Hiking the Wailupe Loop Trail on Oʻahu

Distance: 5.0 miles / 8.0 km

Located between both Wiliwilinui to the north and Hawaiʻi Loa Ridge to the south, the Wailupe Loop Trail feels like a hidden gem compared to the surrounding trails that often attract more visitors.

On a different note, 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 Trail Map

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

Wailupe Loop Trailhead Parking

Wailupe Loop Trailhead Parking

 

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.

Wailupe Loop Trailhead

Wailupe Loop Trailhead

Then, the Wailupe Loop Trail will follow this path through the bottom of the valley for roughly the next 0.5 miles (0.8 km).

Wailupe Loop Trail

Wailupe Loop Trail

Wailupe Loop Trail

Wailupe Loop Trail

Wailupe Loop Trail

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 additional splits on the right-hand side of the trail before East Middle.

Wailupe East-West Middle Ridge Junction

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.

East Wailupe Middle Ridge Crossover

Initially, the crossover will drop down.

East Wailupe Middle Ridge Crossover

East Wailupe Middle Ridge Crossover

East Wailupe Middle Ridge Crossover

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.

East Wailupe Middle Ridge Crossover

East Wailupe Middle Ridge Crossover

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 Crossover

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.

East Wailupe Middle Ridge

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.

Go Right

East Wailupe Middle Ridge

East Wailupe Middle Ridge

East Wailupe Middle Ridge

East Wailupe Middle Ridge

On such a steep trail, the views of ʻĀina Haina come quick!

East Wailupe Middle Ridge

Looking Back

However, after the initial steep climb out of the valley the East Middle Ridge levels off, as it climbs a much more gradual slope than the beginning.

East Wailupe Middle Ridge

East Wailupe Middle Ridge

I then noticed Kaunaʻoa, an endemic parasitic vine, taking over ʻAkoko, another native Hawaiian endemic.

Kaunaʻoa - (Cuscuta sandwichiana)

East Wailupe Middle Ridge

At two different points on the East Middle Ridge, the trail will contour to the left before regaining the ridge shortly after.

East Wailupe Middle Ridge

East Wailupe Middle Ridge

East Wailupe Middle Ridge

This is the second of the two contours off the left side of the ridge.

East Wailupe Middle Ridge

East Wailupe Middle Ridge

East Wailupe Middle Ridge

East Wailupe Middle Ridge

East Wailupe Middle Ridge

East Wailupe Middle Ridge

East Wailupe Middle 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 of 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!

East Wailupe Middle Ridge

East Wailupe Middle Ridge

East Wailupe Middle Ridge

East Wailupe Middle Ridge

East Wailupe Middle Ridge

East Wailupe Middle Ridge

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.

East Wailupe Middle Ridge

East Wailupe Middle Ridge

East Wailupe Middle Ridge

East Wailupe Middle Ridge

This is one of the steeper sections up the East Middle Ridge just prior to the upper junction.

East Wailupe Middle Ridge

Upper Wailupe East-West Middle Ridge Junction

Once the East Middle and West Middle Ridge Trails come together, the Wailupe Summit is only another 0.1 miles (0.2 km) up the ridge.

Upper Wailupe East-West Middle Ridge Junction

Wailupe Loop Trail

Wailupe Loop Trail

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 near Kualoa Ranch to the north!

If you are interested in continuing further on the summit trail, some of the notable summits to the north include Wiliwilinui Ridge and Mauʻumae Ridge (Puʻu Lanipō); and some of the notable summits to the south include Hawaiʻi Loa Ridge, followed by Kūlepeamoa.

Read My Separate Post: Koʻolau Summit Trail (KST)

Wailupe Summit

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 than 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.

Go Straight (Right)

West Wailupe Middle Ridge

West Wailupe Middle Ridge

West Wailupe Middle Ridge

West Wailupe Middle Ridge

Just like Kaunaʻoa above, Hulumoa is another native parasitic plant that I found growing on this ʻŌhiʻa lehua tree.

Hulumoa / Hawaiian Mistletoe - (Korthalsella complanata)

West Wailupe Middle Ridge

West Wailupe Middle Ridge

It doesn’t take long for the West Middle Ridge to noticeably descend lower than the adjacent East Ridge on the left.

West Wailupe Middle Ridge

It’s always nice to see a bunch of Alaheʻe trees on the trail!

West Wailupe Middle Ridge

Alaheʻe - (Psydrax odorata)

West Wailupe Middle Ridge

West Wailupe Middle Ridge

West Wailupe Middle Ridge

West Wailupe Middle Ridge

West Wailupe Middle Ridge

West Wailupe Middle Ridge

West Wailupe Middle Ridge

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.

Go Right

West Wailupe Middle Ridge

West Wailupe Middle Ridge

Wailupe Loop Trail

When the trail reaches this clearing, go straight across to find where the trail continues down to the stream.

Go Straight

Wailupe Loop Trail

When you get to the stream, don’t cross, but rather, follow it down a short distance until you see the trail that cuts away to the left.

Wailupe Loop Trail

Wailupe Loop Trail

Wailupe Loop Trail

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.

Go Straight

Wailupe Loop Trail

Wailupe Loop Trail

Wailupe Loop Trail

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 Loop Trail

Wailupe Loop Trail

Wailupe Loop Trail

Wailupe East-West Middle Ridge Junction

This is the same East-West junction from the beginning of this article, located roughly 0.5-0.6 miles (0.8-1.0 km) away from the trailhead in ʻĀina Haina.

Wailupe East-West Middle Ridge Junction

PAU!

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 would like to learn more about these and many 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

Kōlea lau liʻi - (Myrsine sandwicensis)

@noahawaii

Hi,

Iʻm a self-taught adventure photographer living on the island of Oʻahu.

@noahawaii

https://noahlangphotography.com/
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