Wiliwilinui Ridge Trail: Oahu's Best Hike - Uprooted Traveler (2023)

Lush rainforests. Layer upon layer of green mountain ridges. Sweeping views of the Pacific Ocean. You can experience all of these things (and so much more!) along the Wiliwilinui Ridge Trail, a hike located on the eastern side of Oahu along the spine of Koʻolau Mountain range.

So if you’re looking for incredible views and a unique way to experience Hawai’i’s ethereal beauty, here’s everything you need to know about exploring the Wiliwilinui Ridge Trail, from how to get there to exactly what to expect along this incredible hike.

This post may contain affiliate links. If you make a purchase through them, we may receive a small commission, for which we are extremely grateful, at no extra cost to you.

• Instagram
• Pinterest
• Facebook
• YouTube
• Twitter

Pssst… are you looking for even more Oahu hikes? If so, check out our other posts about hiking in Oahu:

• 4 Actually Easy Hikes on Oahu: The Perfect Trails for Beginners
• Ehukai Pillbox Hike: The Best Hike on Oahu’s North Shore
• Koko Crater Trail: Everything You Need to Know

About the Wiliwilinui Ridge Trail

• Distance: 4.7 miles
• Elevation gain: 1,617 feet
• Difficulty: Moderate
• Dog-friendly? Yes, but only on a leash. Additionally, the trail is almost always slippery and has some steep dropoffs, so I would only recommend bringing along a very well-behaved pup!

Along this trail, you’ll hike through a lush forest up to the top of the mountain ridge and climb along the spine to its summit, providing panoramic views of the entire island of Oahu.

A significant amount of the elevation gain comes in the last half mile of the hike up to the summit, where you’ll scramble up a series of steep stairs, constructed only of thick slabs of wood and the slippery clay that covers the mountainside. While there’s no technical skills required, given its steepness and the constantly muddy terrain, the trail is definitely challenging, especially for beginner hikers.

Many of Oahu’s most stunning hikes are, similar to Wiliwilinui Ridge, along mountain ridgelines. But these epic views usually go hand in hand with danger- ridgelines are usually very narrow, with crumbly cliffs and steep, slippery ascents. And this is no joke- more than a dozen hikers have fallen to their deaths in the past decade from hikes around Oahu.

Wiliwilinui Ridge, on the other hand, is an excellent alternative to include in your Oahu itinerary as compared to other ridgeline hikes on the island- the trail is well-maintained and fairly wide, therefore providing a safer way to enjoy those fantastic vistas.

But be careful- any hike, even Wiliwilinui Ridge, comes with its own risks, especially if the trail is wet and slippery (which, on the eastern side of Oahu, is pretty much always). I’d recommend checking the weather before you go and planning your hike to avoid any rain showers.

How to Get to the Wiliwilinui Ridge Trail

This trail is unique in many ways, including the fact that it’s tucked away in an upscale gated community in the hills overlooking Honolulu.

To reach the trailhead (located here), you’ll need to pass by the security guard at the Waialae Iki 5 community. There’s only a handful of parking spots for hikers near the trailhead, so the guard passes out a certain number of laminated parking passes each day.

If the parking permits are all in use, you won’t be allowed to drive in the community and you’ll either need to come back at a later time or, alternatively, park in the residential neighborhood outside of the Waialae Iki 5 community (be sure to check for “No parking” signs!).

If you choose the latter option, you’ll need to walk at least another 1.8 miles (roundtrip) from the guard station, up a steep and winding hill to the trailhead. So if you want to be sure to snag a parking pass, you may want to time your visit for when the trail is less busy, like early on a weekday.

When my husband, Justin, and I came here, the guard also told us to try to be off the trail before dark, so I’d also avoid arriving too close to sunset. For what it’s worth, I was really nervous about not being able to get a permit (I really wanted to do this hike!), but, on a perfectly lovely Saturday afternoon, there seemed to be plenty of parking spots available at the trailhead. So perhaps the Wiliwilinui Ridge, despite its out-of-this-world beauty, is still flying somewhat under the radar.

If you’re lucky enough to snag a pass, there will be a map and clear directions on where to park included on the permit. You’ll basically follow Laukahi Street all the way to where it ends on Okoa Street, turn left on Okoa and follow the street up to one of the two small lots by the trailhead. And once you’re done with your hike, you’ll return the permit in a dropbox by the right side of the guard station.

There have been a few intermittent reports on AllTrails that the guards are only providing permits to individuals with a valid Hawai’i driver’s license or military ID. It looks like this requirement is incredibly sporadically enforced (i.e., there’s plenty of folks, including myself, who have hiked the trail and reported they were issued a permit without having these forms of ID), but just want to make you aware in case you happen to come across a particularly stringent guard.

