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I’ve said it before, and in all likelihood I’ll say it many more times — one of my favorite things about Hawaii is that life is lived outdoors. Sure, I slept in a room with four walls and roof (most nights!) but my days were spent surfing, diving, ATV-riding — and hiking.

I never considered myself much of a hiker before this trip, but in Hawaii I found myself enthusiastically strapping on my sneakers and nodding “yes” to every trekking suggestion. And it all started in Oahu, with these five easy to moderate trails. Taking place on every corner of the island, they run the gamut from coastline excursions with postcard ocean views to muddy jungle hikes with waterfall rewards. Join me on this hiking tour around Oahu!

Hiking Lighthouse Trail, Oahu

Diamond Head

Total length: 1.6 miles roundtrip (Hiking times are obviously highly subjective and based on many factors. The State Park recommends allowing two hours for this trail, it took us less than an hour with plenty of time for photography.)
Difficulty:
Easy
Terrain: Hot, dry slopes
Location: East of Waikiki, entrance off Diamond Head Road between Makapu’u Ave and 18th Ave
Note: Entry fee of $5 per vehicle or $1 per walk-in visitor.

Oahu’s best known landmark, Diamond Head is actually a crater formed by Hawaii’s famous volcanic activity. Over the years it has been used as a site for sacred Hawaiian rituals, a US army base, and now a popular tourist attraction. In the 1700’s, Western explorers mistook the calcite crystals in the crater for diamonds, hence the name Diamond Head.

Getting to the trail summit means driving through a tunnel into the parking lot in the middle of the crater. The walk up to the ridge is a peek into the geological and military history of Oahu. The walk is a glimpse into the geological and military history of this volcanic crater. After a short flat walk across the middle of the crater, switchbacks traverse up the interior crater wall. There are stairs and railings to help you along, and at one point you pass through a lighted tunnel. The trails can be very steep and hot as there is no shade covering, but the short distance keeps it from being too challenging.

From the summit bunkers on the crater rim, you are gifted 360-degree views of the Southeast coast, from Koko Head crater to the Wai’anae mountain range. For photography purposes, it’s best to visit in the morning. We visited in the afternoon, and the stunning views over Waikiki and Honolulu were backlit.

Hiking Diamond Head

Hiking Diamond Head

Hike Oahu
Hike Oahu

Hiking Diamond Head

Hiking Diamond HeadPhoto and below left photo by

Hike Oahu
Hike Oahu

Hiking Diamond Head

Hiking Diamond Head

Hiking Diamond Head

Ka’ena Point

Total length: 5 miles roundtrip (from the end of Highway 930 to the Northwesternmost tip and back)
Difficulty:
Easy
Terrain: Flat open coastline
Location: The end of Highway 930, Northwest Oahu
Note: There is a second entrance to the trail from the end of Highway 93 (if arriving from Waianae). From one entrance to the trail to the other, the distance is 3.5 miles.

This hike has the distinction of bringing you to the isolated Northwesternmost tip of Oahu. You can reach the point either from the Leeward side, via a trailhead at the end of Highway 93, or from the North Coast, via a trailhead at the end of Highway 930. We took the North Shore route.

The trail follows an old railroad bed, and thanks to the flatness is also great for mountain biking. Despite the length, the lack of elevation change makes this an easy hike that we completed in just over two hours. We found the first two miles or so to be a bit monotonous, walking on flat earth with mountains on one side and ocean on the other, until we entered the 59-acre Ka’ena Point Natural Area Reserve. Here the trail becomes sandy and slightly more challenging. This fenced-in area is home to endemic and indigenous plants, nesting seabirds, Hawaiian monk seals, and even humpback whales (in the winter!)

Unfortunately we missed out on Ka’ena Point’s beautiful views of the Wai’anae Mountain range due to heavy cloud coverage. Still, we were rewarded for our exertion by an amazing show put on by some playful monk seals.

Hiking Ka'ena PointPhoto by

Hiking Ka'ena Point

Hiking Ka'ena Point

Hiking Ka'ena Point

Hiking Ka'ena Point

Hiking Ka'ena Point

Hiking Ka'ena PointPhoto by

Hike Oahu
Hike Oahu

Hiking Ka'ena Point

Hiking Ka'ena PointPhoto by

Hiking Ka'ena PointPhoto by

Makapu’u Point Lighthouse Trail

Total length: 2 miles roundtrip
Difficulty:
Easy
Terrain: Hot, Dry Slopes
Location: The park and trailhead are located off of the Kalanianaole Highway (Hwy. 72) at the Southeasternmost point of Oahu

I hiked the Lighthouse Trail at sunset on the day I arrived in Oahu, with the lei still fresh around my neck. The trail, encompassed within the Ka Iwi State Scenic Shoreline, provides scenic views of O‘ahu’s southeastern coastline, including Koko Head and Koko Crater. Signs along the trail hinted that this is an excellent spot for humpback whale spotting, had I visited in the right season (November-May). The path follows a gradual but distinct incline up to the summit.

