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Chasing the Channel: The Pailolo Challenge Maui-to-Molokai outrigger canoe race

Posted on September 1, 2016

Story and photos by Fili Auro

Paddlers in the 2015 Pailolo Challenge approach the island of Molokai. Photo by Fili Auro.

On a Saturday morning near the end of summer, the sea vigorously pounds against the sands of D.T. Fleming Beach Park on Maui’s northwest coast. The beach is lined with nearly 100 outrigger canoes, their paddling crews meticulously preparing for one of the world’s great open-water canoe races: the Pailolo Challenge.

Spanning 26 miles from D.T. Fleming across the Pailolo Channel to the namesake pier of Kaunakakai town on Molokai’s south coast, the course of this entirely downwind annual race draws participants from around the globe. They are here this morning to test their fitness, paddling expertise and skill, and to catch the coveted “Hawaiian Sleigh Ride,” the downwind that race organizers say makes the Pailolo Challenge “the world’s funnest [sic] canoe race”.

The Pailolo Channel separates the islands of Maui and Molokai by a mere 8.5 miles at its shortest distance. Still, with its almost perpetual rough waters and intense winds slamming waves against canoes, it presents one of the most challenging channels in the Hawaiian Islands for outrigger paddlers. Such conditions make the Pailolo Challenge a huge draw for athletes, adventurists and thrill-seekers from around the world who find its demands enjoyable.

Outrigger canoes span the sands of D.T. Fleming Beach Park on Maui’s northwest coast on the morning of the 2015 Pailolo Challenge. Photo by Fili Auro.

Prior to the Pailolo Challenge’s founding by Hawaiian Canoe Club paddlers Rick Nu’u,  Mary Akiona, John McCandless, Kaimana Brummel, Reny Platz and current race director Darrel Belen, Maui canoe clubs largely used the channel as a training ground for major competitions. With the support of a couple of generous sponsorships, the inaugural Pailolo Challenge took place in 2007 with 25 crews paddling the channel.

Since then, the Pailolo Challenge has grown in stature. Its 2015 contest attracted 97 crews from across Hawai’i, the U.S. mainland and countries around the world (Canada, Singapore, Australia, Aotearoa/New Zealand, and American Samoa, among them) to participate. The challenge also boasts more sponsorships than ever before.

2015 Pailolo Challenge paddlers await the start of the race. The author calls this particular group of paddlers the “Pailolo Superheroes” because of their capes. Photo by Fili Auro.

“Right now we are the fastest growing race in Hawaii,” says race coordinator Arianna Gerry, a third-generation paddler and a Hawaii native who returned home after living in California. “The Pailolo Challenge is actually the race that really secured me wanting to move back to Maui in 2012. I fell in love with the race. How everyone helped me get my accommodations and logistics together is exactly how I want all paddlers to feel – like family.”

Walking D.T. Fleming Beach Park on race day, one can’t help but notice that Gerry has accomplished her goal. An extended ‘ohana of global paddlers stands together with hands clasped, bowing their heads in reverence during a traditional Hawaiian chant blessing participants, the land and sea, and the first Polynesian long-distance canoe travelers to Hawaii who made it all possible through epic and dangerous voyages across the Pacific. For a few precious moments, all are united as one and reminded to treat others as they wish to be treated, and to carry themselves with pride and dignity at all times as early Hawaiian ali’i (royalty) did in generations past.

A Kauai-based paddling crew pulls its outrigger toward the finish line at Kaunakakai Harbor on Molokai in the 2015 Pailolo Challenge. Photo by Fili Auro.

After the blessing is complete, paddlers shake hands and get situated in their canoes. All the months and lengthy hours of long-distance paddling, water changes and training has led to this moment, this day, on this alluring beach tucked away on the majestic Valley Isle of Maui. As the first paddlers take their canoes into the ocean and continue to the starting line, a few silently tip their hats in reverence to the kupuna (starting point). Then, blades are raised and all eyes are on Moloka’i across the channel.

Another Pailolo Challenge has begun.


10th annual Pailolo Challenge

Sat., Sept. 17, 2016

7:30 a.m.: Opening ceremony at D.T. Fleming Beach Park, Maui

8-9:20 a.m.: Races begin from D.T. Fleming Beach Park, Maui

Late morning: Canoes begin to cross the finish line at Kaunakakai Pier, Molokai

For more information, visit www.pailolo.com.


Fili Auro is a writer based in Lihue, Kauai. He has paddled in the Pailolo Challenge and Napali Challenge long-distance outrigger canoe races. The Napali Challenge covers 38 miles alongside Kauai’s majestic Napali Coast and west side from Hanalei to Waimea towns.

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