Kaiwa Ridge (Pillbox) Trail

MODERATE 346 reviews
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Kaiwa Ridge (Pillbox) Trail is a 1.6 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 and trail running and is accessible year-round. Dogs are also able to use this trail but must be kept on leash.

1.6 miles 800 feet Out & Back

dogs on leash

hiking

trail running

views

wild flowers

wildlife

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.

1 minute ago

Beautiful trail! Visit on a clear day to get the best views.

hiking
4 days ago

This is a great trail to hike, and has one of the prettiest views on the island. The beginning has a little bit of a climb, but it is worth it. Definitely a good hike for families, you can climb in and on the pill boxes and dogs are allowed.

4 days ago

hiking
5 days ago

A nice hike that can be a bit dangerous without the proper shoes. I've done this hike 4 times. It's great for people slowly trying to increase intensity and learning to do more rugged hikes.

6 days ago

6 days ago

hiking
6 days ago

Beautiful, but difficult. Moderate for sure.

6 days ago

Beautiful, but difficult. Moderate for sure.

hiking
9 days ago

It was a bit crowded, but the views were incredible. My four year old grandson did the trail great with a few breaks. It's good to take water and a snack for kids.

11 days ago

hiking
13 days ago

hiking
14 days ago

Pretty good hike, not too strenuous, or steep. I noticed a lot of people struggling (more so on the way down) most of which where wearing flip flops which def. shouldn't be. Leads to old pillboxes with great views. It was loaded with tourists while we were there, which didn't really give you the opportunity to take it all in. The trails go beyond the look out and are well worth it. We saw a lot of different birds.

hiking
17 days ago

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hiking
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29 days ago

Beautiful view. Could see how it would be very slippery in the rain.