Hiking the ʻAikahi Pillbox (Kalāheo Hills) Trail on Oʻahu
Distance: 1.6 - 2.8 miles / 2.6 - 4.5 km
The distance above is variable because you can start or end at a few different trailheads to reach the ʻAikahi Pillbox. In this post, I started at the most popular ʻIli ʻĀina Trailhead and ended at the ʻIlimano Trailhead.
Most importantly, the AllTrails GPS track starts at ʻIli ʻĀina but does not take you all the way to the pillbox. However, for the sake of a sunrise hike, the hill that the GPS stops at is a good destination.
Overall, the ʻAikahi Pillbox Trail makes for a great uncrowded sunrise hike compared to the neighboring Lanikai Pillboxes.
Note that the Kalāheo Hills is a NOT a public hiking area, and you accept all potential legal consequences for entering a closed area.
ʻAikahi Pillbox Trailhead Parking
Parking for the ʻAikahi Pillbox hike is residential parking near 643 ʻIli ʻĀina Street in Kailua. This is the most popular Kalāheo Hills Trailhead.
If you’re going to hike ʻAikahi for sunrise, be quiet in this residential neighborhood. This is truly a locals only hike, and there’s no need to draw negative attention to this area.
Google Maps Directions: ʻAikahi Pillbox Trailhead
Hiking the ʻAikahi Pillbox Trail
Don’t forget to pack a headlamp for a sunrise hike.
The ʻAikahi Pillbox hike starts at the same trailhead as the Kalāheo Hills BMX track. Being the case, you need to be paying attention when you go around blind turns or you risk serious injury from a collision.
Generally speaking, most directions head up, but if you follow the turns in this post, you’ll take the most straightforward route to the top.
At this first split, go left. The second photo is the same turn from a different angle.
It’s easiest to hike around these little jumps.
At the second split, you can go either direction. I went right, but the left split may be slightly faster to reach the same place.
At this junction, go left up the hill. This is almost the top of the ridge line.
At this split, go right. The ridge line will be shortly after. Turn right when you meet it to head up to the lookout.
This small summit is where the AllTrails GPS ends, and it’s also the most popular stopping point on the Kalāheo Hills hike.
However, to reach the ʻAikahi Pillbox, you need to continue toward the towers.
The ʻAikahi Pillbox
To reach the pillbox, continue hiking along the ridge on the most obvious trail. The trail gets steep and loose in a few sections because the ridge heads down and up a few hills with loose rocks after the main lookout.
Go left at this small junction. This small split might not look like much, but it is the way to go for an alternate route up and down from 601 ʻIlimano Street.
Once at the towers, head down the stairs and up the road.
There will be a small gap at the top of the hill on the right side to follow a trail around the fences and out to the pillbox.
Hiking Down ʻAikahi
On my way back, I took the left split to head down to ʻIlimano Street because it’s faster. By comparison, it’s only 0.4 miles (0.6 km) to reach this spot from ʻIlimano Street compared to 0.9 miles (1.4 km) from ʻIli ʻĀina Street.
It can be a good way to head up if you don’t care about the first lookout, but it’s slightly more overgrown so it depends on what you prefer.
Go Left for ʻIlimano Street / Go Right for ʻIli ʻĀina Street
Heading Down to ʻIlimano Street
Heading Down to ʻIlimano Street
Heading Down to ʻIlimano Street
Heading Down to ʻIlimano Street
Almost There!
Turn left here to head out to the street.
Go Left
From the ʻIlimano Street Trailhead it was a quarter mile walk back to the ʻIli ʻĀina Trailhead. This road walk back is much nicer and faster than hiking the ridge back.
ʻIlimano Street Trailhead
Pau!
The ʻAikahi Pillbox - ʻIli hau Route
Distance: 0.5 miles / 0.8 km
Compared to the first two trailheads above, the ʻIli hau Street Trailhead is my least favorite route to reach the ʻAikahi Pillbox which is why I included it last here.
Overall, the ʻIli hau route is a bit more overgrown than the other two, and the first part of the hike brings you through someones backyard. For these two reasons I’d say stay clear of this route, but incase your curious to see what it’s like, I thought I’d include it.
ʻAikahi Pillbox - ʻIli hau Route Parking
Finding a good parking spot on ʻIli hau Street is not as easy as other residential streets. I recommend turning off on one of the side streets to find parking instead of driving all the way up to the trailhead.
Google Maps Directions: ʻAikahi Pillbox Trailhead
Hiking the ʻAikahi Pillbox - ʻIli hau Route
The ʻAikahi ʻIli hau route starts at the very end of ʻIli hau Street.
The trail continues on the far side of this yard, and I ask that you be quiet and respectful if you are going this way.
At the top of the little hill in the photo above, there’s a small drainage where you will need to turn left to continue on the correct trail.
Once you reach the water tank, you can either go through the fence here or continue on the outside like I did in the photos below.
Duck through the fence here.
Side Trail (ʻAikahi Lower Pillbox)
At this less obvious split in the trail, you can go right to check out a little lesser known pillbox or left to continue to the ʻAikahi Pillbox.
Back on the ʻIli hau Route
I believe the most annoying part of the overgrowth is after the split on the left to continue heading up to ʻAikahi. This part through the tall grasses will continue for a little while before popping out on the ridge that leads up to the pillbox.
The rest of the ʻAikahi Trail from this point on is very self-explanatory.
Native Plants on the Kalāheo Hills
Since the ʻAikahi Pillbox hike is entirely a low-elevation trail for Hawaiʻi, native Hawaiian plants are few and far between. The only one that stood out to me was ʻUhaloa.
If you’d like to learn more about identifying native plants around Hawaiʻi, check out my separate post that I wrote specifically to help others learn more about our native plants across these beautiful islands.
Read My Separate Post: Native Hawaiian Plant Guide
