Kaiwa Ridge (Pillbox) Trail

MODERATE 374 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.

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.

hiking
10 hours ago

Not a hard technical hike, but it is STEEP. It can be hot and windy (and muddy if it rained recently)...but the views are incredible!! When you are done go cross the street and jump into the ocean at Lanikai...a perfect way to cool off!!

hiking
14 hours ago

20 hours ago

butifull views, would recommend

1 day ago

2 days ago

Great place to watch the sunrise but come early

hiking
2 days ago

Nice and short hike- amazing view!

hiking
3 days ago

Don't go after rain - wait a few hours. The trail gets treacherous if it's too muddy and slippery! Otherwise great views of lanikai and Kailua and easy enough for beginners to do.

hiking
4 days ago

We did the whole hike of the 2 pillboxes and continued on past them to do the Ka'iwa Ridge to the end and down the other side and walked through town to our car. It was a fairly easy hike, we did it with our 8 year old son and had no issues but we are in quite good shape and are experienced hikers, even our son. Fabulous views, just super hot on a sunny mid day! Bring water

4 days ago

hiking
5 days ago

This trail is accurately named moderare, it is short but steep in some places. The trail gets a lot of traffic so I recommend going early for the sunrise. Looking east as the sun comes up behind the "Mokes" is a great view! The old military pillboxs are fun to climb on too.

hiking
5 days ago

hiking
5 days ago

Moderate is a good label. A few spots had a steeper incline while other areas had a shallow grade. The view is awesome. If you want to see the sunrise, arrive early as parking is only available along the left side of the road, away from the bike lane. We arrived at the top just after sunrise and were the 30th people to do so. I don't recommend wearing flip flops as there is some loose gravel. Also, it may be slippery when wet. Most people didn't even bother to bring water with them, but I was glad to have some. It's not very far to the first pillbox, but if you keep going you can reach the second pillbox within another 10 minutes. The trail continues on after that, so if you have time keep on going!

6 days ago

hiking
6 days ago

If you take this trail from the pillbox entrance all the way around to the other side of Lani Kai beach it's 2.0 miles ONE WAY. The two pillboxes are within the first 1/4 of the entire thing. Challenging but a great hike for someone looking for a bird's eye view of the east side of Oahu and Kailua :)

It can get hot but the breeze is nice. If you park near the entrance to the pillboxes you're looking at about a mile walk back to your car if you take the ridge around one way.

hiking
7 days ago

9 days ago

Beautiful view

10 days ago

Beautiful

14 days ago

18 days ago

Amazing