Kaiwa Ridge (Pillbox) Trail

MODERATE 537 reviews
#1 of 3 trails in

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.

DISTANCE
1.6 miles
ELEVATION GAIN
800 feet
ROUTE TYPE
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.

hiking
1 day ago

hiking
1 day ago

hiking
1 day ago

I would say this trail is difficult, not moderate. Definitely wear appropriate shoes, as it has slippery sand parts as well as rocky parts, AND it is very steep at times.

hiking
2 days ago

hiking
2 days ago

hiking
3 days ago

4 days ago

Easy - great views!

hiking
5 days ago

hiking
6 days ago

hiking
6 days ago

hiking
7 days ago

hiking
7 days ago

Beautiful views. Even if you don't go all the way up.
Our 3 year old needed help along the way but stopped short of the top because of the steep rocks just before reaching the top. Our 6 year old was able to go all the way with help at a few places.

7 days ago

This hike has gorgeous views and a fairly decent breeze. Be aware that it is an extremely heavily trafficked hike and there is loads of people here, so parking can be harder to find. Would also recommend continuing along the path along the ridge line to continue seeing the beautiful views, however you will have to walk through town to get back to where you parked.

hiking
8 days ago

hiking
8 days ago

Solid hike, probably less than 2 miles out and back. The beginning is hardest just that it can be slippery because of the dirt and it being so steep. There is rope to help you here and it gets easier all the way up to the Pillboxes. We parked at Lanikai Beach and walked half mile to the trailhead as parking in the neighborhood is hard to come by. Beautiful sweeping views on the top so it is easily recommended and pretty quick to do.

hiking
10 days ago

This hike is amazing. Steep climb with rewarding views. Make it to the pill box and the view is breathtaking.

hiking
10 days ago

10 days ago

Insane trail. Super fun, but very dangerous at the same time - granted I was running along the edge of the cliff the whole time. But there are options for hiking along the edge or just off from the edge. Still dangerous either way as a strong gust of wind could easily throw you over the edge.