Hiking the Kahekili Ridge Trail & Pillbox on Oʻahu
Distance: 0.8 miles / 1.3 km
The Kahekili Ridge Trail on the east side of Oʻahu is one of the island’s least-visited trails.
For this reason, the short 0.4-mile (0.6 km) trail to the pillbox above Kaʻaʻawa makes for one of the best uncrowded sunrise hikes, especially when compared to the neighboring Crouching Lion Trail.
However, this is all without saying that Kahekili Ridge, along with Crouching Lion, are really just the footsteps of the much longer trail to connect the two of them together, known as Puʻu Manamana. To learn more about this day hike, I highly recommend reading my longer summary at the end.
Kahekili Pillbox Trailhead Parking
Parking for the Kahekili Ridge Trail is located at either Swanzy Beach Park or on Huamalani Street, where the trailhead is located.
Personally, I typically park at Swanzy Beach Park to try and help keep this local trail quiet, as negative attention—meaning noise and trash from hikers—does not need to be brought upon this small neighborhood.
Google Maps Directions: Huamalani Street / Swanzy Beach Park
Hiking the Kahekili Ridge Trail
The Kahekili Ridge Trail begins at the very end of Huamalani Street at the unmarked trailhead shown below.
This is also the trailhead for Makaua Falls.
Kahekili Ridge-Makaua Falls Junction
Initially, the beginning of the Kahekili Ridge Trail will be flat until the trail comes to this junction shown below.
Here, both the Kahekili Ridge and Makaua Falls Trail split, which is where you want to go left to begin climbing up Kahekili Ridge.
After the split, the trail will begin the steep 400-ft. (122 m) climb up to the ridge crest, where the pillbox is located.
From this sharp switchback on the ridge, the pillbox is less than 0.1 miles (0.2 km) away.
Kahekili Pillbox
In my opinion, the best views—especially for sunrise—are not at the pillbox but above, where the overgrowth clears, and the views to the east really open up!
What is the Puʻu Manamana Loop Trail?
Distance: 5.3 miles / 8.5 km
In short, the Kahekili Ridge/ Pillbox Trail is really only the footstep for the much longer Puʻu Manamana-Kahekili Ridge Loop Trail.
What this means is that the longer 5.3-mile (8.5 km) loop can either begin here on the Kahekili Ridge Trail or on the Crouching Lion side, located near Kahana Bay Beach Park.
That being said, don’t let the moderately short 5.3-mile distance influence your perception about how hard the trail is, as Puʻu Manamana is not a beginner hike.
By this, I mean that if you were only prepared to hike to the Kahekili Pillbox, don’t proceed up the ridge. You are not prepared for the longer Puʻu Manamana Loop. Additionally, Puʻu Manamana features numerous high-exposure class 3/ class 4 climbs, where a mistake is simply not an option.
If you would like to learn more about the full Puʻu Manamana-Kahekili Ridge Loop, I encourage you to read about the full trail using the link below.
However, if you had any difficulty on the Kahekili Ridge Trail up to this point, then you should not hike Puʻu Manamana. It’s steeper, more exposed, the consequences of falling are much greater, and there are sections that require climbing, which typically means climbing wet/ slippery rock. I say all this to inform you the best I can.
Read My Separate Post: Puʻu Manamana-Kahekili Ridge Loop Trail
Native Plants on the Kahekili Pillbox Trail
For the most part, the Kahekili Ridge Trail is a heavily-invaded trail, with very few native plants until you make it high above the pillbox.
However, there are a few native plants on the lower portions of the Kahekili Ridge Trail, which are ʻUhaloa, Hau, ʻŌhiʻa lehua, and ʻIlima, to name a few.
If you would like to know more about these and tons of other native Hawaiian plants from across the islands, I encourage you to check out my separate post linked below.
Read My Separate Post: Native Hawaiian Plant Guide
