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A stunning, short trail along the Ka’iwa Ridge with view of Lanikai and Kailua, offering some of the best vistas of Oahu’s windward side.

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Mileage: 1.6 miles
Elevation: 587 feet
Difficulty: Moderate
Duration: 1 hour to 90 minute round trip depending on how far you decide to go.
Type: Out and Back or Loop, you can decide
No bikes, Dogs allowed on leash.

The Trail:  The official trailhead is unmarked and begins with 40 feet of uphill, paved, private driveway along Kaelepulu Drive.   The driveway is just opposite the Mid Pacific Country Club and Golf Course.

As you begin, the trail is undeveloped, very steep and loose gravel can be slippery.   There are no guardrails here. But stay focused, because once you get through this section, you are rewarded with stunning views very soon.

The trail winds around to a pillbox or a concrete dug-in guard post.   You will be able to see the Mokulua Islands, Kailua Beach and Lanikai Beach from the first pillbox or concrete dug-in guard posts.   In about 10 minutes, you will arrive at the second pillbox.  Here, you can turn around and return to where you started.   Or you can keep on trekking for another 30 minutes which will take you further around the coast down to A’alapapa Street where you can walk back about half a mile to Ka’elepupu Drive, where you started.

Make sure to wear good hiking shoes as there is a lot of loose rock and gravel to slip on.

How to Get There: Take the H-1 Freeway from Waikiki and go west. Merge onto the Pali Hwy (Hwy 61). Turn right on Kailua St (in the town of Kailua). Make a right turn onto Kawailao St and follow it until it becomes A’alapapa St. Make a right turn onto Ka’elepupu Dr. There are about 7 parking spaces on the right hand side by the entrance gate to the Mid Pacific Country Club. Park and walk up the side street on the left and look for a small sign for “Pillbox Hike.”

There are about 7 parking spots located on the right hand side by the entrance gate to the Mid-Pacific Country Club.  Park and walk up the side street on the left hand side and look for the small “Pillbox Hike” sign.

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