Hiking on the Windward Side of Oahu, Hawaii ( Hiking Trails)

Hiking on the Windward Side of Oahu, Hawaii ( Hiking Trails)

Windward Oahu Hikes pill box- lani pillbox shutterstock_144667880

Old Pali Hwy Trail

While this hike is not technically on the windward (east) side, it is a can’t be missed highlight for any who want a magnificent view of Windward Oahu and the Nuuanu Pali! It is rated as an easy hike of about a mile, but you will need tennis shoes and the trail can be steep. As you drive up the Pali Hwy., Hwy 61, from Honolulu, you will come to the Nuuanu Pali Lookout. From here you can see Kaneohe, Kailua, and much of the Windward Coast. The Old Pali Hwy Trail winds down from the right side of the lookout. Since you are at about the 1200 ft level it can be cool, sometimes rainy or wet, and always windy. Bring a jacket and take it slow, enjoying the views which often include some great waterfalls! When you reach the end of the trail, by the large boulders, just circle back up and do not continue on the lesser traveled dirt trail that winds down between the boulders. The dirt trail leads 10 miles down, to Waimanalo, and is for experienced hikers! After your hike, you can continue on the Pali Highway over into Kailua.

Lanikai Pillboxes (Kaiwa Ridge Trail)

This moderate hike is only about a mile, but it’s a steep climb so be prepared. The reward is worth it! You will have an incredible view on the journey up, and don’t stop when you reach the first pillbox (other than to take in the view of Lanikai and the Mokulua Islands), because the best view is from the second pillbox. These pillboxes were built during World War II and you can easily see why, since the location offers sweeping vistas of the Windward coastline! From the second pillbox you can see all the way from the Makapu‘u Lighthouse on one end to Mokoli‘i Island (Chinaman’s Hat) on the other. When you first start out on the trail, don’t get discouraged by the underbrush you have to get past, as the trail opens up after about 10 yards. Depending on your pace, the hike takes about an hour up and back. Once you reach the second pillbox, turn around and travel back down to where you started. To get there head towards Lanikai Beach in Kailua. Once on Kailua Street you will go until you reach Kawailao Street and turn right. This street becomes Aalapapa, so don’t let it confuse you, and you will turn right off this street onto Ka‘elepupu Drive. You will see a few parking spaces on the right hand side by the Mid-Pacific Country Club. Park and walk to the side street on the left and look for the small “Pillbox Hike” sign. Remember…wear good hiking shoes, bring water, and when you reach the top, enjoy the impressive views!

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