Kaiwa Ridge (Pillbox) Trail

MODERATE 400 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.

1 day ago

5 days ago

Hello! I do hikes and photos out here on the island. Feel free to check out my Instagram Mike.Karas and shoot me a message if you have any questions/are interested in hiking. You can email me as well at mikekarasphotography@gmail.com.

hiking
8 days ago

8 days ago

Great hike. Do it for sunrise. About 30-40 minutes to get to the top. Not a paved trail. Awesome views.

hiking
13 days ago

Great view after steap short hike.

hiking
15 days ago

15 days ago

17 days ago

18 days ago

This trail never gets old. The views of the mokes and mountains are always worth it. Sun and Moon rises are breathtaking from here. please don't litter.

hiking
19 days ago

Awesome hike. Climb is steep and rewarding. Photo opportunities from many angles. Hike past the second pillbox to the next rise and you get another breathtaking view!

20 days ago

Very pretty views at the top. Pillboxes would be fun for kids to play in. The hike to the top is in open sun, so it's best not to do this one in the middle of the day in my opinion. But the hike to the top is very easy and is a good family adventure.

21 days ago

beautiful

hiking
22 days ago

hiking
22 days ago

23 days ago

Very easy hike with beautiful view. This place is very popular, so it will be many other hikers.

23 days ago

easy

23 days ago

this trail is very easy but great if you're looking for a quick hike that has a great view of the ocean.

hiking
24 days ago

24 days ago

24 days ago

Aloha! I do hikes and photos out here on the island. Feel free to check out my Instagram Mike.Karas and shoot me a message if you have any questions/are interested in hiking. You can email me as well at mikekarasphotography@gmail.com.