Kaiwa Ridge (Pillbox) Trail

MODERATE 206 reviews
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Kaiwa Ridge (Pillbox) Trail is a 1.6 mile moderately trafficked out and back trail located near Kailua, HI 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 877 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.

20 hours ago

1 day ago

For the first trial in Oahu, just perfect! Easy and with a beautiful sight!

3 days ago

hiking
4 days ago

Nice ease trail. historical locations

hiking
14 days ago

19 days ago

Good hike! Some traffic but worth it.! My boyfriend and I did it barefoot like we usually do on hikes and was easy!

24 days ago

Great trail. Steep in a few parts and sheer cliff on both sides at the end, but damn was it a great view. Worth it!

hiking
25 days ago

good short hike...

hiking
25 days ago

good short hike...

25 days ago

26 days ago

Wake up early and catch this trail as the sun rises, give yourself a minimum of 30 minutes to reach the top so you are not rushed and can grab a seat, yes a seat. It was very busy on a random weekday so get there early. Worth the wake up and be patient in the way down for slow people. Oh, saw tons of dogs on this trail, like really small dogs so if you think it's difficult, it's really not because a 3lb dog happily made the venture up.

hiking
27 days ago

I hiked this trail early this morning before sunrise. It was super easy, and watching the sunrise while sitting on a pillbox was awesome. I started walking up someone's driveway at first, but they had signs posted saying "YOU PASSED THE PILLBOX -------->" The trail is clearly marked, but in the dark you might not see it at first.

hiking
1 month ago

This is my favorite trail that I've done on Oahu so far. My boyfriend and I woke up early this morning to hike up before sunrise (we allotted ourselves an hour, but made it in slightly over half the time). The incline is steep, but take your time and find your footing. If you go early, as we did, make sure you take a flashlight, or use the one on your phone. It's difficult to find sturdy ground without a light. The sunrise was stunning and we had a great time exploring the pillboxes afterward. Be aware of loose rocks and dirt, especially on the way down. It's easy to slide and fall. It wasn't too crowded, but getting there early ensures good parking (we parked a block away on the street) as well as a good spot to watch the sun.

1 month ago

Great hike! Very beautiful views. Older people may have a problem with the footing because of the loose dirt on the rocks.

1 month ago

hiking
1 month ago

1 month ago

Beautiful view. Hiking with 80% of easy rock to climb, could be no so easy for young kids and aged people.

hiking
1 month ago