At the trail’s final destination at Makapu‘u Head, the views of the Windward Coast and it’s offshore islets are beyond reward for the work it took to get there. There are also views of the historic Makapu‘u Lighthouse, built in 1909. The sun was setting by the time I got there, but supposedly on a clear day you can see all the way to Moloka‘i.

Hiking Lighthouse Trail, Oahu

Hiking Lighthouse Trail, Oahu

Hike Oahu
Hike Oahu

Hiking Lighthouse Trail, Oahu

Hike Oahu
Hike Oahu
Hike Oahu
Hike Oahu

Hiking Lighthouse Trail, Oahu

Maunawili Falls

Total length: 3.2 miles roundtrip
Difficulty:
Moderate
Terrain: Muddy Jungle, with Many Streams
Location: From Kalanianaole Hwy, turn onto Auloa Road into a small residential neighborhood. Look for trailhead sign.
Note: Bring your pup! This is the first dog friendly hike on this list. Also, get clear directions, as finding the trail head can be tricky if you’re unfamiliar with the area.

This trail has the distinction of being one of the few reliable waterfalls on Oahu, providing a year-round show and never drying up. It also has the accolade of being host Wim’s favorite hike on the island, and a fairly well-kept secret, considering it’s not even in Lonely Planet!

We started this jungle trek inconspicuously, parking in a suburban neighborhood. Passing a battered trailhead sign, we were soon thick in the hot tropical wilderness. The trail is muddy, and we crossed the river several times along the trail. Either wear shoes you don’t care about or be prepared to throw them in the washing machine like we did after.

This trail ascends slowly but surely, and half way through it breaks out of the trees for some rewarding views of the surrounding mountains and ocean in the distance. Back into the jungle, we eventually reached our destination — the falls themselves. The pools are small but deep and locals love to take daring jumps off of various ledges. Normally an adrenaline junkie, I was content to just watch! We did however swim across the pool and climb up the falls to another smaller waterfall above the main falls. Scary-looking signs along the trail warn of Leptospirosis; a flesh-eating bacterial infection found throughout the tropical fresh waters of Hawaii. If you have any open wounds, best to play it safe and avoid swimming here.

Hiking Maunawili Falls

Hiking Maunawili Falls

Hiking Maunawili Falls

Hiking Maunawili FallsPhoto by

Hiking Maunawili FallsPhoto by

Hiking Maunawili FallsPhoto by

Hiking Maunawili FallsPhoto by

Hiking Maunawili Falls

Hike Oahu
Hike Oahu

Lanikai Pillbox Trail

Total length: 1.2 mile roundtrip
Difficulty:
Moderate
Terrain: Hot, Crumbly Dry Slopes
Location: The trailhead is marked by a small sign on a no-name street branching off Ka’elepupu Drive, directly across from the Mid-Pacific Country Club
Note: A full loop of 3.1 miles can be hiked by continuing on past the second bunker, bringing you back down to Aalapapa Drive where you walk along the main road back to your car. This trail is also dog friendly.

The Lanikai Pillbox Hike, also known as the Kaiwa Ridge Trail, was my favorite Oahu hike for its picturesque views over Lanikai Beach and the colorful graffiti of the pillbox bunkers.

Like Maunawili Falls, this hike wasn’t in my guidebook and started from a quiet residential street. It starts off surprisingly strenuous, as the trail is steep and the ground loose for the first ten minutes. After that things level off a bit, though there are still steep drops offs over the ridge. Of course, we might have had an easier time had we not been wearing flip-flops. Trotting along the ridges, we were treated to views of the Mokulua Islands, Kailua Beach, Lanikai Beach and the surrounding residential neighborhood.

Our destination was two pillbox bunkers erected during World War II. Their location was strategic — they provide sweeping views of the Windward coast. We found the bunkers are still being used for surveillance today — a local marine biologist was using one as a lookout point to study illegal fishing methods in the surrounding bays. We were completely smitten with the colorful and fun graffiti covering the pillboxes. My favorite? A chuckle-inducing “Aloha, junkies!” scrawled across the inside of one of the bunkers — a nod to the somewhat seedy look of the abandoned concrete structures.

