Kaiwa Ridge (Pillbox) Trail

MODERATE 181 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 587 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.

17 hours ago

One of my favorite hikes on the island so far. Me and my group of around 15 got to the top and halfway to the very end in around an hour. I wore my combat boots and had no problems but some of the group with worn tennis shoes slipped on the loose gravel. If it rains you're in for a very muddy experience because the whole trail is dirt and rock so be careful. If you're coming to Oahu for a vacation you should definitely try out this hike while you're here

hiking
4 days ago

9 days ago

hiking
12 days ago

Multiple routes and splits going up, so if one looks sketchy there's other options. (Did it with a dog and 5 year old)

hiking
12 days ago

Very fun! Did this hike with my family and dog. Nice view, don't miss out going all the way up!

17 days ago

Gorgeous views at the top! It's a quick, moderate hike. Challenging to find parking, but worth the hike.

hiking
18 days ago

This is beautiful and has great history but it's crowded and was t long enough for us. Once we got to the pillboxes we followed the trail further and explored other parts of the mountain, which was well worth it. There were basically no people on that portion and we got to see other parts of the island, which were pretty but there are more magnificent hikes on the Ohau. It spits you out into a neighborhood in Lanikai. It's a moderate hike, not too difficult or easy. Just right.

18 days ago

Loved it! Hiked with 3 kids (12, 4, 19 months). Backpacked the 4 y.o. And baby with no problem. 12 year old had no problem with trail. We climbed the left side because we enjoy more challenging hikes, but the right side is a better option for a beginner. Can be slick in spots just take it slow and pay attention especially if backpacking kids. Overall a nice quick and easy family hike, we were up and down in an hour. Views were awesome. Negative is that it is busy:(

19 days ago

21 days ago

Overrated and getting too crowded, but beautiful view of Lanikai at sunrise....

hiking
24 days ago

Went during one of the hottest and most humid days of my vacation visiting my sister, and I still managed to make it to the top fairly quickly.. with asthma mind you.. It's pretty rocky in some parts, I'd recommend wearing a decent set of shoes with good tread or hiking boots, BRING WATER, and there is a spot or two that the trail splits but goes to the same place... STAY RIGHT

24 days ago

Very Nice Views of Lanikai. This trail is a constant upward walk, very steep in areas but there is enough around you to grab onto to push on, the loose dirt and rocks make this seemingly easy hike a bit challenging at times, good shoes is recommended especially coming down "note, it didn't help me as a rock edge came loose and down I went, luckily I'm a guy and scars are manly right". So, if your worried about scratch or skid scars, you may want to wear long jeans "lol". I'm sure 90% make it up and down no problem, the other 10% like me get a little banged up, but nothing crazy. I seen three skidding down on there butts in areas but nothing that a little bubu kiss wouldn't cure. Enjoy, highly recomended.

hiking
25 days ago

Great adventure!! Really rocky and slippery especially when wet. Not recommended for kiddies on backpacks nor lil ones period. Flip flops NOT RECOMMENDED. Good hiking shoes recommended and HIKING POLES CAN BE helpful Wet or dry rocks can be slippery. AWESOME beautiful VIEWS ALONG THE JOURNEY To The PILL BOX.

hiking
26 days ago

Beautiful views in every direction. Not that challenging when the ground is dry, though I could definitely see how recent rain/mud could complicate that. I really enjoyed this as a quick up-and-back.

26 days ago

1 month ago

Great hike with insane views!!

1 month ago

The sunrise was amazing!!

hiking
1 month ago

Hiked up at 5:30 am with other early risers for a sunrise view at the pillbox. went to the second pillbox directly and it was incredible. The rain came through and brought the most colorful, closest rainbow I've ever seen. spectacular!

1 month ago

Great hike! Parking was not easy to find and the trail was a little steep, but it was a lot of fun. Recommend for ages 6 and up. Not good for toddlers or baby backpacks. GREAT VIEW!!!

1 month ago