Kaiwa Ridge (Pillbox) Trail

MODERATE 848 reviews
#2 of 3 trails in

Kaiwa Ridge (Pillbox) Trail is a 5.1 kilometer moderately trafficked out and back trail located near Kailua, Hawaii that features beautiful wild flowers and is rated as moderate. The trail is primarily used for hiking, walking, and trail running and is accessible year-round. Dogs are also able to use this trail but must be kept on leash.

DISTANCE
5.1 km
ELEVATION GAIN
380 m
ROUTE TYPE
Out & Back

dogs on leash

hiking

trail running

walking

views

wild flowers

wildlife

muddy

rocky

scramble

Great short rocky steep hike along the Ka'iwa Ridge offers great views of Lanikai and Kailua. Near Waimanalo Beach - wonderful white sand and calm water, Lanikai and Kailua Beaches The Kaiwa Ridge Hike is great to go either sunrise or late afternoon short 0.6 mile each way but gains 500 ft so is steep in places with great views along the way - It takes about 30 minutes or less to hike from the trailhead to the top (second) pillbox (elev. 565-ft). Its another 10 minutes to reach the ridge's highest point (elev. 603-ft) marked by a geodetic marker (the small concrete platform with broken surveyor's pole). The "official" trailhead, unmarked, is about 40 feet uphill on a paved, private driveway along Kaelepulu Drive. The driveway is opposite of the Mid Pacific Country Club & Golf Course just before you reach an exclusive, gated community. The first part of the trail is very steep, slippery, and can be confusing. This trail is undeveloped. The trail is rocky, windy and rewards you with a great view on top of the pillboxes. No guardrails so can be dangerous for young children. Also the trail is very poplular and can be crowded.

1 day ago

They probably went via Poopoo Place or Kamahele St., the two alternate backways.

hiking
1 day ago

This trail is CLOSED for now. Not sure how others can review it in the past weeks. They have signs posted.

I’m going on my past experience before it was shut. Great views and awesome for exercise.

6 days ago

What a breathtaking view up there definitely must do trail

hiking
13 days ago

Caught the sunrise. Super crowded but worth it.

17 days ago

Unfortunately the trail is closed for the next couple months and there's a guard

hiking
17 days ago

Need a little fitness to get up to the pillboxes but wow, what a view .. we were blessed with clear sunny skies and waters to blue.

hiking
20 days ago

Closed currently for renovations but great hike to watch the sunrise. Be sure to check the weather and make sure it didn’t rain recently otherwise you’ll be walking through mud. The trail is busy all day long.

22 days ago

While the trail is temporarily closed it is such a beautiful one. The hike up is nothing too special but the views are wonderful. A great sunrise location!

hiking
23 days ago

Due to the volume of tourists there are safety concerns. They are making repairs and improvements. I live in Kailua, it’s a great little trail. it’s not easy and you need good shoes. Once you’re up there the views of Lanikai are beautiful

hiking
25 days ago

This trail has been CLOSED! Please add this to the title of this trail as we got up at 4AM and didn’t read all of the comments below.

Guard was not friendly and the road is now private.

hiking
28 days ago

I went pre- closure last year and it was a struggle if you didn't have the right footwear! Very slippery and steep at the beginning and end. Saw lots of people fall including myself! Loads of rubble! The top view from the pillboxes were worth it!

1 month ago

Lots of hikers walking to the trail, lots of hikers turned away by the guard.

1 month ago

Gorgeous views of Lanikai Beach from the top- a fairly easy hike with lots of people.

1 month ago

Talked to the guard - closed for the next 2-3 months

trail running
1 month ago

It sure looked neat but there was a guard turning people away today (7/7/18).

1 month ago

The trail is closed for renovation. Police are posted to keep you out. July 7 2018

hiking
1 month ago

This is simply a great hike. I have only entered from the one entrance on Kaelepulu Drive across from the Country Club and Golf course. Right before a gated community. This is a tough part of the hike. Steep (there are some old ropes if you need them) and can be very slippery especially after a rain. For my wife and I this was fairly easy, but had to use some caution with my 9 and 6 year old but they made it up this initial point no problem. The views are stunning. Some of the best photos we have taken and gives you a better understanding of why everyone loves Hawaii. The one thing I didn't like was the dogs. They have to be leashed, but people don't listen and let them off. I am currently not a dog owner, but what I have noticed is that people don't want your kids to come up to their dogs without permission. However they will allow their dogs to come up to you or your kinds without your permission. It really bothers me. Make sure you bring water, because there is no cover and it gets hot. Great hike, I plan on going back with just myself and the wife and really stepping it out. Should be a great workout.

1 month ago

There is another non-descript entrance via Kamahele St. It takes you up from the back side.

1 month ago

Went to the trail on June 28 and it is closed for repairs with No trespassing signs all over. There is also no parking here.

hiking
1 month ago

Closed for Two Months for repairs starting June 21. Very eroded. Fenced off on the Kaelepupu entrance and a fence runs up the trail to the first landing.Haven't looked at the Poopoo pl entrance. Don't tresspass of the first fenced uphill sections is pretty dangerous, I saw some tourists bush wacking through people's backyards. If you really going to trespass whihc i don't recommend, it's probably safer to just hop the fence.

hiking
1 month ago

Hiked the whole thing this morning. Started at the pillbox side and popped out in a Lanikai neighborhood. Pretty much had the whole trail past the pillboxes to myself. The path gets narrow but was easy to follow.

1 month ago

always an awesome hike. views for days. bring water and a good attitude

1 month ago

Very nice hike and so pretty for sunrise! Baby wore my 5 month old son! I'd definitely do this hike again

hiking
1 month ago

Enjoyed the hike. Definitely steep and you have to watch your footing going down, but the views are amazing. We went during the heat of the day so I would recommend going early to beat the heat.

1 month ago

Favorite hike on Oahu thus far, just a great combination of not being to long for my five year old yet still a challenge for myself. Awesome views from the pillbox.

hiking
1 month ago

Very steep. Beautiful but difficult getting down. Be sure to go when it’s dry.

hiking
2 months ago

Steep climb makes this a more difficult hike even though the trail is relatively short. Views from the pillboxes are absolutely gorgeous!

hiking
2 months ago

this is a favorite! a bit steep in the beginning but then very easy the rest of the way through. it's a very crowded hike though so be mindful of others! sunrise is my favorite time to hike it! make sure you also go on a dry day!

hiking
2 months ago

Nice hike with beautiful views. It's really not that hard. Once you made it to the first pillbox, the most challenging part is behind you. Most people turn around at the second pillbox, wich means the rest of the trail isn't really trafficed. Also, after the second pillbox, as the trail is less used, the trail get narrow and there are lots of catutuses along the way. Wearing long pants could be a good idea.Unfortunately, the highest point of the trail is coved by trees and bushes and doesn't really offer good views, but the trail in general is nice to hike.

2 months ago

did the entire 3+ miles..last 1.5 miles the trail was taken over by the vegetation..its there you just have to fight through the overgrown branches and watch your footing

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