Hiking the Wailupe Loop Trail on Oʻahu, Hawaiʻi
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 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
My Hawaiʻi Hiking Checklist
Osprey 3L Water Bladder - The Osprey 3L water bladder is the most universal hiking and backpacking water bladder on the market, and it’s my go-to because of the slide-off seal that allows it to be quickly filled from the top. Additionally, individual parts are easily replaceable, such as the bite valve.
Blister / Heel Protectors - I swear by these cheap, amazing heel protectors to prevent blisters for nearly every kind of hiking and backpacking that I do!
Black Diamond Headlamp - Personally, I recommend the Black Diamond Storm because it is one of the brightest, lightest, and longest-lasting headlamps on the market—and trust me, the weight-to-battery-life ratio really does matter!
Hiking / Trail Running Shoes - Depending on the type of trail, I prefer to use either the Keen Targhee for longer, more rugged hiking or the HOKA Zinal Trail-Running Shoe for lighter, less intense trails. In either case, both have been amazing to me for many years across countless environments, and both can be found in men’s and women’s sizes. - (Men’s Keen / Women’s Keen) (Men’s HOKA / Women’s HOKA)
Waterproof Rain Shell - You never know when it may rain, and I’ve learned over the years that a rain shell is far better than a rain jacket. By this, I mean that it’s best to have something that the water will roll right off of, which is why I recommend the Patagonia Torrentshell 3L available in both men’s and women’s sizes.
High SPF Sunscreen - Packing high-SPF sunscreen is a must for long days outside!
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 0.5 miles (0.8 km).
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.
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, as it climbs a much more gradual slope than the beginning.
I then 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 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!
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 Middle Ridge Trails come together, the Wailupe Summit is only another 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 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)
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.
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 the trail!
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 down a short distance 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, located roughly 0.5-0.6 miles (0.8-1.0 km) away from the trailhead in ʻĀina Haina.
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
More Oʻahu Adventures
If you’re interested in reading about some more amazing Oʻahu adventures, check out my separate posts below!
Best Hotels & Restaurants in Waikīkī
If you’re trying to decided where to stay on Oʻahu, check out my top 10 list for the best resorts and restaurants in Waikīkī.
I break down what makes one hotel a better choice over another, so that you can find the best fit for your stay on the island.
Read My Separate Post: Best Waikīkī Hotels & Restaurants
Waikīkī
HNL Airport-Hotel Shuttle
Prices on ride-share apps like Uber/ Lyft cannot beat the price of booking your hotel shuttle prior to arrival. I say this because there are additional fees for ride-share airport pick-ups at Honolulu Airport (HNL), which is why I recommend booking your transportation in advance using the options below.
Additionally, the last option below will go as far as the Ko ʻOlina Resorts on the West Side and Turtle Bay on Oʻahu’s North Shore!
Best Way to Book Rental Cars!
I travel quite a bit, and I know firsthand that finding a good rental car deal can be a challenge, but that’s why I recommend comparing all of your options with Discover Cars.
In short, Discover Cars is a well-known, reputable business that allows you to search for the best deal across companies, and they have the best full-refund cancellation policy I’ve ever seen, valid up to 72, or sometimes even 48, hours prior to your reservation!
Book Here: Discover Cars
Oʻahu
Visiting Other Islands
If you are visiting Oʻahu or heading to another island, check out some of my personal recommendations for Oʻahu, Maui, Kauaʻi, Molokai, Lānaʻi, and Hawaiʻi Island (Big Island) in these separate posts.
If you’re trying to decide which island is right for your visit, check out my overview about each island in the post below.
Read My Separate Post: What is the Best Hawaiian Island to Visit?
What is the Best Time of Year to Visit Hawaiʻi?
The weather in Hawaiʻi can often appear to be warm and beautiful throughout the year, but in my experience, there is a lot more to consider when planning what time of year to visit the islands, such as what island you are considering, what sides of each island do you plan to stay, what activities are you most interested in, the wildlife, and countless other nuanced variables that can all impact the type of trip you can expect to have.
For these reasons, I highly recommend reading through my separate article to not only understand my thoughts regarding the best time of year to come to Hawaiʻi but also what you need to consider based on the time of year that you plan to visit.
Read My Separate Post: What is the Best Time of Year to Visit Hawaiʻi?
10 Best Tours & Excursions on Oʻahu
There are a lot of different tour options to choose from on Oʻahu, but to make it easier to decide, I made a list of my favorite tours because some things simply are better with a local guide!
Read My Separate Post: Best Tours on Oʻahu
Oʻahu
Safety
All hikes in Hawaiʻi should not be compared to trails outside of the islands, and hikers should exercise due caution on every adventure, given that many are extremely dangerous.
By this, I mean that Hawaiʻi is known for hot, humid weather, steep, dramatic, and unstable cliffs, and flash floods, which can occur without warning. Therefore, it is important that you check the local forecast, understand the physical condition of your entire group, and pack sufficient food and water before attempting any adventure.
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