FitTravelingMama O‘ahu Hiking Guide
Updated: Oct 13, 2018
I’ve heard people say they get “island fever” while living in Hawai‘i. After completing dozens of hikes throughout O‘ahu, I simply don’t understand how anyone could feel that “the rock” is too small for them.
When I’m on top of ridge looking down at the mountains all the way to the vast Pacific Ocean, I feel so small in comparison. It’s a reminder that although O‘ahu is the most populated island in the chain with roughly one million people, so much of it is still wild and uninhabitable.
There are more than 100 hikes in the valleys and ridges of O‘ahu’s two mountain ranges, the Ko‘olau and the Wai‘anae mountains. Each hike is unique in its terrain, degree of difficulty and even the climate. For example, hikers will find cacti and a desert climate on all sides of the island, while hikers may encounter a rainforest climate and waterfalls on the same trail a few miles away. This spectacular climate diversity is shared by all the Hawaiian Islands, which is what captivated me to put down roots in Hawai‘i’s paradise.
I challenge those with Island fever to try a few of my favorite hikes below and reconsider their “diagnosis.”
Makapu‘u Lighthouse Trail:
This paved trail on the southeastern tip of the island is perfect for an uphill stroller workout or to catch a sunrise (or both if you’re really ambitious!) before breakfast and the beach. The 1-mile steep ascent has lovely, rewarding views of the Makapu‘u Lighthouse below, white sand beaches of the East Side and the Ka Iwi southern shoreline. The coolest features about this hike are the adventures that await hikers right off the trail – such as tide pools that you can walk down to (only advised while the surf is calm) and lagoons on the southern edge that provide an opportunity for a cool dip after a hot hike in a desert-like environment. For directions and more info, click here.
Lanikai pillboxes (Ka‘iwa Ridge):
Popularized by President Barack Obama during his Hawaiian vacations, the Lanikai Pillboxes are crowded, but should not be written off as a touristy hike to avoid. Located on the windward side of O‘ahu overlooking the white sand beaches of Kailua and the offshore Mokulua Twin Islands in the prestigious Lanikai neighborhood, the approximate one-mile pillbox hike can be turned into a longer loop (about 3-4 miles) through a sahara-esque climate if you continue the hike beyond the pillboxes that eventually empties out near the end of the one-way street running southeast (A‘alapapa Dr.). Runners may prefer to add a 3-mile beachfront “Lanikai loop” into their workout by cruising over the hills on A‘alapapa Drive and heading back on the straight, flat Mokulua Drive. Catch a Lanikai sunrise on a weekday to avoid the crowds and the heat, or summit the pillboxes at day’s end to watch the sun set behind the Ko‘olau mountains. This is kid-friendly, but the first hill will be tough for keiki to climb.
If the panoramic views of North Shore and the waves spraying over the coast aren’t enough of a draw to do this hike, the amazing wild life sightseeing will be. Ideal for a sunset stroll or trail run, this 3-mile out-and-back to the westernmost point of the Island traverses along the northwestern shore of O‘ahu. Lucky hikers will see monk seals basking in the sun near the water’s edge, Hawaiian green sea turtles in the shallow tide pools and plenty of white albatross birds. Note: the trail continues to the west side toward Waianae, but part of the road has crumbled and is unsafe for passing. Click here for more info on this family-friendly hike.
One of my favorites to trail run, Aiea Loop, showcases 4.8 miles of Central Oahu’s forests. A relaxing kid-friendly hike that begins in Aiea Heights and gradually climbs to 900 feet of elevation, the loop winds through Norfolk Island pines and native Hawaiian Koa and Ohia trees. Although most of the hike’s views are within the forest, there are clearings that provide vistas of Pearl Harbor all the way to Waikiki, with one overlook over the H3 highway, the main thoroughfare from central O‘ahu to windward O‘ahu. Beware of pesky tree roots along the trail – I once sprained a finger from a bad tumble caused by these hazards!
Kokohead Crater Stairs:
Categorizing the Kokohead hike up more than 1,000 steep stairs as “moderate” is purely relative. This trek, located in Hawaii Kai on the southeast part of the Island, can be a beast to the unexperienced hiker or a typical morning routine for local fitness enthusiasts. However, it’s a must-do for any visitor for the views - and bragging rights – when a hiker reaches the top of the steps, built from World War II Era rail road tracks that lead to an old bunker and the ridgeline. Avoid doing this hike in the middle of the day as it’s extremely hot, and bring plenty of water. With a bridge in the middle containing gaps between the railroad ties, I would not recommend this hike for families with children. For those who embrace the “work hard, play hard” mentality, Kona Brewing Co. is just a few miles away at the Koko Marina Shopping Center for a refreshing reward after a grueling climb.
Less popular than mainstream waterfall hikes such as Maunawili Falls and Manoa Falls, Laie Falls is also much less crowded, but just as fun. The approximate 7-mile roundtrip out-and-back hike takes me about 4-5 hours and follows a pretty ridgeline on North Shore near the town of Laie. The waterfall at the end features a pristine pool for swimming and is overall a family-friendly hike, albeit long for little ones. Adventurous hikers may journey beyond the main waterfall to 18 smaller falls beyond, but travel with more caution on this section of the trail.
