Kaiwa Ridge (Pillbox) Trail

MODERATE 446 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


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.

44 minutes ago

short hike with great views. steep at times and generally crowded. there is no shade and in along the trail so bring lots of water and sun protection

3 days ago

Quick and easy hike. Go early in the morning to catch an amazing sunrise over looking the mokes!

6 days ago

Great trail! No shade but the breeze helps a lot. It is steep but short and you can see the 2nd pillbox from the first one so you can decide whether you want to make that second climb. Awesome views. Bring water and (reef safe) sunscreen!

6 days ago

love this hike. took the puppies today. but it got pretty hot after the first photo spot.

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15 days ago

My favorite hike so far! Not too hard as long as you take your time. I've done it twice and I love it. Make sure to bring plenty of water! The beginning is the hardest part. Once you make it past all of those trees it's gets easier and is more of a gradual incline I think.

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27 days ago

Great trail with an awesome view. Tough for the youngest (5 years old) but she made it