Kaiwa Ridge (Pillbox) Trail

MODERATE 822 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.

7 minutes ago

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

1 day 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 day 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.

5 days 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
5 days ago

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

6 days ago

http://tinyurl.com/y8ts7grw

hiking
8 days ago

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

hiking
10 days 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
13 days 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.

hiking
18 days ago

According to alltrails logged recordings, the number one most recorded is Koko Crater stairs at 992.
2. Diamond ‘Leahi’ Head- 880
3. Manoa Falls- 762
4. Kuli’ou’ou Ridge State Trail- 582
5. Aiea Loop State Trail- 565
6. Lulumahu Falls - 560
7. Makapu’u Point Lighthouse- 550
8. Maunawili Falls - 502
9. Kaiwa Pillbox - 500
10. Waimano Falls- 405

1 month 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

1 month ago

Good easy hike. Great at sunrise

1 month ago

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

1 month 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.

1 month 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
1 month 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
1 month 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
2 months 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.

2 months ago

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

2 months 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
2 months 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.

2 months 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.

2 months ago

Maintenance has been postpone till further notice.

hiking
2 months 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!

2 months ago

Good sunrise, million people with speakers blaring though.

2 months ago

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

3 months ago

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

3 months ago

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

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