What to Expect Along the Wiliwilinui Ridge Trail

Once you’ve arrived at the trailhead, the hike starts down a shaded dirt path that winds through dense trees. As you climb higher and higher, you’ll catch glimpses of the surrounding mountain ridges and the Honolulu skyline through the trees, providing you a taste of the amazing views awaiting you at the summit.

The trail will eventually spit you out along the ridgeline and about 1.7 miles in, you’ll reach the first of many stairs you’ll take to climb up the rest of the mountain (So. Many. Stairs). While climbing stairs for almost a mile sounds quite terrible, they help you gain elevation at a much faster clip (as compared to if you were just trudging up switchbacks), so, really, it’s just getting you to those views quicker!

There’s some sections where the stairs have eroded away or are broken, where the trail consists of little more than a slick lump of clay. Certain steeper areas have ropes to help you scramble up, while there’s other spots along the hike where you have to get a bit creative to maneuver your way up the mountain (i.e., my hands got pretty dirty from scrambling up the muddy trail here- I would not recommend wearing your Sunday best on this one).

The farther up you climb, the more stellar the views get, until eventually, you’ll see layer after layer of green mountain ridges sprawling out from under your feet and unfurling towards the Pacific Ocean. I hike a LOT in some incredibly beautiful places and this still takes the cake for the most beautiful hike I’ve ever been on!

As a friendly reminder, please be sure to understand and follow the Leave No Trace principles while you’re on the trail, particularly disposing of waste properly (pack it in, pack it out) and leave what you find (take only memories, leave only footprints).

Hawai’i has a complicated history, especially with the United States, with the U.S. invading and overthrowing the Hawaiian monarchy in the late 1800s and exploiting its land and people ever since (if you want to learn more, here’s a helpful article regarding the colonization of Hawai’i). If you’re a visitor here, it’s imperative to respect Hawai’i’s beautiful culture, history, and land.

What to Bring on the Wiliwilinui Ridge Trail

Since this trail isn’t particularly long, there isn’t a ton you’ll need to conquer this hike, but there are a few things you should definitely make sure are on your Hawaii packing list.

• Headlamp: If you, like me, want to watch the sunset along the ridgeline, you NEED to bring along a headlamp to make your way back down the trail (note that, if you’re interested in watching the sunset here, the parking permits are only good during the daylight hours, so you’ll have to be thoughtful about where you watch sunset and how quickly you can safely make it back down to your car afterward).

  During our time in Oahu, we went on several sunset hikes, including the Koko Crater Trail and Ehukai Pillbox Hike, and on each one, ran into a terrified hiker fumbling their way back down the trail, either with a very weak cell phone flashlight or without any kind of lighting source to help them at all.

  Please don’t be that guy, especially on this trail, where you’re walking along the thin spine of a steep mountain- hiking a trail in the dark without the appropriate gear is extremely dangerous and could result in you doing anything from twisting your ankle to literally falling off a cliff (definitely not how you want to remember your Hawaiian getaway).

  My husband, Justin, and I have these ones that came in a pack of two AND are rechargeable, so you don’t have to mess around with carrying extra batteries. Score!

• Hiking shoes: While most people laze around Oahu with flip-flops, I strongly would advise against doing that on this trail, given the steep and uneven terrain and slippery, muddy ground. At a minimum, you should wear hiking sandals, like Tevas (options for women and men) or Chacos (options for women and men), to provide better traction and support.

  I wore actual hiking boots (here’s my boots and men’s equivalent) and personally think, if you’re planning on doing this and other moderately challenging hikes in Hawai’i, it’s 100% worth the luggage real estate to bring along some sturdier shoes.

• Reusable water bottle: Be sure to bring along plenty of water on this hike- while parts of the trail are shaded and the air along the mountain ridge feels cooler, you’re literally going to be climbing stairs for about a mile under the hot Hawaiian sun- so hydrate up!

  To be kind to the planet and to cut down on wasting money on bottled water, Justin and I both have giant Nalgene bottles that we take everywhere, from international vacations to RV trips around the Pacific Northwest and, yup, even hiking in Hawai’i!

• Clothes that you don’t mind getting dirty: Between scrambling up sections of the trail that don’t have stairs and unintentional slips (Justin and I both slipped and fell along the muddy trail), you will almost certainly get filthy along this hike.

  Another fun fact: the mud here will stain your clothes! Justin wore a new white t-shirt while doing this hike that was ruined from the red clay that got on it during one of his falls. So perhaps plan on wearing some non-white apparel.

I hope you have an incredible time hiking the Wiliwilinui Ridge Trail. Are there any other tips for this hike that I forgot to include here? Let me know in the comments below!

Thank you for reading our post! Check out our latest stories here and follow us on Instagram (@UprootedTraveler), YouTube, or on Facebook to see what we’re up to next!