Hiking the Ka’iwa Ridge Trail and Lanikai Pillboxes in Oahu

 

Hiking the Ka'iwa Ridge Trail and Lanikai Pillboxes in Oahu

On Friday February 9th 2018 my friend Lauren and I hiked the Ka’iwa Ridge Trail in Kailua Oahu, Hawaii.

This trail has become very popular with tourists because of how easy it is to get from the trailhead to the abandoned military pillboxes at the top. This popularity makes the well-known section of this trail quite crowded; but you can avoid that if you replicate our hike! Read on for my advice on how to experience this beautiful trail (mostly) in solitude.

The trailhead for this hike is marked in Google Maps as “Pillbox Hike” but the trail is actually called the Ka’iwa Ridge Trail.

You can find parking in the neighborhood at the base of the mountain; just be polite and don’t park on private property, don’t be loud and annoying to residents, and don’t litter. Finding a spot will be difficult on weekends; we went on a Friday and had to drive around for 15 minutes before finding a spot.

Pillbox Hike Trailhead
To access the trailhead you’ll want to walk up Kaelepulu Drive to 414 Kaelepulu Drive. Historically Google Maps shows no trailhead here because it was originally located on the side street shown in the above photo.
Pillbox Hike Trailhead
Now, due to overwhelming crowds on this trail, they have moved the trailhead from the side street out directly on to Kaelepulu Drive to the left of the original chain link fence.

Once you find the trailhead, it’s a quick and easy .9 mile hike to the top. On the way up you will pass a TON of tourists who are going up, and back down. For some reason, all of the tourists think that the trail ends at the second pillbox; luckily for the rest of us, the trail continues well past that point.

Right from the beginning, you will have stunning views of Lanikai and the Mokulua Islands State Seabird Sanctuary
Right from the beginning, you will have stunning views of Lanikai and the Mokulua Islands State Seabird Sanctuary
This is the view from the first pillbox.
This is the view from the first pillbox.
Lauren looking out at the Mokulua Islands State Seabird Sanctuary
I took this photo to show you how steep the mountains are...it's pretty impressive, and breathtakingly beautiful!
I took this photo to show you how steep the mountains are…it’s pretty impressive, and breathtakingly beautiful!
The main part of the trail up to the 2 pillboxes is very well worn, but very fun to jog up!
The main part of the trail up to the 2 pillboxes is very well worn, but very fun to jog up!
Lauren & I jogged a lot of the Lanikai Pillbox trail; it's pretty popular with trail runners.
Lauren & I jogged a lot of the Lanikai Pillbox trail; it’s pretty popular with trail runners.
You can see why the Lanikai Pillbox hike has become so popular.
You can see why the Lanikai Pillbox hike has become so popular.

Once you reach the second pillbox, at the top of the mountain, you’ll likely be amongst a dozen or more other hikers. This is the point that you’ll want to continue on. There are quite a few different trail options from this point forward, the one we decided to do (without having a map or knowing where we would end up!) wound up being 3 miles.

This is the view looking back down the trail from the second pillbox, with the first pillbox visible in the distance.
This is the view looking back down the trail from the second pillbox, with the first pillbox visible in the distance.
I couldn’t believe how steep the Eastern side of these mountains were!
This map shows you the standard "Pillbox Hike" out-and-back trail as a blue dotted line. Lauren & I continued on along the Ka'aiwa Ridge which I've shown as a green line on the above map.
This map shows you the standard “Pillbox Hike” out-and-back trail as a blue dotted line. Lauren & I continued on along the Ka’aiwa Ridge which I’ve shown as a green line on the above map.

The map above shows you the out-and-back Pillbox Hike in blue. The Green line is what you’ll want to follow from the summit if you want to have a beautiful hike alone without any company on the trail. This portion of the trail is absolutely stunning, and is slightly overgrown, giving it a magical feeling. The purple line shows another option that we haven’t tried yet, but will likely attempt soon.

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We only saw two other people on the last 2 miles of the hike, so it was a great decision to continue on past the summit.

After about a mile (I didn’t measure) you will come to an intersection where the trail continues straight west and goes down to Kamahele Street. Take the side spur that leads way out to the East.

You'll see this amazing ridge that points straight East once you reach the split in the trail. Take the spur to your left to access this leg of the hike. You'll be going all the way up to the summit of that mountain.
You’ll see this amazing ridge that points straight East once you reach the split in the trail. Take the spur to your left to access this leg of the hike. You’ll be going all the way up to the summit of that mountain.

We saw this ridge (above) that goes directly East towards the ocean at the southern end of Lanikai Beach…but we had no idea if we’d be able to find a way down to the neighborhood from that point. We decided to give it a shot anyway; we were lucky and found an exit trail that brought us down to Luika Place so we didn’t have to go all the way back to the summit, and then back to the trail head. We jut couldn’t resist seeing where the trail would lead us.

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You'll see this amazing ridge that points straight East once you reach the split in the trail. Take the spur to your left to access this leg of the hike. You'll be going all the way up to the summit of that mountain.
You’ll see this amazing ridge that points straight East once you reach the split in the trail. Take the spur to your left to access this leg of the hike. You’ll be going all the way up to the summit of that mountain.

After about 2.9 miles from the trailhead, you’ll reach the summit above the south end of Lanikai Beach. From here we took a wild guess that the rain wash on the side of the mountain would lead us down into the neighborhood, and back to our car. As you can see int he above map image, you could also probably continue along the purple line that I highlighted, and then descend down to Lanikai as well.

This shot from the final summit that we reached gives you a great view of the Pillbox Hike. The trailhead is in the far distance and goes up that ridge to the highest point on the left. You might be able to make out the 2 pillboxes way off in the distance on top of the ridge.
How adorable is Lauren??
We were super stoked that we found a way back down to Lanikai from this point; saved us a trip all the way back up to the summit, and down to the beginning!
When you find this marker on the ground, take a left here and head about 300 feet straight down the side of the mountain. It’s very steep, but an amazing shortcut!
Once you descend the 300 foot wash trail you will end up at 211 Luika Place, the trail exits right where that orange cone is. From here you can walk through this beautiful neighborhood and see the homes along Lanikai Beach on your way back to your car.

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