Upper Makua Cave:
Venture out to the leeward side of the Island to tackle the short (.75 miles round trip), but steep scramble up to Makua Cave. You can’t get much further west, as the trail head is off Farrington Highway past Wai‘anae and Makaha, next to the other entrance to Ka‘ena Point (referenced above). For a little climbing on all fours due to the incline, the rewarding view at the top is spectacular – and the silhouette photo opportunities with the coastline in the background are Instagram-worthy. There are sheer drops off the front of the trail, so I would not recommend this as a family-friendly hike. Makua Cave doesn’t warrant a trip out to the leeward side for the hike alone, but is nice when paired with a Wai‘anae beach day, snorkeling at Electric Beach or a trip to Ko‘olina.
Ka‘au Crater is my absolute favorite hike on O‘ahu because it has everything a hiker could want to see and experience – a ridgeline with panoramic views of the southern shoreline along the ascent AND the windward side of the Island at the summit, three waterfalls (one to physically climb up with ropes) and the novelty of hiking through an extinct Hawaiian volcano crater. I also enjoy this diverse 5-6-hour, 5-mile hike because there is an alternate route to climbing back down the waterfalls; hikers may opt for a more gradual, grassy loop to follow to the bottom if they don’t want to risk the slippery, often perilous descent. Ka‘au Crater begins in the back of Palolo Valley by the Buddhist Mu Ryang Sa Temple, and is somewhat boring for the first hour, following a pipe on a narrow muddy trail through the trees, until the first waterfall is reached. But, don’t give up because the rest of the hike is worth it! Warning: hikers will use a lot of upper body strength on this trail with the ropes, especially along the top ridgeline. Avoid hiking Ka‘au Crater during inclement weather or after a heavy rain. To read more and find the trailhead, click here.
Olomana, or “Three Peaks,” will always hold a special place in my heart. Located in the beautiful town I lived in called Kailua on the windward side of O‘ahu, I could step outside my front door and see Olomana looming above our village. It was a constant reminder of how incredible, yet challenging this hike could be! I was once climbing the three peaks with a friend, who had to turn around after the first one due to time restraints. I decided to keep going to the second and third peak on my own (not recommended), which I knew would be difficult with all of the ropes and scrambling involved. There were certainly a few close calls, but I truly felt at peace on the mountain by myself. Olomana, a 4.5-mile trail that varies in duration, begins as an hour-long climb up the first peak that doesn’t involve many ropes or climbing; just a lot of inclined cardio. For those afraid of heights, do not venture beyond the first peak. The journey beyond includes descents, then ascents up to the second and third peak. In between these peaks, the trail becomes technical with a meticulous keyhole rock formation that hikers have to maneuver around. It is possible to go down the back side of the third peak, but this takes hikers to a different trail and would involve parking cars in two separate points. I think it’s easiest to turn around and do the climb in the reverse direction – which feels much more comfortable on the way back. No matter where you are on this hike, you’ll encounter views of the Ko‘olau Mountains, turquoise waters and white sand of the windward bays and beaches.
Commonly known as Crouching Lion for the rock formation that hovers above the quaint town of Ka‘a‘awa, this pu‘u, or cliff, might be the toughest to summit on O‘ahu. With sheer cliffs on either side of the trail throughout the 4-mile loop, Crouching Lion is reserved for seasoned hikers. The entire trek back into the foliage takes roughly 4-5 hours, depending on ability and trail conditions. Despite the risks involved, Pu‘u Manamana’s vistas of Kaneohe Bay, Kahana Bay and Laie are unmatched. And once again, pictures on the precipice are sure to please on social media, if you’re into that. But there are no illusions here; every mile and cliff is earned on Crouching Lion. Also of note, the trail ends next to an old cemetery, adding to the eeriness apparent throughout this hike. The legend, as told by Hawaii Magazine, is that the lion demigod Kauahi was sent from Tahiti to keep watch over Kahana Valley and Ka‘a‘awa Village.
“Ka‘ala is ca‘allin’ my name,” my best friend and hiking partner used to say when she was craving a climb up O‘ahu’s tallest peak. With a 4,025-foot summit and 10 strenuous miles of hiking involved, Mt. Ka‘ala requires commitment and planning. I only completed Ka‘ala once, and it took us roughly 8 hours with a stop for lunch at the top near the “golf ball” telecom structures that can be seen from most places on the Island. There are several ways to access the trail in the Wai‘anae Mountain Range, also known as the Dupont Trail. We began on the west side at the end of Wai‘anae Valley Road, climbed up the gnarly, muddy ridge filled with ropes and diverse botanicals and traversed down the North Shore-facing edge toward Waialua High School. Note: to enter this way is nearly impossible, as it’s on private property, permission is required and rarely granted anymore. As the tallest peak on the Island, Mt. Ka‘ala comes with the ultimate bragging rights – and views, if they are not blocked by thick fog at the peak.