Haleigh HendricksonThanks to their short distances, panoramic views, and level of accessibility, the pillbox hikes on O’ahu are popular among both locals and visitors.
There are four main pillbox hikes on O’ahu: Lanikai Pillbox, Maili Pillbox, Ehukai Pillbox, and Pu’u Ma’eli’eli Pillbox. These trails are not as adventurous as more challenging routes such as Moanalua Valley Trail or Ka’au Crater Trail, but they lead to incredible views, making them a popular trail option on O’ahu.
If you’re short on time, not looking to spend all day hiking, or in search of amazing views that don’t require a huge amount of effort, the pillbox hikes are for you.
In this guide, I cover the four pillbox hikes on O’ahu, as well as highlight which trail is the easiest, hardest, and most popular. I also include other trails around the island where you can find additional pillboxes to explore.
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Complete Guide to the Pillbox Hikes on O’ahu
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Commonly Asked Questions
Why Are They Called Pillbox Hikes?
On several trails around O’ahu, hikers can spot old concrete structures referred to as “pillboxes.” The United States Military built these pillboxes and used them for purposes of defense or observation.
Though the military no longer uses these structures, many of them remain intact and are accessible via a variety of trails around O’ahu.
Which Pillbox Hike Is the Best?
I’m not sure there is an overall consensus on which pillbox hike on O’ahu is the best. My favorite pillbox hike is Maili or “Pink” Pillbox, although I’m sure others would disagree.
With that being said, it is undisputed that the most popular pillbox hike on O’ahu is the Lanikai Pillbox hike. People flock to the Lanikai Pillbox for the chance to see the crystal blue water backdrop of the Mokulua Islands.
Which Pillbox Hike Is the Hardest?
All four of the main pillbox hikes on O’ahu are around 1.5-2 miles, and gain around 600-700 feet of elevation. While each pillbox hike is similar in stats, some trails are more exposed than others.
I would argue it’s a toss-up between Lanikai Pillbox and Maili Pillbox, for the simple fact that both trails have almost zero coverage from the sun. However, if you can complete one pillbox hike you can complete them all.
If you have a goal to hike all of the pillbox trails on O’ahu, go for it.
Which Pillbox Hike Is the Easiest?
Each of the four pillbox hikes on O’ahu is of similar difficulty and distance. Though the trails are steep, each trail is generally considered a doable route for most people.
If I had to choose, I would say that Pu’u Ma’eli’eli Trail is the easiest pillbox hike on O’ahu. Pu’u Ma’eli’eli Pillbox covers the least amount of elevation and is the least exposed to the sun. The majority of the trail occurs under thick tree canopy, unlike the other pillbox hikes on O’ahu.
Keep in mind that even hikes rated “easy” on O’ahu still require a substantial of stamina, scrambling, and balance. At the end of the day, these pillbox hikes are still hikes, not walks, and should be treated as so.
The 4 Best Pillbox Hikes on O’ahu
The pillbox hikes on O’ahu are a great option for people visiting the island looking to score some incredible views without having to be an experienced hiker.
Many of the island’s best views are on challenging trails such as Olomana Trail or Kuli’ou’ou Ridge and are only appropriate for seasoned hikers in peak physical shape. However, The pillbox hikes on O’ahu are accessible to hikers of all ages and experience levels making them a bucket list adventure for many visitors and locals alike.
For stunning views that won’t take all day to reach or leave you feeling exhausted, explore these four pillbox hikes on your next trip to O’ahu.
Lanikai Pillbox
The Lanikai Pillbox hike is the most iconic and popular pillbox hike on O’ahu. At the top, hikers can get an unobstructed view of the Pacific Ocean and the nearby offshore Mokulua Islands.
As with all pillbox hikes on O’ahu, the trail is short and sweet, albeit steep. Lanikai Pillbox Trail wastes no time in putting hikers to work as the trail makes its way uphill with no switchbacks.
The trail is hot and exposed and should be treated as a hike, despite its short 1.7-mile length. Because the trail offers no shade, the best time to enjoy the Lanikai Pillbox hike is at sunrise. You can escape the heat and score front-row seats to the sun making its debut over the ocean.
Allow enough time to return to your car before nightfall if you are hiking the trail for sunset. Pack a headlamp, just in case.
There are two pillboxes along the trail and both award great views of Lanikai Beach, the Mokulua Islands, and the Ko’olau Mountain Range.
Maili Pillbox
Maili Pillbox, though not as popular as the Lanikai Pillbox, is my favorite pillbox hike on O’ahu. Unlike some of the other pillbox hikes around the island, this trail doesn’t just have the best for last. Maili Pillbox, commonly referred to as Pink Pillbox is located on the underrated west side.
While its distance is short at just over 1.5 miles, the trail is steep with obstacles of rocks, tree roots, loose scree, and dirt. Despite its short length, the trail unsurprisingly over-delivers on views. For most of the trail, hikers get unobstructed views of the west shore and Wainanai Mountain Range.
Once you do reach the top you’ll find a couple of pillboxes to explore, including the iconic pink pillbox.
