Kaiwa Ridge (Pillbox) Trail

MODERATE 796 reviews
#1 of 3 trails in

Kaiwa Ridge (Pillbox) Trail is a 3.2 mile 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
3.2 miles
ELEVATION GAIN
1246 feet
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.

4 days 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

great views, nice trail

8 days ago

Good easy hike. Great at sunrise

14 days ago

My husband and I took our dog today and we had a blast

18 days ago

Steep climb up but so many spots along the way to stop to enjoy the view(and rest). Gorgeous view and not over crowded like diamond head.

22 days ago

good fast climb, short, great views very slippery when raining... it's doable though my 10 year old daughter did it when it was pouring.

hiking
25 days ago

I’ve done “the pillbox hike” numerous times over the last three years. Leading up to the pillboxes is pretty steep and slick when wet. It’s always fairly crowded due to the amazing views. Sunrise is unbeatable! Get there early for a good spot. Today was the first time I kept going to the end of the trail. The panoramic views are hard to beat! The trek down was an adventure. Slipped a few times and there are hidden rocks on the trail that are tough to see. Overall, highly recommend it! If you do the full hike, take your time on the second half and watch your footing.

hiking
28 days ago

Great hike! Would say moderate to hard especially coming down as it was very steep and loose mud was slippery. Wear hiking/ trail shoes if you have them! Views were amazing and this was a really nice short hike

trail running
1 month ago

Fun trail to run. It can be pretty crowded and parking can be hard to find due to the proximity of the beach. The trail itself has multiple ways to the top so every time can be different. A few small places to rock climb. At the top there is a beautiful view of the beach and at sunrise it’s indescribable!

hiking
1 month ago

I do this hike weekly. Nice and easy a lot of people usually stop at the pillboxes but the hike continues on I say stop enjoy the view get pictures and then continue on.

1 month ago

Amazingly beautiful hike! Completely doable with small children! Super muddy and slippery after or during rain.

1 month ago

Pretty steep at beginning and the end (out n back trail). But fun hike. Almost got hit with someone’s drone tho. So that sucked. But I weaved and dodged like a bobcat

hiking
1 month ago

Did this one about a month ago. Pretty good hike, even better views. If you can climb up on top of the pillboxes, you get a nice view all around. A little steep and tricky coming down, not too bad though. Definitely one of my favorites during my visit.

1 month ago

Beautiful views of Kailua but you should probably be prepared to go uphill a lot and it can be slippery so be careful. I really loved this hike because the views are gorgeous but it is a very popular hike, and with that comes a lot of people. So if you are wanting to get away from it all, this is not the right hike for you.

1 month ago

Maintenance has been postpone till further notice.

hiking
1 month ago

3/30/18-Started about 0715 and came across 23 groups/solo hikers. (Read in the news yesterday that the maintenance work was postponed.) Actually found a relatively close parking spot near the trail head but there were signs posted warning that all street parking is closed from 3/30 - 4/1 from 1000 to 1500 or 1700 (I can’t recall which). The trail was dry and the view was nice from the top!

1 month ago

Good sunrise, million people with speakers blaring though.

1 month ago

The trail will be closed for 60 days starting today for maintenance.

2 months ago

Short should wear good shoes little bit of effort. View was beautiful.

2 months ago

Very easy and fast hike... there was no parking near it though, all the old parking is now blocked off

2 months ago

We started on Kamahele and hiked through, then looped back to our starting point via residential streets. Great hike!

hiking
2 months ago

Breathtaking view at the pillboxes. Very steep and slick and I was really scared, but it was totally worth it.

hiking
2 months ago

Starts off steep and muddy but doesn’t stay that way for long. It becomes easy as you hike along the ridgeline of these grassy trails, with amazing views of the East shoreline and acres of blowing tall grass. There are 2 pillboxes, both easy to climb on top of.

THIS IS NOT THE PINK PILLBOX HIKE. Maybe no one else had trouble with this but when we searched “pink pillbox” into google maps with limited internet connectivity, they gave us this one. We spent quite a while searching for the third pink pillbox, not realizing until a day later that the pink pillbox hike is on the west side. Oops.

Second tip: don’t follow google maps’ suggestion of hiking a loop instead of heading to the highest peak and back. If you follow the trail all the way into the neighborhood, like we did, you’ll be met with a high private property gate and no way to get back unless you re-hike the mountain or call an Uber.

hiking
2 months ago

Great hike! Great views

hiking
2 months ago

Quick, easy (but steep) hike with great views the entire time. Wear sunscreen, bring water, and be prepared to share the trail with lots of new friends.

I know a few people have mentioned this isn't a good hike for kids, but I disagree. If your kiddos are used to hiking, they'll be completely fine. If a tourist can make it up in jeans and platform flip flops, your determined five year old can, too.

hiking
2 months ago

Paved the entire way and amazing panoramic views the length of the trail and especially at the end.

hiking
2 months ago

One of the most rewarding hikes. Stunning views throughout the trail. It is very steep at certain areas so I would say moderate, and street parking is annoying/scarce, but definitely worth going. I would not bring children unless they are older.

2 months ago

Not difficult to climb. Difficult to find a parking spot but the top had a great view. I would do this again for sure.

2 months ago

Loved this trail! It was a great work out! The views were amazing as well. I’m out of shape so found it to be a little difficult but would def do it again.

hiking
3 months ago

parking was difficult due tonroad closures and there were a ton of tourists that stand in the way of getting on top of the pillbox.

However the trail was gorgeous, and view was worth it on the top.

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