I was crunched for training time this morning so I decided to keep my ride short: Aiea > Honolulu > Makapu’u > Old Pali Highway > Honolulu > Aiea. I rode with a team mate to Pali, then he continued his lap of the island. I chose to take the short route over Pali towards town, typically disliked by cyclists as it can get a bit sketchy riding uphill around blind turns with cars whipping by. I’ve ridden Pali town-bound 100′s of times thanks to spending a year living in Laie and commuting 37 miles each way to town, but today I figured I would go up the less traveled Old Pali Highway.
Right after the last set of traffic lights on the Kailua side of the Pali there’s a road on the left. It goes from paved and clean, to paved and very mossy, eventually becoming only a few feet wide before transitioning into more of a hiking trail than a road. A quick hike under both lanes of the Pali, you exit up a crappy looking but structurally sound ladder, hike a bit more, then back onto a section of old road that takes you to the touristy Pali Lookout above the tunnels.
The Pali is one of my favorite places to ride… Possibly down to the amount of times that I’ve ridden it or hiked around the area. It also has a very long history. It was the location where King Kamehameha I fought O’ahu’s Kalanikupule in the famous Battle of Nuuanu. In the early 1800′s it was merely a treacherous trail that required the use of ladders and ropes to be navigated. It was much narrower and steeper than the route that exists now, and I was used by people wanting to cross the Pali to sell poi, pigs, sweet potatoes, and fruit in Honolulu.
In 1897 the road had been reduced to an 8% grade and widened to 20ft thanks to 10,000 pounds of dynamites and 17,500 pounds of blasting powder. During construction of the road workers found an estimated 800 skulls and other bones from the Battle of Nuuanu.
The current Pali Highway was completed in 1957 after 5 years of work that included blasting rock to create the tunnels. The Wilson tunnel, opened in 1960 after problems with cave-ins and other accidents was named after Johnny Wilson who had worked on the Pali Road in 1887. Once the road was complete the windward side of O’ahu has its biggest population increase between 1960 and 1970.
Here are a few photos from the ride:
Sunrise from Diamondhead.
Pali Highway with the Old Pali Highway above. The lookout is to the right but out of view.
Underneath the townbound lane of the current Pali Highway.
This is where you have to climb up a ladder with your bike.
Part of the old Pali Highway now closed to vehicular traffic.
The view of windward O’ahu from the Lookout.

“Pali Road and cliffs, Honolulu, Hawaii” ca. 1883-85. Photographer: Vandis Expedition.
Photograph courtesy of the Bishop Museum.


