Sunset is the most enjoyable and stunning time of day to hike the Maili Pillbox Trail. Completing it at sunset helps you beat the heat while awarding you a picturesque sunset over the ocean.
If you’re looking for the best place to watch the sunset on O’ahu, this trail is it. Keep in mind, you’ll be sharing the experience with several other eager-sunset goers. If you can get yourself to Maili Pillbox on a weeknight, even better.
Ehukai Pillbox
Though it doesn’t receive near the hype as Lanikai Pillbox or Pink Pillbox, the Ehukai Pillbox hike is, hands down, the best hike on O’ahu’s north shore.
Though most visitors visit the north shore for its laid-back vibe, stunning beaches, and world-class surf breaks, that doesn’t mean hikers are out of luck.
Ehukai Pillbox Trail is an easy-moderate route and takes around 1-2 hours to complete. The trail is short, sweet, and steep and is generally considered an accessible route for hikers of all ages and experience levels.
Even though you only gain about 700 feet of elevation, the view from the top of the trail is stunning and worth the scrambly quad burner it takes to get there.
Like the other pillbox hikes on O’ahu, expect to share the view with many other hikers. Early mornings and weekdays are the best time to explore the Ehukai pillbox hike if you’re hoping to avoid the crowds.
There are two pillboxes on the Ehukai Pillbox hike and both award hikers with stunning views of the north shore coastline. If you can time it correctly, sunset is the most magical time of day to complete this trail as you’ll get front-row seats to watch the sun dip below the horizon.
If you happen to be on the trail during the winter months (November-March), keep your eyes open for whales and enjoy the surfers surfing the iconic Pipeline.
Pu’u Ma’eli’eli Pillbox
Pu’u Ma’eli’eli Pillbox, also referred to as the Kaneohe Pillbox, is perhaps the least talked and least popular about pillbox hike on O’ahu. The good news is, that means it’s usually less crowded than the others.
Pu’u Ma’eli’eli Pillbox is a short and easy trail located on the east side of O’ahu near Kaneohe. With only 600 feet of elevation gain, most of the trail is relatively flat and manageable but it does have sections of steep elevation. Expect roots and rocks and one manageable rope section.
With its location on the east side, the most magical time of day to hike Pu’u Ma’eli’eli Pillbox is in the morning. Keep in mind that there is only one pillbox and viewpoint on Pu’u Ma’eli’eli Trail. Expect a crowded viewpoint if you complete the hike on the weekend or during peak times.
As with the other pillbox hikes on O’ahu, the trail only takes about 1-2 hours to complete. Though most of the trail is surrounded by trees, the lookout at the end makes the uphill trek worth it.
From the pillbox, hikers get to witness sweeping views of Kaneohe Bay, the Kaneohe sandbar, Coconut Island, Kualoa Ranch, and more.
Additional “Pillbox” Hikes on O’ahu
While the Lanikai Pillbox, Maili Pillbox, Ehukai Pillbox, and Kaneohe Pillbox are the four trails most commonly referred to as the “pillbox hikes on O’ahu,” they are not the only trails with pillboxes.
You can find pillboxes scattered about the island and spotted on many popular trails, including these favorites below.
Diamond Head Summit Trail
Diamond Head is perhaps the most recognizable landmark in Hawai’i and deserves a visit on any trip to O’ahu. The trail takes hikers to the top of Diamond Head where you can enjoy panoramic views of the volcanic crater, Waikiki, the expansive coastline, and the Ko’olau Mountains.
Diamond Head Summit Trail is just under 2 miles and involves sections of pavement, dirt, and metal stairs. The trail is relatively easy but does involve a steady incline.
Expect the trail to be hot and crowded, regardless of what time you go. Reservations to hike Diamond Head Summit Trail must now be made in advance. Entry is $5 and Parking is $10.
Makapu’u Point Lighthouse Trail
Makapu’u Point Lighthouse Trail is a beautiful hike located on the eastern coast of the island near Waimanalo. Roughly 2 miles road trip, the trail is paved and well maintained making it a great option for those looking to experience beautiful views without getting down and dirty.
While the trail’s main attraction is the lighthouse, the trail also houses another pillbox. This pillbox is less frequented than the others on this list as it is not the highlight nor part of the main trail.
Makapu’u Point Lighthouse Trail is open from dawn to dusk and busy at nearly all times. Although the trail is paved, the route is steep and exposed so make sure to come prepared.
Koko Crater Trail
The Koko Crater Tramway Trail, commonly referred to as “Koko Head,” is undoubtedly one of the most popular hikes on O’ahu. It is equally frequented by locals and visitors and heavily trafficked year-round. Consisting of approximately 1,000 stairs, Koko Crater Tramway Trail is less of a hike and more of a workout.
Although the trail is extremely popular it should not be underestimated. Completing Koko Crater Trail is extremely challenging, physically taxing, and mentally trying. Those who are able to make it to the top are rewarded with 360° views.
While the stair challenge is what draws people to the trail, hikers can also explore the old pillbox at the top.
Make sure to check out my other O’ahu guides to help plan your trip or fill your weekend with adventure. If you have any questions about the Pillbox hikes or other trails around the island, leave me a comment in the section below.
Happy adventuring!
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