Kaiwa Ridge (Pillbox) Trail

MODERATE 770 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.

trail running
4 minutes 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
2 days 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.

8 days ago

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

15 days 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
19 days 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.

20 days 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.

23 days ago

Maintenance has been postpone till further notice.

hiking
24 days 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!

25 days ago

Good sunrise, million people with speakers blaring though.

25 days ago

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

1 month ago

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

1 month ago

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

1 month ago

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

hiking
1 month ago

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

hiking
1 month 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
1 month ago

Great hike! Great views

hiking
1 month 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
1 month ago

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

hiking
1 month 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.

1 month 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.

1 month 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
2 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.

Awesome hike! It’s not difficult to hike!

hiking
2 months ago

Amazing sunrise views, a little steep at the beginning but otherwise a reasonable hike. Only took us about a half hour to get to the first and second Pillboxes. Would definitely do it again!!

hiking
2 months ago

Awesome hike. Started in the dark and saw a beautiful sunrise from the second pillbox. Very steep in spots, but would rate moderate. It did start raining on the way down which made it very challenging and slippery to get down. If you like a challenge and don’t mind getting a tad dirty this is your hike!

hiking
2 months ago

We parked few blocks away and walk to the entrance. Make sure your car is parked on the side of the road, wheels don’t touch the pavement. Great hike, I would rate it moderate. Easier than Olomana trail. Nice views, keep hiking pass the pillboxes. There were few families with the young kids. So it’s not very strenuous. Careful on the way down!

2 months ago

Very steep, slippery when wet. Stunning views!

hiking
2 months ago

Short, moderately steep hike with well-worth it views!! Beautiful!!

2 months ago

some challenging portions, great views. a solid intermediate level climb

2 months ago

You can actually hike all around the whole ridge. You can stay left and end up back in Lanikai beach or go right and end in the Kailua about a mile and a half from where pillbox started. I went left and love it. view just as good and almost no foot traffic

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