Hiking the Wailupe Loop Trail on Oʻahu
Distance: 5.0 miles / 8.0 km
Located between both Wiliwilinui and Hawaiʻi Loa Ridge, the Wailupe Loop Trail feels like a bit of a hidden gem compared to the surrounding trails that attract many more visitors.
That being said, many other articles regarding the Wailupe Loop Trail talk about the route incorrectly, as they skip the East Middle Ridge altogether, utilizing Wiliwilinui Ridge to the west.
However, the true Wailupe Loop Trail never leaves ʻĀina Haina and follows both the East and West Middle Ridges to create the loop shown below.
Wailupe Loop Trailhead Parking
Parking for the Wailupe Loop Trail is located on Haʻo Street in the very back of ʻĀina Haina.
That being said, please be quiet and respectful in this residential neighborhood, as too many trails in Hawaiʻi draw too much negative attention because people just don’t understand this.
Google Maps Directions: Wailupe Loop Trailhead
Hiking the Wailupe Loop Trail
The Wailupe Loop Trail begins at the very end of Haʻo Street on this unmarked trail through the grass in the photos below.
Then, the Wailupe Loop Trail will follow this path through the bottom of the valley for roughly the next half mile.
Wailupe East-West Middle Ridge Junction
Depending on when you hike, the East Wailupe Middle Ridge junction may or may not have ribbons. I’ve seen both, but it’s been pretty clear to me over the years that someone purposefully removes them from this junction for whatever reason.
That being said, you can continue straight at the East-West junction, but I almost always recommend taking the East Middle Ridge up and the West Middle Ridge down because it makes the ascent much more gradual.
In any case, the East Middle Ridge junction will be located about 0.5-0.6 miles (0.8-1.0 km) from the trailhead, which is important to remember because there are splits off the right-hand side of the trail before East Middle.
East Wailupe Middle Ridge Crossover
Without ribbons, the crossover to the East Ridge may be a little vague, but try to stay on the most obvious path possible, and don’t follow the trails up the streams.
Initially, the crossover will drop down.
When the crossover reaches the first of two stream crossings, don’t follow the trail on the left going upstream.
Rather, go straight/ slightly to the right to continue toward the East Middle Ridge.
This final section before the ridge will likely be the most confusing.
Then, shortly after the first stream crossing will be the second.
While the trail may not look obvious go straight across the stream, and the East Middle Ridge will begin on the left immediately following.
East Wailupe Middle Ridge
After the crossover, you should see a trail on the left.
This is the East Middle Ridge, which will continue for the majority of the ascent until you’re near the summit.
If you notice this split in the trail, go right to stay on the East Middle Ridge, which should start ascending a steep trail shortly after.
On such a steep trail, the views of ʻĀina Haina come quick!
However, after the initial steep climb out of the valley the East Middle Ridge levels off, gaining more gradually than the beginning.
Then, I noticed Kaunaʻoa, an endemic parasitic vine, taking over ʻAkoko, another native Hawaiian endemic.
At two different points on the East Middle Ridge, the trail will contour to the left before regaining the ridge shortly after.
This is the second of the two contours off the left side of the ridge.
Of all the times I’ve hiked Wailupe, the upper elevations are always a bit more overgrown, with the exception of the time I took these photos!
It’s amazing to see the effort some volunteers took to clear the trail, but even at that, their work inevitably can’t keep up with the whole trail, which is why I highly recommend wearing pants for the upper elevations on the Wailupe Loop. You’ll see why as the trail gets more overgrown, the higher it gets.
The pants below are my recommendations that hold up the best with the overgrowth here in Hawaiʻi, but with any hiking pants that need to be durable, make sure that they are at or near 100% nylon. This is really the most important factor!
As the trail approaches the Upper East-West junction just below the summit, the East Middle Ridge gets fairly steep once again on this final ascent.
This is one of the steeper sections up the East Middle Ridge just prior to the upper junction.
Upper Wailupe East-West Middle Ridge Junction
Once the East Middle and West Ridge Trails come together, the Wailupe Summit is only 0.1 miles (0.2 km) up the ridge.
Wailupe Summit
The Wailupe Summit is roughly 2,580 ft. (786 m), and on a clear day, you can see across much of Oʻahu’s east side, including Mt. Olomana, the Lanikai Pillboxes, and even as far as Mokoliʻi!
West Wailupe Middle Ridge
Once back at the Upper East-West junction, go right to begin the West Wailupe Middle Ridge Trail.
You may notice from the photo below that the West Ridge (right side) looks much shorter that the East Ridge (left side), and it’s for exactly this reason that I always choose to go down the West Ridge instead of up, as the shorter distance inevitably means that it’s much steeper in comparison.
Just like Kaunaʻoa above, Hulumoa is another native parasitic plant that I found growing on this ʻŌhiʻa lehua tree.
It doesn’t take long for the West Middle Ridge to noticeably descend lower than the adjacent East Ridge on the left.
It’s always nice to see a bunch of Alaheʻe trees on this trail, such as these!
When the West Middle Ridge nearly reaches the bottom of the valley, the trail will make a hard right turn, which will be immediately followed by a large Cook Pine forest.
That being said, this turn and the sections that immediately follow is what makes the Wailupe Loop Trail one of the most confusing hikes to navigate back in the dark should you choose to treat Wailupe as a sunset hike.
When the trail reaches this clearing, go straight across to find where the trail continues down to the stream.
When you get to the stream, don’t cross, but rather, follow it shortly until you see the trail that cuts away to the left.
When the trail reaches the same stream for the second time, cross over to find the trail continuing through the bamboo forest on the far side.
Following the bamboo forest, the Wailupe Loop Trail will follow the most obvious path through the bottom of the valley until you reach the same East-West junction from earlier.
Wailupe East-West Middle Ridge Junction
This is the same East-West junction from the beginning of this article, roughly 0.5-0.6 miles (0.8-1.0 km) away from the trailhead.
Native Plants on the Wailupe Loop Trail
Compared to other trails in the southern Koʻolau Mountains, such as Kuliʻouʻou Ridge, the Wailupe Loop Trail is one of the more native trails in the area once out of the lower forest.
On the upper-middle ridges, you can expect to see native plants like Uluhe, Koa, ʻŌhiʻa lehua, Alani, Kōlea, Lama, Kokolau, and Kōpiko, to truly name only a few.
If you'd like to learn more about identifying these and tons of other native plants from across the Hawaiian Islands, I encourage you to scroll through my separate article linked below.
Read My Separate Post: Native Hawaiian Plant Guide
