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.
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.
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.
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.
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.
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.
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.