Hiking Pillbox Trail

Hiking Pillbox Trail

Hike Oahu
Hike Oahu

Hiking Pillbox Trail

Hiking Pillbox Trail

Hiking Pillbox Trail

Hiking Pillbox Trail

Hiking Pillbox Trail

Hike Oahu
Hike Oahu

Hiking Pillbox Trail

This is by no means an exhaustive list of hikes in Oahu — but it is a start. I found Hawaii to be at its most inspiring when I was out exploring it by foot with a camera in hand! I can’t wait to return to Oahu someday and revisit these old favorites, while trying out new more challenging trails as well. Stay tuned for some of the major hikes I took on in Maui and Kauai!

Have you been hiking in Oahu? Do you have any trails I have to try out?

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49 Comments...
  • Sebastian @ Off-The-Path.com
    November 20 2012

    One word: Stunning!!!
    Sebastian @ Off-The-Path.com recently posted..

    • Meihoukai
      November 20 2012

      Thanks Sebastian! They were even better in person 🙂

  • Kent @ NVR
    November 20 2012

    You know we’re big hikers, so this is a fantastic resource. We loved that Diamond Head hike, but there was a non-stop line of people when we were there.

    • Meihoukai
      November 20 2012

      I feel so lucky to have visited Hawaii in the shoulder season, when crowds were pretty low. Still, Diamond Head was BY FAR the most crowded of these hikes!

  • Rob
    November 20 2012

    Amazing!!

  • Ashley of Ashley Abroad
    November 20 2012

    I want your life!

    Also I love your photos of the Lanikai Pillbox Trail… the colors are so vibrant.
    Ashley of Ashley Abroad recently posted..

    • Meihoukai
      November 20 2012

      Heather, who is a professional photographer, didn’t take her camera on that hike and she was KICKING HERSELF. It was so beautiful!

  • Pete
    November 20 2012

    Well you sold us on hiking in Oahu. The Kaena Point 10 photo is just wow.
    Pete recently posted..

    • Meihoukai
      November 20 2012

      Yay! I’m glad to hear it. I did amazing hikes on Maui and Kauai as well… can’t wait to share those.

  • Lindsey
    November 20 2012

    These hikes look amazing 🙂 I especially love the Maunawili Falls hike.
    Lindsey recently posted..

    • Meihoukai
      November 20 2012

      They really were Lindsay! Maunawili was definitely the most unique out of these, simply because it brought us away from the coast and into the heart of the island!

  • Ayngelina
    November 20 2012

    You are wearing flip flops in some of those photos, now that is my kind of hiking!
    Ayngelina recently posted..

    • Meihoukai
      November 20 2012

      Yup, I wore flip flips to Diamond Head and on the Pillbox Trail. On Diamond Head it was totally fine to do so (though there were tons of people in proper hiking shoes), but on Pillbox Trail it was stupid. Definitely need sneakers for that one!

  • Shaun
    November 21 2012

    Amazing photos! real talent in there. I like the pillbox trail and the photos of the seals.

    • Meihoukai
      November 22 2012

      Thanks Shaun! Though I admit I can’t claim credit for the seal photos. Thank God for Heather and her zoom lens!

  • You never, ever disappoint, you know that? What a great source of info this post is and the pics amazing as always!!! I never really got the chance to hike on Oahu as I was too busy driving around the island or diving, but I know I will one day!
    Andi of My Beautiful Adventures recently posted..

    • Meihoukai
      November 22 2012

      You are so sweet Andi! Sounds like your experience on Oahu was similar to mine on the Big Island… I felt like I was in the car the whole time!

  • Erica
    November 21 2012

    Wow! These pictures are gorgeous Meihoukai! It really makes me miss being on the beach.
    Erica recently posted..

    • Meihoukai
      November 22 2012

      Thank you so much Erica! You guys are great photographers, so I appreciate it!

  • Chrystal McKay
    November 21 2012

    Oh My Gosh. These look INCREDIBLE. I’ve never really thought of Hawaii as somewhere I’ve wanted to visit. But these hikes look spectacular. Hiking is one of my FAVOURITE things! Thanks for this article now I think I might go to Oahu for those views alone. AMAZING.
    Chrystal McKay recently posted..

