It’s hard to come up with a list of the best hikes in Oahu, because there are so many good ones!

Even though it’s the busiest and most populated island in Hawaii, Oahu still has some great nature trails to get away from the bustle and see some spectacular mountains, beaches, and waterfalls.

A few of these trails are difficult or technical, but there are also lots of easy hikes on Oahu for the families and older folks, including some near the Honolulu area that you can reach a short distance from the city.

1. Stairway To Heaven (Haiku Stairs)

This Oahu hike is epic, scary, and slightly illegal. Still interested? The ‘Stairway to Heaven‘ takes you to the top of the Ko’olau mountains via 3,922 metal stairs of pure adrenaline. At some points, the stairway is almost vertical, clinging to the side of the steep mountain.

There’s an old World War II radio station at the top of the mountain, but the stairway has been closed since the 1980s, and fines of up to $1,000 have been given out to people caught climbing it. The area is even patrolled by security guards around the clock.

Still, thousands of people make the climb every year, and for good reason — it’s one of the most spectacular hikes on Earth!

I first discovered this hike on the internet in 2015 and knew I had to try it. Not only are the views out of this world, but the whole experience is just beyond awesome and unique.

Even after traveling in many countries now, this is still probably my favorite hike in the world. It may never be topped!

Distance: 2.3 miles (3.7 km) roundtrip
Elevation Gain: 2,625 feet (800 m)
Difficulty: Hard

2. Moanalua Valley Trail

If you want to see the ‘Stairway To Heaven’ legally, with virtually no chance of fines, you can hike up the Moanalua Valley Trail on the back side of the same mountain. This is known as the back way for the Stairway To Heaven.

Keep in mind, to stay 100% legal on this hike you will have to go back the same way you came. If you hike up the Moanalua trail and then down the stairs, you’re still risking a fine, because the stairway is not legal.

However, it’s possible to take some great pictures on the stairs and then leave via Moanalua without hiking the entire stairway from top to bottom, that way you get to experience two epic hikes in one.

The Moanalua trail can be muddy after rain, so check the conditions before you go. You definitely want good weather for this hike. Wind and rain can make it much harder and more risky.

Ironically, the general consensus is that the stairs are actually a safer and easier route to the top of the mountain. The main reason to take the back way is to stay legal and rule out any possible fines.

Distance: 9 miles (14.5 km) roundtrip
Elevation Gain: 2,800 feet (850 m)
Difficulty: Hard

3. Crouching Lion Hike

Crouching Lion is one of my favorite Oahu hikes. It’s a short but epic trail that ends with a panoramic view of the mountains and jungle at Kahana Bay, in northeast Oahu.

You can stop at this hill after an easy hike, or keep going up the mountain and the trail will eventually merge with Pu’u Manamana, one of the scariest and most dangerous cliff trails in Hawaii.

All in all, Crouching Lion is definitely one of the best hikes in Oahu!

Distance: 0.5 miles (0.8 km) roundtrip
Elevation Gain: 300 feet (90 m)
Difficulty: Easy / Moderate

Crouching Lion Hike — one of the best hikes Oahu has to offer!

 4. Lanikai Pillbox Hike

The Lanikai pillbox is one of the easiest Oahu hikes and also one of the most popular spots on the windward side of the island.

This hike takes you to a couple of World War II-era concrete bunkers above Lanikai Beach, and the 360 degree views that you get on top of the bunkers are amazing.

It’s a very short hike (you could probably do it in 15 minutes if you rushed), but it’s all uphill and a bit strenuous, so it still feels plenty challenging.

Last, but not least, the Lanikai pillbox is one of the best sunrise and sunset spots on the whole island!

Distance: 1 mile (1.6 km) roundtrip
Elevation Gain: 450 feet (140 m)
Difficulty: Easy

Lanikai Pillbox Hike

Lanikai pillbox at sunrise — one of my favorites!

5. Ho’omaluhia Botanical Garden

This one’s not really much of a hike per se, but it’s more like an easy stroll on a path around a lake.

Even so, it’s one of the most stunning places on the island of Oahu, and it’s free to visit, so you can’t miss it. This hike is a great one for families or older folks.

The Ho’omaluhia Botanical Garden has more than 400 acres of Jurassic Park-esque tropical scenery, making it perfect for a morning walk or jog. The lake has stunning reflections if you go in the early morning.

Distance: 1 mile (1.6 km) roundtrip
Elevation Gain: 100 feet (30 m)
Difficulty: Easy

6. Chinaman’s Hat (Mokolii Island)

The Chinaman’s Hat island, also called Mokolii island, is a neat little mini island that got its name from the unique shape that looks kind of like a traditional Asian rice farming hat.

This is a little island located on the windward side of Oahu, and the best way to reach it is by kayak, or sometimes it’s also possible to wade to it when the tide is low.

You may not see this one very often on lists of the best Oahu hiking trails, but the climb to the top of the ‘hat’ is a good, rocky scramble and you’re rewarded with some amazing views of the Ko’olau mountain range!

Distance: N/A
Elevation Gain: 200 feet (60 m)
Difficulty: Moderate

Read More: Chinamans Hat Hike

Kayak Chinamans Hat island and bring a drone to capture views like this!

7. Diamond Head Lookout

The Diamond Head hike is a paved trail with railings most of the way, taking you to the top of the old Diamond Head volcano crater.

