Kaiwa Ridge (Pillbox) Trail

MODERATE 846 reviews
#1 of 3 trails in

Kaiwa Ridge (Pillbox) Trail is a 2.9 kilometer moderately trafficked out and back trail located near Kailua, Oahu, Hawaii that features beautiful wild flowers and is rated as moderate. The trail is primarily used for hiking, walking, trail running, and nature trips and is accessible year-round. Dogs are also able to use this trail but must be kept on leash.

DISTANCE
2.9 km
ELEVATION GAIN
198 m
ROUTE TYPE
Out & Back

dogs on leash

hiking

nature trips

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
1 hour ago

this was a great hike! It was definitely a challenge but the view was totally worth it! highly recommend!

hiking
18 hours ago

Good trail, fairly short. Very busy even in early morning. Super muddy. Slide down the trail muddy, ropes that your supposed to be able to use to climb down but those are muddy too.

2 days ago

I dug it alot, kinda short though

hiking
2 days ago

Awesome hike....highly recommend

hiking
muddy
over grown
rocky
washed out
3 days ago

Very muddy, and steep, this is not for the faint of heart. Awesome views but you have to work to get there. Very muddy due to the recent rains.

hiking
rocky
4 days ago

Super cool small hike to do. Great view all around. Start off from the get go, gets easier after that. Super fun!!!

hiking
over grown
rocky
4 days ago

Great hike over all. In the end it’s rocky going down that’s for sure. But sturdy tree to hold onto.

hiking
5 days ago

Beautiful views but not marked very well and easy to get off trail.

hiking
muddy
6 days ago

hiking
muddy
8 days ago

This was a very fun little hike in Lanikai. The path is rocky - it took me about 20 minutes to run up the trail to the top. I loved the view of the Na Mokulua from the lookout point. The workout was needed as well, but you have to navigate some muddy trails on a rainy day. I highly recommend this hike! Mahalo!

hiking
10 days ago

Great views!

22 days ago

This hike was a ton of fun. It had just the right amount of challenge bc of the scramble. The views were beautiful. There are multiple paths all next to each other so you dont really have to wait on other hikers. Wear sunscreen. Do not attempt after a heavy rain. It would be dangerous. This was one of our favorite hikes all week.

hiking
23 days ago

Fun to hike with friends and family. Best to see it when the sun is coming up. I would recommend doing it when you have family visiting for a view days. Very beautiful!

hiking
muddy
no shade
25 days ago

27 days ago

Summit is absolutely stunning. I was saddened by the condition of the trail and destruction of such beauty to continue unchecked. I am a new resident to Kailua and hope we can do something to save this land and the waters affected by the poor management of this trail.

hiking
no shade
rocky
scramble
29 days ago

I started from the main trail head , up the pillboxes, and continue until I got off the hills next to Kamahele St.

hiking
rocky
1 month ago

One of my favorite hikes on the island! Incredible views, quite rocky, challenging at some parts, especially the beginning as it is quite steep. Just take your time though. It cautions hikers with dogs but I can see dogs being able to complete the hike just consider the weather and pack plenty of water! It is heavily trafficked throughout and especially at the first and second pillbox... but if you trek on just a little further there is a spot with a large rock that you could have all to your own! Which is what we did! I think this hike may be difficult for kids and elderly but again, just take your time!
TIP: After hiking, head down to Lanikai beach to relax and soak up the sun. 0 waves & turquoise waters!!

hiking
1 month ago

This’s a decent hike. Way too many people on it trying to catch the Sunset leaving very little Realestate to call your own unless you arrive super early. Head lamp is helpful if you’re going up and it’s still dark outside. After watching the sunset we continued on and around to the other end of the trail. It’s difficult going down and so pray it’s dry or hasn’t rained a few days. The views are beautiful.... But the hike is okay and a decent workout going up and down the trail with decent views.

hiking
no shade
1 month 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
1 month 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.

1 month ago

Amazing view!

hiking
1 month ago

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

1 month 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
1 month ago

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

hiking
1 month 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
1 month 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.

1 month ago

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

hiking
1 month 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 :)

1 month ago

Nice view to the beach and mountains!!

hiking
1 month 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.

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