Five Fantastic Hikes in Oahu

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!

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.

Photo and below left photo by Heather Holt

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.

Photo by Heather Holt

Photo by Heather Holt

Photo by Heather Holt

Photo by Heather Holt

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.

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.

Photo by Heather Holt

Photo by Heather Holt

Photo by Heather Holt

Photo by Heather Holt

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.

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?