Back in World War II, the U.S. military transformed the hills and ridgelines of Oahu into lookout posts with concrete bunkers — aka pillboxes — to guard Hawaii’s coast. Fast-forward to today, and these same pillboxes have become some of the most iconic and scenic hikes on the island. They may not be defending the shoreline anymore, but they’re winning hearts with epic views and cool war-time vibes.
Whether you’re after a chill hike with ocean panoramas or looking to get your legs burning on a steep climb, there’s a pillbox trail for you. Here’s a guide to the top pillbox hikes on Oahu — complete with local favorites, hidden gems, and a side of history.
1. Lanikai / Kailua Pillboxes
Let’s start with the fan favorite: the Lanikai Pillbox hike. If you’re in the Kailua area, this is the one you can’t skip. It’s short, relatively easy, and serves up dreamy views over the turquoise waters of Lanikai Beach.
You’ll reach the first pillbox after just 15–20 minutes of hiking. Trust us, this spot delivers serious photo ops. Breeze in your hair, ocean below — it’s like Oahu is giving you a hug.
A second pillbox is just 10 minutes farther, and it’s bigger, with graffiti-covered walls and even some hidden interior rooms you can explore. Pro tip: small kids might find the entrance ladder tricky, so the front window is a safer bet.
🥾 Distance: 1 mile (1.6 km) roundtrip
⛰ Elevation Gain: 450 feet (140 m)
💪 Difficulty: Easy
2. Maili / Pink Pillbox
If cotton candy-colored concrete sounds like your vibe, head west to the Pink Pillbox in Maili. This ridge hike overlooks the coastline stretching out toward Waianae, and it’s dotted with several bunkers you can climb on top of or wander through.
It’s not too difficult, though the trail is exposed and can get toasty under the midday sun. Less crowded than Lanikai, this one is perfect for sunset lovers — or lucky hikers hoping to spot whales breaching in the distance.
🥾 Distance: 1.2 miles (2 km) roundtrip
⛰ Elevation Gain: 500 feet (150 m)
💪 Difficulty: Easy / Moderate
3. Ehukai Pillboxes
Nicknamed the “peace pillbox” trail, this one winds through shaded forest trails on the North Shore. You’ll pass two pillboxes — the first one peeks through the trees, and the second rewards you with an open view over Ehukai Beach and the coast.
It starts near Sunset Beach Elementary School, making it a fun, accessible adventure for families.
🥾 Distance: 1.5 miles (2.4 km) roundtrip
⛰ Elevation Gain: 650 feet (200 m)
💪 Difficulty: Easy
4. Diamond Head
An Oahu classic! Hiking up this volcanic crater is a must-do for first-time visitors. The trail is paved and manageable, with railings for safety and wartime bunkers to explore along the way. Once you reach the top, you’ll get sweeping views of Waikiki and Honolulu.
This hike combines Hawaii’s natural beauty with a heavy dose of history — think tunnels, pillboxes, and old military lookout posts.
🥾 Distance: 1.8 miles (2.9 km) roundtrip
⛰ Elevation Gain: 500 feet (150 m)
💪 Difficulty: Easy / Moderate
5. Koko Head
Feeling bold? Koko Head is your test of grit. This hike goes straight up an old railway track, originally built in 1942 to carry supplies to a radar station at the summit. The stairs are steep, relentless, and absolutely rewarding — especially with the panoramic views from the top.
It’s not for the faint of heart, but it’s legendary among locals and fitness junkies alike.
🥾 Distance: 1.6 miles (2.6 km) roundtrip
⛰ Elevation Gain: 900 feet (275 m)
💪 Difficulty: Moderate / Hard
6. Pu’u Ma’eli’eli
Hidden in the greenery of Kaneohe, this underrated trail winds through a lush jungle before popping out at a pair of pillboxes with stunning views of Kaneohe Bay.
It’s peaceful, uncrowded, and just long enough to feel like a mini-adventure. You might even catch U.S. Marine planes taking off and landing at the nearby base.
🥾 Distance: 2.3 miles (3.7 km) roundtrip
⛰ Elevation Gain: 600 feet (180 m)
💪 Difficulty: Easy
7. Ka’ena Point Pillbox
At the rugged western tip of the island lies Ka’ena Point — a wildlife sanctuary and prime sunset-viewing spot. But did you know there’s also a hidden pillbox trail here?
The side path is steep and overgrown, so it’s a bit of a scavenger hunt to find. But once you’re up there, it’s just you, the pillbox, and jaw-dropping views of the ocean and cliffs.
🥾 Distance: 6 miles (9.8 km) roundtrip
⛰ Elevation Gain: 425 feet (130 m)
💪 Difficulty: Moderate
8. Makapu’u Pillboxes
Makapu’u is best known for its lighthouse trail, but if you venture slightly off the path, you’ll discover a handful of hidden pillboxes along the way.
One pops up near the 0.7-mile mark, and four more are tucked into the hillside farther up. Expect great views of the coastline and Koko Crater in the distance — especially if you go at sunrise.
🥾 Distance: 3 miles (4.8 km) roundtrip
⛰ Elevation Gain: 600 feet (180 m)
💪 Difficulty: Easy / Moderate
9. Crouching Lion Pillboxes
This short but steep hike already offers one of Oahu’s most dramatic landscapes — cliffs, jungle, and the sea. But hidden among the trees are a couple of old pillboxes you can clamber on top of for bonus views of Kahana Bay.
It’s not well known, and the pillboxes aren’t marked, but they’re a fun extra on an already epic trail.
🥾 Distance: 0.5 miles (0.8 km) roundtrip
⛰ Elevation Gain: 300 feet (90 m)
💪 Difficulty: Easy / Moderate
10. Turtle Bay Pillbox
This one’s mellow and chill — more of a beach stroll than a hike. Located near Turtle Bay Resort, you’ll reach a weathered pillbox by walking from Kawela Bay. It’s not high up on a mountain, but it’s got its own beachy charm and a shady banyan tree along the way.
Perfect for catching sunset vibes without the leg burn.
🥾 Distance: ~1 mile roundtrip
⛰ Elevation Gain: Minimal
💪 Difficulty: Easy
Bonus WWII Spots
Looking for more military history hikes?
Haiku Stairs (Stairway to Heaven): This legendary (and illegal) climb features 3,922 metal stairs up a mountain ridge, leading to an old Navy radio tower.
Battery Cooper Bunker: Located at Kualoa Ranch, this deep WWII bunker is now part of a Hollywood movie tour featuring Jurassic Park and more.
Final Thoughts
From breezy beach strolls to lung-busting stair climbs, Oahu’s pillbox hikes deliver not just incredible views but a real sense of the island’s wartime past. Whether you're a history buff, a photographer, or just someone who loves a good view, these trails are the perfect way to mix a little adventure with a lot of scenery.
Pack your water, lace up your hiking shoes, and don’t forget the sunscreen — the bunkers are waiting.
