Best Hikes on Oahu & More: Top 20

The Best hikes on Oahu are subjective, but here are my TOP 20 FAVORITE HIKES on Oahu (not in order). Not including… The Stairway to Heaven. Honorable mentions are at the bottom of this page.

HIKE AT YOUR OWN RISK. @sidequestcoop is not responsible for any injuries, fines, or violations you may incur. This website is solely to showcase the beauty that nature has to offer on the island of Hawaii and help you find something to do!

Crouching Lion Mini Hike

Location: Kaaawa, Hawaii

Distance: ~0.5 miles round trip
Difficulty: Moderate to Hard (steep and slippery sections)
Highlights: Stunning coastal views of Kahana Bay and lush greenery.
Directions: Park near Kahana Bay. Trailhead begins along the side of the road; look for a faint path heading upward. MAKE SURE YOU TAKE THE PATH ON THE LEFT. (this is the easiest one)
Tips: Wear sturdy shoes; the trail is short but steep. Not officially marked, so proceed cautiously.

Further Directions:

Service over here is bad. Make sure you park by Kahana Bay and do not leave any valuables in your car. I have seen broken glass here multiple times. Signs here will tell you that as well.

Make sure to go on a sunny day for the most scenic views. (This hike will end when you want it to.)

Personal Story: For a regular hiker, this is easy. For someone who has never hiked before… this might be intense. I took my borther on this hike and he stopped because he was genuinely scared for his life. Then my one friend from out of town stopped in the exact same spot as my brother because of the same reason. You will see a grave site here in honor of an HPU soccer player who fell off the edge. This story is very sad, remember no picture is worth your safety.

Sacred Falls (Note: Closed to the public due to safety concerns)

Location: Hauula, Hawaii

Distance: ~4 miles round trip (if accessed illegally)
Difficulty: Moderate (flat but slippery)
Highlights: Gorgeous waterfall nestled in a secluded valley.
Directions: Not advised due to fines and risks. Consider alternative waterfalls like Lulumahu or Hamama Falls. Very easy to get lost as the trail is very overgrown and you mostly make your own way along the stream.
Tips: Respect closures to avoid legal trouble and hazards.

Further Directions:

Cops will issue tickets to those who trespass. There is another trail to the left of this gate in front of the beach.

Personal Story: This hike is the creepiest hike on Oahu. I had to hide in the woods when two random dogs appeared out of nowhere, and they were running in sync. It actually looked like robot dogs. My roommate was begging me to turn around. On the way back, we did get lost after following what we thought was the same path. Something about this place is extremely eerie. This place is closed indefinitely because of the incident that happened on Mother’s Day 1999. 50 people were injured, and 8 people died. Always bring an offering here.

Lanikai Pillbox Hike

Location: Kailua, Hawaii

Distance: ~1.8 miles round trip
Difficulty: Moderate
Highlights: Iconic sunrise views of the Mokulua Islands, WWII-era bunkers.
Directions: Park near Lanikai Beach or on Alapapa Dr. Trailhead is on Kaelepulu Drive by Mid Pacific country club. The beginning of the trail is the steepest part. (This can be quick if you want it to. Jordan and I made it to the pillbox in 10 minutes one time lol.)
Tips: Best done at sunrise or early morning to avoid crowds and heat.

Personal Story: I have been on this hike countless times, and every time it is truly breathtaking, but certain times are better than others. For example, this area is extremely busy and nearly impossible to find a parking spot once the sun is up because of tourism. Go at sunrise for the best experience. I think this hike is easy, my record time is 10 minutes… but for some people it is extremely hard. My dad did it twice and almost passed out at the same spot.

Pink Pillbox (Pu’u O Hulu)

Location: Maili, Hawaii (Near Waianae)

Distance: ~2 miles round trip
Difficulty: Moderate
Highlights: Vibrant pink pillbox, panoramic views of the Waianae coast.
Directions: Trailhead starts at Kaukama Road in Maili.
Tips: Late afternoon offers beautiful lighting; bring water and sunscreen.

Further Directions:

This is the start of the trailhead that goes all the way up. Park nearby and make sure to leave no valuables in your car. Car break-ins do happen here.

