Kaiwa Ridge (Pillbox) Trail

MODERATE 591 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.

DISTANCE
1.6 miles
ELEVATION GAIN
800 feet
ROUTE TYPE
Out & Back

dogs on leash

hiking

trail running

views

wild flowers

wildlife

muddy

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
1 day ago

hiking
1 day ago

hiking
2 days ago

really nice views, but I did get several swarms of small insects stuck to me.

hiking
2 days ago

hiking
5 days ago

hiking
6 days ago

hiking
8 days ago

9 days ago

Fun trail that involves some mild climbing. My 9 year old loved it. My 6 year old finished but was pretty cranky by the end.

No parking available. Road side parking has been pretty much shut down. We went at 8:00 in the morning on a Saturday and found plenty of parking at Kailua Beach Park. Later in the day the Beach Park is packed and parking hard to find. This adds about 0.7mi to the hike each way (1.4mi total).

hiking
11 days ago

hiking
11 days ago

Sunrise :)

hiking
12 days ago

hiking
12 days ago

13 days ago

Breathtaking views.

13 days ago

16 days ago

hiking
17 days ago

Very steep all the way up to the first pillbox. Trail is unmarked and there are several branching paths, some of which are sketchier than others. Unfriendly locals on the street by the trail head. Confusing parking situation. I got a ticket while parked on the correct side of the street - apparently you're supposed to pull off the road onto people's property? Good views, but there are easier ways to see the same scenery.

hiking
17 days ago

hiking
18 days ago

18 days ago

hiking
21 days ago