20 Great Oahu Hikes


(page 6 of 6)

The Bad-Ass Hikes


Kaau Crater.

Photo: david chatsuthiphan

Kaau Crater

Difficulty | *****
Length | 5 miles round trip
Wet/Dry | Wet

Can’t decide whether you want to conquer a ridge, a crater or a waterfall? Do all three! Beginning in upper Pālolo, navigate three waterfalls before reaching the crater’s rim and the marsh inside it that feeds them. Continue along the ridge for great views of both Waikiki and the Windward Coast. The going is steep, both up and down, but if you’ve ever dreamed of being in a scene from Lost, the climb is worth it.


Heading east on Waialae Avenue, turn left onto 10th Avenue. Proceed until Waiomao Road; take a right. Continue all the way until the end of Waiomao where the road continues on a narrower path. From here, the trailhead is accessible by foot, and the most convenient parking area is on the right across from a residence. (Note: Waiomao Road is divided into two segments by Halenoho Place. To reach the trail, continue on Waiomao when it becomes Halenoho, then turn left onto the second segment.)      



Heading west from Haleiwa on Farrington Highway, pass Camp Mokuleia and take the third entrance to Dillingham Airfield into the glider-pilot parking lot. The trail starts toward the hill here.

Kealia Trail & Access Road

Difficulty | *****
Length | 5 miles round trip
Wet/Dry | Dry

Get your cardio fix with 19 switchbacks that rise 1,000 feet up the hill behind Dillingham Airfield, followed by a steady two-mile incline. Distract yourself from the burn with views of Mokuleia and Haleiwa on the way up, and a stunning vista of Makua Valley waiting for you at the top. And if you can make it all the way up, going down will be a cakewalk.


Waianae-Kaala Trail.

Photo: cory yap


Traveling northwest on Farrington Highway into Waianae, turn right onto Waianae Valley Road. Continue until the road ends at the trailhead. Parking is in the gravel lot on the left.

Waianae-Kaala Trail

Difficulty | *****
Length | 6 miles round trip
Wet/Dry | Mixed

Your goal: the 4,000 foot tall summit of Mount Kaala, the island’s highest peak. Your starting point: the end of Wai‘anae Valley Road, elevation 1,000 feet. In between: paved roads, steep ridges, rock faces, a boardwalk trail, and panoramas of the Leeward Coast and the North Shore to Central Oahu. Not sure where you’re going? Follow the trees tagged with purple bottle caps up and the orange ones down. It doesn’t get any higher than this—on Oahu, at least.

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