Distance: Depends on which route you take, but can take one-hour round trip
When to go: Early to mid-morning as there is not much shade, so you are exposed to the sun or at sunset because West O`ahu has spectacular sunsets
I’ve lived in West O`ahu for nearly two years and cannot believe I’ve never done the Maili Pillbox Hike before. Only 15 minutes from my door, the drive here was super easy. Head straight down Farrington Hwy and pass through Nanakuli. When you arrive at Kaukama street, turn right. As soon as you turn right, begin counting the light poles because the trail begins at the 9th light pole on the right. Street parking is a cinch compared to other O`ahu hikes. A large shoulder on both sides of the road allow for ample parking.
The trail begins by merely stepping off the sidewalk and onto the rocky trail. We had been told that the first 10 minutes of the hike would be the most difficult, but didn’t believe it. How could that be when the pillbox we were trying to reach was soaring above us? It turned out, however, to be true.
After about 15 minutes, we came to this tree with exposed roots that looked straight out of the Lion King. Venturing on a little further, we came to a second identical tree growing out of the rocks. This marked the halfway point of the trail. The trail overall was a mix of rocks and smoother dirt, flanked on both sides by tall grasses and brush.
After passing the second Lion King tree, we came to a literal fork in the road. We had been advised by a fellow hiker earlier in the trail that if we took a left it would essentially mean that we would be scaling the rocky cliffs on the more direct route to the top. If we went right, we would basically zig zag up the face of the mountain, making for a longer but easier trail. Without question we took a right, heading the fellow hiker's warning of not wanting to “see you on the news that night.”
We wound our way up to the top and were immediately treated with spectacular views before even getting to the top. When we reached the first pillbox, the view got even better. I didn’t want to be deterred though. I came here for one thing: the pink pillbox. Climbing on a little further, we reached the pink pillbox and the view was even better. Plan to spend some time up there taking photo after photo.
You have the option to continue on to the farthest pillbox, however this meant walking along a narrower ridge of rocks and honestly, I was content enough with the three other structures we took photos at.
We lucked out with the weather being beautiful. Some clouds gave us relief from the sun and the cool breeze made it downright pleasant. All of this, however, did not stop us from getting some pretty gnarly tan lines due to direct sun exposure 90% of the time.
The route down went, of course, much faster than going up, however it’s a little more challenging with having to dodge all of the rocks and get your steady footing.
Overall, this has been one of my favorite hikes because of the great trail, the ease of the hike, and the rewarding views. Should you find yourself on the west side, consider making the trek up. You’ll be rewarded handsomely.