Personal Story: This area is not very welcoming to tourists, and every time I see broken glass where people park from break-ins. Try to only go during broad daylight. If you go for sunset, it will be amazing, but when you come back down, your windows might be broken. The sad truth is that tourists are targeted… especially rental cars because they know it most likely does not affect you.

Deadman’s Catwalk (Kamehame Ridge) & Allisons Hidden Stairs

Location: Honolulu, Hawaii

Distance: ~2 miles round trip
Difficulty: Moderate
Highlights: Spectacular views of the windward coast; remnants of the old “catwalk.”
Directions: Trail begins in Hawaii Kai near the Kamehame Ridge neighborhood. Entry may be restricted. The directions to get to the right location are: 1336 Kamehame Dr. Honolulu, HI 96825
Tips: Respect local residents and any restrictions.

If Deadman’s catwalk is on the right… Allison’s hidden stairs are on the left. They are hidden, but they are nearby. Keep following the subtle stairs until these yellow stairs appear out of nowhere.

Personal Story: The start of this hike, you will see that you are crossing boundaries, going onto private land so it does come with risks. Every time I have been on this I have seen someone walking their dog or families enjoying the view, so you are most likely ok. In my opinion this is one of the safest hikes on island because it is almost entirely a paved path.

Ehukai Pillbox (Sunset Pillbox)

Location: Pupukea, Hawaii

Distance: ~2 miles round trip
Difficulty: Moderate
Highlights: Views of the North Shore, Sunset Beach, and turquoise waters.
Directions: Trailhead near Sunset Elementary School. Park at the park connected to Sunset Beach Elementary. This is right across from pipeline beach. You will see the trailhead that will take you up to these pillboxes. The trail is very wide open and clear.
Tips: Ideal during sunset for breathtaking views.

Personal Story: Ehukai Pillboxes is personally my favorite pillbox hike on Oahu. The North Shore is just completely my scene, and it is a shorter, laid-back hike. Because of social media it has gotten extremely popular around sunsets, but it is completely worth it. At most times during the day… on a weekday, you might be the only person up here.

Hamama Falls

Location: Kaneohe, Hawaii

Distance: ~4 miles round trip
Difficulty: Easy to Moderate
Highlights: A serene waterfall and a peaceful forested trail.
Directions: Located in Kaneohe; trailhead begins at Waihee Road.
Tips: Respect private property near the trail entrance.

Personal Story: This hike is actually not easy to locate at all. It is a hidden waterfall that used to have military ties. On the left side of the waterfall, there is a military door buried inside the mountain that used to be a storage for old munitions.

Kaena Point Pillbox

Location: Waialua, Hawaii (Near Makaha)

Distance: ~5 miles round trip
Difficulty: Moderate
Highlights: Pillbox, stunning secluded beach, and potential wildlife sightings (monk seals). The tide pools were my favorite because the water looked the most clear I have ever seen.
Directions: Located right near Makua Beach. The trail will take you all the way to the westernmost point of Oahu.
Tips: No shade—carry plenty of water and wear a hat.

Personal Story: Yes, this hike is a straight path… but do not underestimate it. During the day, this like is lethally hot. The west side sun is no joke. I recommend going early morning to avoid the rays and the traffic the beaches may draw. This is a sacred site as well and I did find this journey to be a little eerie.

Lulumahu Falls

Location: Honolulu, Hawaii

Distance: ~2 miles round trip
Difficulty: Moderate
Highlights: Hidden waterfall surrounded by lush vegetation.
Directions: Trailhead starts near Pali Highway. Follow signs carefully.
Tips: Can be muddy; waterproof shoes recommended.

Located right off the Pali highway heading toward Kaneohe. This is the busiest hike on the island in my opinion. There is also the most parking. I suggest going very early to beat the crowd. Avoid going before sunset as I hear stories of hikers getting lost over here.

Personal Story: Extremely populated… cool views and an easy hike, but it is really annoying when there is 300 people at a waterfall like what…

Pali Notches

Location: Nu’uanu Valley (Honolulu County, Hawaii)

Distance: ~0.8 miles round trip
Difficulty: Hard (steep and exposed sections)
Highlights: Ridge views of the windward side, thrilling ridge trail.
Directions: Park at Pali Lookout. Trail begins at the edge of the parking lot.
Tips: Only for experienced hikers; avoid during high winds or rain.