    • Meihoukai
      November 22 2012

      So glad to hear I’ve put Oahu on your radar, Chrystal 🙂 There are amazing hikes on Maui and Kauai as well… stay tuned!

  • Emily in Chile
    November 21 2012

    Sadly we didn’t even hike Diamond Head when we were on Oahu, since there were so many other fun things we wanted to do. Next time for sure!
    Emily in Chile recently posted..

    • Meihoukai
      November 22 2012

      Diamond Head is one of those things I think you’ve just got to check off the list. To be honest I think the rest were more impressive.

  • TammyOnTheMove
    November 21 2012

    Looks stunning. I never had Hawaii down as a hiker’s paradise. I particulalry like the trek to the Maunawili Falls. Looks like you are trekking with Indi to find an archeological treasure. 🙂
    TammyOnTheMove recently posted..

    • Meihoukai
      November 22 2012

      Hawaii is absolutely a treasure chest for hikers! I think it’s one of its greatest assets.

  • Koren @ City Gal
    November 30 2012

    I love these photos, and thank you for rating the difficulty-level, so I can stay away from anything not marked easy! 🙂
    Koren @ City Gal recently posted..

    • Meihoukai
      November 30 2012

      Difficulty ratings are definitely key 🙂 Gotta know what you’re getting yourself into!

  • Jenna
    December 11 2012

    Love the photos! We hiked Diamond Head and Maunawili Falls awhile back. We really enjoyed both, but now I’m wishing we would have had time to do more of these! Especially Ka’ena Point-it looks beautiful! Also, good point about getting good directions for Maunawii Falls–we had some trouble finding the right path, but eventually made it, lol!
    Jenna recently posted..

    • Meihoukai
      December 11 2012

      I’m impressed you went to Maunawili Falls Jenna, considering it wasn’t in my guidebook! How did you find out about it? I never would have known if not for my host extraordinaire Wim!/

      • Jenna
        December 12 2012

        I can’t remember exactly what the website was, but I found it online when I was researching hikes on Oahu. It was a pretty outdated site at the time, so I’m not even sure if it’s still around, but we just decided to go for it anyways and give it a try! Our directions weren’t that great, but thankfully we figured it out 🙂 It must have been fun to have a friend there–it looks like you got to do a lot of awesome things!
        Jenna recently posted..

        • Meihoukai
          December 13 2012

          That is so cool, Jenna! Kudos to you for being so pro-active and seeking out something off the beaten path.

          • Frank
            January 15 2013

            Glad to see that my two favorite hikes from when I grew up on Oahu made it to the list! I used to live in Kailua and would do that Maunawili Falls hike(I used to live in that neighborhood) and the Lanikai Pillbox hike all the time. Great pictures, the view are fantastic right!? Please tell me you did jump off the rocks into the waterfall : )

          • Meihoukai
            January 15 2013

            Actually, I did not do this jump! Some local guys were going wild with it and I think I got a little intimidated 🙂 Next time!

  • dragao
    March 14 2013

    The asian girl is very pretty! Would love to hike with her!

  • [email protected]
    May 17 2013

    Beautiful scenery throughout your hikes! I love the picture of the seal popping it’s head out of the rushing water, cute! Thanks for sharing your tips and travels. Good luck with future hikes!
    [email protected] recently posted..

    • Meihoukai
      May 18 2013

      Thanks Lauren! I had a lot of fun writing this post. I wish I was back in Hawaii right now, I miss these trails!

  • Diane
    February 22 2014

    I love living on Oahu and exploring the amazing variety of hikes on this island! I have done your 5 and so many more!

    • Meihoukai
      February 24 2014

      Hey Diane! I hope to by returning to Oahu soon… if so maybe I can do a follow up to this post 🙂 I love Hawaii!

  • Angeelika
    January 13 2015

    Amazing pictures and blog! I’m so glad that I found your blog, as I’m going to Hawaii in 2 months 🙂
    Angeelika recently posted..

    • Meihoukai
      January 15 2015

      Lucky you, Angeelika 🙂 I LOVE Hawaii. Have fun!

  • Robert
    February 4 2015

    I just did the Diamond Head hike today. It was beautiful.

    • Meihoukai
      February 6 2015

      I miss Hawaii, Robert! Would love to do that hike again.

  • gail olsen
    August 2 2015

    What beautiful pictures,was in Hawaii but in no condition to do hiking.Watching these it made me feel like I made that journey.

    • Meihoukai
      August 5 2015

      I’m happy to hear that you could come along virtually, Gail!