Kaiwa Ridge (Pillbox) Trail

MODERATE 712 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, walking, 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
610 feet
Out & Back

dogs on leash


trail running



wild flowers





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 hours ago

parking was difficult due tonroad closures and there were a ton of tourists that stand in the way of getting on top of the pillbox.

However the trail was gorgeous, and view was worth it on the top.

Awesome hike! It’s not difficult to hike!

7 days ago

Amazing sunrise views, a little steep at the beginning but otherwise a reasonable hike. Only took us about a half hour to get to the first and second Pillboxes. Would definitely do it again!!

10 days ago

Awesome hike. Started in the dark and saw a beautiful sunrise from the second pillbox. Very steep in spots, but would rate moderate. It did start raining on the way down which made it very challenging and slippery to get down. If you like a challenge and don’t mind getting a tad dirty this is your hike!

11 days ago

We parked few blocks away and walk to the entrance. Make sure your car is parked on the side of the road, wheels don’t touch the pavement. Great hike, I would rate it moderate. Easier than Olomana trail. Nice views, keep hiking pass the pillboxes. There were few families with the young kids. So it’s not very strenuous. Careful on the way down!

12 days ago

Very steep, slippery when wet. Stunning views!

15 days ago

Short, moderately steep hike with well-worth it views!! Beautiful!!

18 days ago

some challenging portions, great views. a solid intermediate level climb

21 days ago

You can actually hike all around the whole ridge. You can stay left and end up back in Lanikai beach or go right and end in the Kailua about a mile and a half from where pillbox started. I went left and love it. view just as good and almost no foot traffic

22 days ago

Incredible views. Will do this again.

25 days ago

Best one for a sunrise hike!

28 days ago

Beautiful view

Great hike, great views

1 month ago

Great view! Parking is limited and it gets crowded even on a weekday during low season so best to come really early.

1 month ago

This hike is seriously INCREDIBLE!! Beautiful views the whole way. The only two recommendations I would make would be to (1) leave early and (2) bring LOTS of water. We left later in the day so were very hot, and didn’t have enough water.

1 month ago

great views, pretty crowded

1 month ago

awesome views...a little on the harder side with a 1 year old on your back.

1 month ago

While the app says it’s okay to bring your dogs, please, please, please bring enough water for them!! Several dogs have died on this hike from heat exhaustion and dehydration.

1 month ago

Steep and in the beginning with lots of mud but you can hold on to the fence or trees so you don’t slide back down . After that part it gets more dry and it was pretty hot when I went with my kids (7 and 10). We ran out of water ( hadn’t planned on hiking) and turned around before reaching the top. That being said the view was still quite spectacular! Very well traveled, busy little hike. Will go go back to go all the way up.

1 month ago

Gets steep fast. But the views are incredible!

Load More