Personal Story: This hike is actually sketchy at a certain point. I was too scared to go all the way to the top when I saw a helicopter rescue X, and it was very narrow. I hear stories of people getting saved and fined here all the time.

Pali Puka

Location: Nu’uanu Valley (Honolulu County, Hawaii)

Distance: ~0.8 miles round trip
Difficulty: Moderate to Hard (steep ascent)
Highlights: “Puka” (hole) in the ridge with panoramic views.
Directions: Starts at Pali Lookout. THIS IS ALL THE WAY ON THE LEFT SIDE BY THE PORTABLE BATHROOMS.
Tips: Wear sturdy shoes; trail is steep and narrow.

Personal Story: The Pali Puka hike is a sacred and forbidden hike I did not know till after. This hike is extremely eerie. Something that happened recently is a man tried to push his wife off the edge, and she escaped… yeah, insane. The wind is strong in this area and it rains often so if you do, make sure you are in the clear.

Pali Twin Falls

Location: Nu’uanu Valley (Honolulu County, Hawaii)

Distance: ~1.5 miles round trip
Difficulty: Moderate
Highlights: Two picturesque waterfalls and a peaceful forest.
Directions: This is directly at the Pali lookout. There is a gate on the right that has a spot you can slip through. Sometimes the gate will just open with a pull. Take the path down until you see a clearing and an incredible view of Kaneohe on the left. On the right, there is a stream and a subtle trail you will follow all the way down to the falls.
Tips: Slippery sections—use caution after rain. MAKE SURE TO GO AFTER RAINFALL. I have been here multiple times and it has been dry.

Personal Story: The Pali Twin Falls hike is past the locked gate at the Pali Lookout. It is blocked because boulders fall off the mountains and it is an extreme liability. This is a hike to only do when it is raining heavy or it will be dry.

Upper Makua Cave

Location: Waialua, Hawaii (Near Makaha)

Distance: ~0.8 miles round trip
Difficulty: Moderate
Highlights: A large sea cave with panoramic views of the Waianae coast.
Directions: Park near Farrington Highway and right by the lower Makua cave. Trailhead is unmarked but you can located it by the no-trespassing signs. Head straight up through the long brush. Veer toward the left side as you will eventaully see markings that will let you know you are in the right direction. This is difficult to find. We did spend a lot of time looking in the wrong spot so remember go straight up, but VEER LEFT.
Tips: Bring a flashlight for exploring inside the cave.

Personal Story: Upper Makua Cave is actually a risky hike. First… your car has a risk of getting broken into. Second… you are technically going onto a military base, and that is not allowed. Third… it is hard to locate. The first time I did this hike it took me two hours to find the cave, believe it or not. The second time I did it, I found it in 30 minutes.

Waimano Falls

Location: Pearl City, Hawaii

Distance: ~3 miles round trip
Difficulty: Moderate to Hard (steep incline on return)
Highlights: A beautiful waterfall with a swimming hole.
Directions: Trailhead starts at the end of Komo Mai Drive in Pearl City. This is at the top of a neighborhood and parking is limited. A marked trail will take you down to this jumpers oasis.
Tips: Bring bug spray and water; trail can be muddy.

Personal Story: This hike is cool but I would probably never to it again because I am scared of leptospirosis.

Naniuapo Falls

Location: Honolulu, Hawaii

Distance: ~3 miles round trip
Difficulty: Moderate
Highlights: Tranquil waterfall tucked away in lush forest.
Directions: Located in Kaneohe; trail begins near Wai’aloa way and Haukulu Road. This trail is gated off so complete at your own risk. Take the initial trail on the left. Be on the lookout for markings on the trees to let you know you are going the correct way. Once you find the falls and mysterious military equipment located near it, heading back you will see there are trails that go straight upward on the right side. There are some ropes to help your adventure go smoother. Up here we did see wild pigs and an incredible ridge view.
Tips: Best visited after light rain for optimal flow.

Personal Story: I was with a friend, and when we were trying to find this waterfall, we came across three barefoot and shirtless people in the woods. Our hearts dropped because we thought we were going to get attacked, but they ended up just being regular people lol.