Here are my TOP 20 FAVORITE HIKES on Oahu (not in order). Not including my favorite... 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.
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.
- Tips: Wear sturdy shoes; the trail is short but steep. Not officially marked, so proceed cautiously.
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.)
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.
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.
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:
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.
Further Directions:
If Deadmans 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.
Deadman's Catwalk
Allison's Hidden Stairs
Hamama Falls
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.
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.
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.
Hamama Falls
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.
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.
Further Directions:
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.
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.
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.
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.
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.
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.
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.
Honorable Mentions:
Hanauma Bay Trail
Koko Crater
Mount Olympus
Olomana Three Peaks
Manoa Falls
Upper Manoa Falls
The Judd Trail
The Cabin
Secret Waianae Sunset Spot