From the top, you can look out over Waikiki and the whole Honolulu cityscape, and you also get to see the remains of some World War II pillboxes.

This trail can be pretty busy with tourists sometimes, but I still think it’s worthwhile for the city views from the summit.

Distance: 1.8 miles (2.9 km) roundtrip
Elevation Gain: 500 feet (150 m)
Difficulty: Easy

Read More: Diamond Head Crater Hike

8. Pink Pillbox Hike

The Maili pink pillbox hike is another ridge hike that takes you to some small World War II bunkers on the west side of Oahu, including a pink painted bunker at the top of the ridge.

This hike is starting to become popular, but it’s still not as crowded as some other trails like Diamond Head or the Lanikai pillboxes!

It has awesome views of the nearby beaches, highway, and suburbs from above.

Maili / Pink Pillbox hike

The graffiti covered pillboxes have amazing views of the coastline and ocean at Waianae. There are slit windows inside the bunkers, so you can look out of them while hiding from the sun for a bit!

Distance: 1.2 miles (2 km) roundtrip
Elevation Gain: 500 feet (150 m)
Difficulty: Easy

Read More: Pink Pillbox Hike

Amazing views of the Waianae coast at the Maili pink pillbox hike

9. Ka’ena Point Trail

The Ka’ena Point hike takes you to the remote western tip of Oahu island. You can do this hike from two different starting locations (Waianae or North Shore), and both are nice.

Ka’ena Point is a pretty quiet part of the island and it’s also a wildlife sanctuary, so it’s a great place to see Hawaiian monk seals, humpback whales, and other animals!

In one hike, I counted half a dozen monk seals lounging on the rocks at Ka’ena Point.

Ka’ena Point Hike

It’s a 5-6 mile roundtrip hike to Ka’ena Point, but the trail is flat all the way, making it pretty easy overall.

This is one of the more family friendly hikes on Oahu and it’s great for kids, although I’d try to avoid the midday heat. This is also one of the best sunset spots on the whole island.

Keep in mind if you do Ka’ena Point for sunset then you’ll be walking back to your car in the dark, so it’s a good idea to bring a headlight.

Also, if you do the hike from the southwest trailhead (Waianae), you have to park outside of the gates, because they lock these at 7 PM, and you don’t want your car to get locked in for the night. We had that happen once!

Distance: 5.5 miles (9 km) roundtrip
Elevation Gain: Minimal
Difficulty: Easy / Moderate

Read More: Kaena Point Trail

Hawaiian monk seal lounging on the beach at Kaena Point trail

Sunset at Ka’ena Point

10. Upper Makua Cave

The short but steep hike to Upper Makua Cave is not recommended if you have a fear of heights. This one is a guaranteed adrenaline rush.

It’s a hidden gem on the west side of the island, and there were only a couple of other people on the trail when I went.

The view from inside the cave looks like a picture frame of the west coast! It’s a very unique view.

Distance: 0.6 miles (1 km) roundtrip
Elevation Gain: 425 feet (130 m)
Difficulty: Easy

 
 11. Hanauma Bay Ridge Trail

This is a short, paved hike that gives you sweeping views of the beautiful Hanauma Bay, which is one of Oahu’s most famous snorkeling spots. The hike can be as long (or short) as you make it.

Most people will only follow this trail to the top of the ridge and then turn around, but if you continue south along the bay you can find a natural rock bridge by the sea and other interesting sights.

Morning is the best time to do the Hanauma Bay Ridge Trail since it’s better for photos and not quite so hot. The trail starts from a locked gate right by the entrance to Hanauma Bay.

Distance: 1.5 miles (2.4 km) roundtrip
Elevation Gain: 500 feet (150 m)
Difficulty: Easy

Hanauma Bay Ridge Trail — one of the top hiking trails in Oahu.

12. Mauna Lahilahi

Mauna Lahilahi is a small, rocky mountain on the Makaha coast, with beautiful beaches on both sides.

This hike is a bit of a hidden gem on the west side of Oahu. You can reach the top in only 15 minutes, but it requires some short rock scrambling that could be unnerving for inexperienced hikers. Proceed with caution.

At the top, you get amazing 360 degree views of the Makaha coastline, with Papaoneone Beach and the Hawaiian Princess Resort dominating the landscape.

Distance: 0.5 miles (0.8 km) roundtrip
Elevation Gain: 200 feet (60 m)
Difficulty: Easy / Moderate

Mauna Lahilahi panorama

13. Koko Head Stairs

The Koko Head hike is like Hawaii’s version of the famously challenging Manitou Incline in Colorado. The hike to the top of this old volcano crater is a huge workout, hence the nickname ‘Stairs of Doom.’

The elevation on this hike isn’t as bad as the Manitou Incline, but Hawaii’s midday heat and humidity can still make it pretty tough. It’s not a dangerous hike and there haven’t been any falling deaths, but it’s a real fitness test and may not be fun for everyone.

I’ve hiked the Koko Crater trail many times over the years, and it’s always great fun. I hated this hike the first time I did it, but now I’ve really grown to enjoy it. It easily belongs on a list of the best hikes in Oahu!

The good news is that this is also one of the best places to watch the sunset or sunrise on the whole island of Oahu. I’ve climbed Koko Head almost a dozen times now for sunset, and the view at the top is always spectacular.

Distance: 1.6 miles (2.6 km) roundtrip
Elevation Gain: 900 feet (275 m)