Top 7 hikes – Oahu

Having lived on Oahu for over three years, and being an avid hiker with my pups, I am sharing SEVERN of my favorite hikes on the island! Why seven? Well I was going to do 5, and just couldn’t leave any of these out! There are so many incredible hikes to choose from, so this felt nearly impossible when I started brainstorming. A few of these hikes I did almost weekly, while hikes like Stairway to Heaven were more of a “once in a lifetime” opportunity.

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Below are snapshot descriptions of each hike – if you choose to hike any of these, definitely look into All Trails for further information on exactly where to access the trailheads, as well as to review aerial maps of the hike. Travelers come to Hawaii and get lost hiking constantly, be smart, be safe, bring your cell phone and water, and tell someone where you are going. I know that might seem obvious, but it would surprise you how often these rules go unfollowed and hikers get lost.

Stairway to Heaven

Here it is – the once in a lifetime hike. If you’re lucky, you’ll do this more than once, but with the strict laws against hiking Stairway to Heaven, coupled with it’s constant state of deterioration, this will likely be a one and done hike for you. This is an EARLY MORNING hike, I mean like, 3am-4am start time. You will want to get to the entrance before the gate guard get’s there around 5am. You will also want to hike to the top before the sun rises for obvious reasons! My best advice if you want to check this hike off your Hawaii bucket-list is to check the latest news on the climb online, as the laws and condition of the trail change often!

Overall, plan for it to take several hours in complete darkness just to reach the top (bring a headlamp). The hike itself is entirely vertical on metal stairs, if you have a fear of heights this one really isn’t for you. Plan for it to be completely covered in clouds (therefore wet and cold) when you get to the top while waiting for the sun to rise, so pack a change of clothes to keep you dry and warm (just trust me on this). This hike is well worth the reward, the views of Kailua/Kaneohe and the mountain ranges are second to none. After you get back to your car, head on over to Cinnamons for some red velvet pancakes, or Kono’s for a Kalua pork burrito!!

Olomana (Three Peaks)

Warning – challenging hike ahead! Olomana (aka ‘three peaks’) is a physically demanding and technically challenging hike. It is located in Kailua on the Windward side of Oahu, and the trail is about 7k with 530 meters of elevation gain. Peak one is physically demanding but not ‘technically’ challenging, as with peak two, but peak three is another story. You can see the third peak in the photos above, and you are teetering on a very narrow ridge line during the entire climb. Without fail climbers fall to their death on this climb every year, so be safe and climb with other trusted climbers. If you feel comfortable, go for it! The views are absolutely worth the effort (look at those mountains in the background, jaw-droopingly beautiful). If you want some of the reward but aren’t comfortable with the last peak, just hike to peaks 1 or 2 and you can still enjoy the view! I highly recommend going on a non-rainy day, and definitely not after heavy rains, as with any other Windward side hiking trail.

Kuliouou Ridge Trail

It was purely bad luck that every time I photographed this hike there was dense cloud cover at the top, but I promise this hike is one for the books! Located south of Honolulu and not to be confused with Kuliouou Ridge Loop Trail, this climb is about 6.4 km with 495 meters in elevation gain, making for a tough workout to get to the summit. The trail itself is stunning and diverse, as you will pass through dense rainforest and then find yourself in a wide open pine tree forest. I always take my pups on this one because while it is long and physically demanding, there are very few narrow drop offs to worry about. If you want a hike on the South side of the island with beautiful views of Hawaii Kai and Honolulu from Ko’olau Ridge, this one is for you! It usually takes us about 3.5 hours round-trip, but you’ll definitely stumble upon runners absolutely crushing this trail!

Lanikai Pillbox

You will surely find this hike recommended by nearly all travel writers on Oahu, primarily because you get 5 star views with minimal effort. This hike is easily modifiable – meaning you can jaunt up to the first ‘pillbox’ in about 25 minutes and get the same stunning view of the Mokulua Islands and Lanikai Beach as someone who decides to spend upwards of 2 hours hiking all of the pillboxes and completing the loop. I have probably hiked this trail in every variation about three dozen times. The BEST time to go is before the sun rises, so that you can see that stunning sunrise over the Mokes, then make your way down for breakfast in Kailua, and park yourself at one of the most beautiful beaches in the world, Lanikai Beach. This hike is heavily trafficked, so get there early to get parking in the neighborhoods below, and take your spot on a pillbox to enjoy the sunrise.

Koko Head

AWESOME WORKOUT ALERT! Koko Head (Koko Crater Trail) is located on the South Side of Oahu in Hawaii Kai, a short drive from Diamond Head and Waikiki. It is the absolute best soul – crushing workout you can find on the island. As you can see above, this hike is a straight shot up 1000+ stairs to the top. This trail consists of abandoned railroad ties, leftover from when the military used them during World War II as part of an incline tram to transport supplies to a lookout post at the summit. Don’t let the lush photo mislead you, you will be in direct sunlight during the entire climb and it is HOT. Go early or go late in the afternoon, or be prepared to be hot hot hot. Like Lanikai Pillboxes, I have done this hike dozens of times, and used to time myself to see how fast I could get to the top.

PRO TIP: You can actually climb the back side of Koko Head as well! If you park by the Halona Blowhole and hop across the road and just start climbing up towards where Koko Head is, you can hike up a somewhat clearly trafficked area and get to the lookout at the top! After doing the stair side so many times, it can be a nice way to get the view from a different angle!

Lulumahu Falls

Everyone loves a good waterfall hike, am I right? Hawaii has no shortage of waterfalls, and the Pali Highway as well as Highway 3 (H-3) are the best places to catch dozens of waterfalls during or after rainfall, making it no surprise that one of the best waterfall hikes on Oahu is off the Pali Highway. This relatively easy but muddy trail is a must-do if you want to wade in the waters of a Hawaiian waterfall. The hike is about 3k with only 290 meters in elevation gain. The parking area is easy to find and the trail is well-marked, making it a great one for your kiddos and pups!

Kealia Trail

If you are looking to get away from the hustle and bustle of the city, or are looking to avoid highly trafficked hikes like Lanikai Pillboxes, Kealia Trail might be your best fit! This trail is located behind the Dillingham Airfield in Waialua on the North Shore of Oahu. You will actually park in the back at Dillingham Airfield to start your climb. This hike is especially enjoyable because it is a clearly marked hike complete with 19 switchbacks, and you will certainly see skydivers and glider planes soaring right next to you during the hike. This is another hike that you can make your own in terms of how far you want to go – I often took my dogs and hiked up all the switchbacks to the covered picnic benches and then ran back down (about 1.5 hours round trip), but you can pass the picnic benches and make this a 12.2 km hike across to the West Side of the island.