warm and beautiful throughout the year, but in my experience, there is a lot more to consider when planning what time of year to visit the islands, such as what island you are considering, what sides of each island do you plan to stay, what activities are you most interested in, the wildlife, and countless other nuanced variables that can all impact the type of trip you can expect to have.
For these reasons, I highly recommend reading through my separate article to not only understand my thoughts regarding the best time of year to come to Hawaiʻi but also what you need to consider based on the time of year that you plan to visit.
Read My Separate Post: What is the Best Time of Year to Visit Hawaiʻi?
10 Best Tours & Excursions on Oʻahu
There are a lot of different tour options to choose from on Oʻahu, but to make it easier to decide, I made a list of my favorite tours because some things simply are better with a local guide!
Read My Separate Post: Best Tours on Oʻahu
Oʻahu
Safety
All hikes in Hawaiʻi should not be compared to trails outside of the islands, and hikers should exercise due caution on every adventure, given that many are extremely dangerous.
By this, I mean that Hawaiʻi is known for hot, humid weather, steep, dramatic, and unstable cliffs, and flash floods, which can occur without warning. Therefore, it is important that you check the local forecast, understand the physical condition of your entire group, and pack sufficient food and water before attempting any adventure.
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