Kaiwa Ridge (Pillbox) Trail

MODERATE 839 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
1,246 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.

hiking
no shade
1 day ago

Gorgeous sunrise views!! Very crowded in the mornings so make sure you come EARLY to get parking if you want to see the sunrise. First lookout is maybe 15 min in and the dawn view is already good from there if you want to stop at that point and just chill.

hiking
3 days ago

It’s a great hike with great views! Be sure to take water because it can get very hot.
The hike can be done as an out and back or a loop by continuing past Pillbox #2 and hiking the ridge. The trail will dump you out on Luika Place. CAUTION!!! The trail gets really steep and narrow, the last 1000 feet or so. If it recently rained, forget about going as the trail will get slick and muddy.

Amazing view!

hiking
8 days ago

Steep quick hike with amazing views at the top. Cool WWII bunkers as well. Crowded and exposed so bring sunscreen and water.

10 days ago

The view is insane! The trail is not so hard but with the heat it could be rrally difficult for some. Bring a lot of water!

hiking
10 days ago

Awesome place to watch the sunrise. Pretty heavily trafficked at times but the views are worth it.

hiking
11 days ago

Quick, easy, and amazing views (especially for sunrise)! Recommend to anyone hiking in Hawaii. There are a couple parts that could be a little slick if wet, but just make sure you have decent shoes and this hike will be no problem.

hiking
13 days ago

This is a fantastically fun hike with a 360 degree view at the top. The trail is steep and a little bit of rock climbing is needed to get to the top, but still I think most hikers can reach the pillboxes no problem. This is a popular hike so the traffic was moderate along the trail.

13 days ago

Some spots are challenging but the view is absolutely worth it!

hiking
14 days ago

Always a beautiful hike, even on the 20th climb. Yesterday, we decided to hike the entire ridge, mostly out of necessity to evade the 100s of ill-equiped people at the pillboxes. The ridge is significantly less traveled which made it even more awesome. No drones. No music on speakers. No crying. The hike became 2000% better as we advanced beyond the pillboxes :)

14 days ago

Nice view to the beach and mountains!!

hiking
14 days ago

Amazing views of the ocean and unbelievable colors. Once you get past the second pillbox, you’ll have very little company on the trail. As others have noted, parking is impossible. I was dropped off, then walked back to the beach to meet my party. A lot of people on the trail that probably aren’t experienced hikers, i.e. inappropriate footwear and slipping after not paying attention to their footing - but also a lot of trail runners who’s mountain goat-esque skills will make you feel inadequate. A couple sections have ropes to pull yourself up, which is helpful. I flew my trekking poles out with me and they came in handy in a few sections.

hiking
15 days ago

Incredible views. Ran short on time so only made it to the second pillbox but views were amazing all the way up. Highly recommend this hike. Made it up to the second pillbox and back in about 45 minutes. We went just before dusk and sun was behind hills so morning\sunrise might be better yet!

hiking
15 days ago

The views are awesome. Good luck finding parking that’s anywhere near the road the trail is on. This trail is impossibly crowded. Please know, there’s a LOT of erosion and loose gravel. A woman slid today on one of the less steep parts, nearly breaking her leg. The constant use of this trail has resulted in poor hiking. Beautiful views, awesome pillbox, too crowded. I probably won’t do it again.

16 days ago

Awesome views but slippery when wet!

16 days ago

Great hike, not difficult, fun for the whole family. The trail was dry today making it even more enjoyable!

hiking
18 days ago

Difficult in the beginning but it gets easy. Best views of a blue ocean

19 days ago

I run this trail daily. Great exercise and incredible views. Fast trail. I run to second pillbox and back down in 15 mins.

21 days ago

Pretty good. Do the full loop, worth it

23 days ago

Great hike but steep entry and exit points if you go do the wholw trail so be wary of that

24 days ago

Beautiful views. Hike wasn’t too difficult but can be slippery going down even when dry. I slipped 3x wearing Nikes. Definitely recommend better shoes lol.

26 days ago

Loved it. Views are worth it. Not too difficult. Proper footwear is a must.

hiking
1 month ago

Overrun with tourists but well worth it anyway. Fantastic views --especially at sunrise.

1 month ago

One of the prettiest hikes we've ever done. Beautiful views all along the way. Wear tennis shoes as the trail is quite worn and would be slippery if it was wet. Parking is very limited, so prepare to hike a bit just to get to the hike.

We didn't do the whole trail, just to the second pillbox and back down. We started around 10 and there was a large crowd at the top. I bet this is beautiful at sunrise!

1 month ago

Harder hike than just moderate, but it is fairly short to the first pillbox. But holy crap it’s literally just a steep climb up rocks to get there.

1 month ago

what a great hike! incredible views! wear proper shoes!!!

1 month ago

If you want a hike that gives you views of the ocean and coast and not terribly touristy or hard, this is it.

* Steep from the get go. Bring actual footwear with grip
* Gets windy, people lost hats and shades. I almost did
* Past the second pill box is really overgrown. Bring a machete a wear long pants.

I went to the fourth "pill box" at the 1 mile mark is tiny compared to the first 3. (#1 is by itself, 2 and 3 are together) and after that the trail is really overgrown. I saw some folks ahead of me really struggling so I turned back as I didn't have a machete, or long pants.

hiking
1 month ago

Lovely 360 views, headed here for sunrise and was still quite busy. The trail on from the pillboxes was pretty quite. It rained while we were there and the path did get pretty slippy and would recommend shoes with a fair amount of grip. Also on the way down there is a lot of small paths branching off so use all trails to get back down. It was a Saturday and there was a guy in a car just before the trail head ensuring people don’t park there but there is plenty of parking along the road further on down.

hiking
1 month ago

Really great views!

hiking
1 month ago

Steep slippery trailhead. Beutjful views from the ridge.

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