Pailolo Challenge OC6 Race Information






Save the Date! We are excited to announce that the Pailolo Challenge is back on after a years’ long hiatus, we can’t wait to see you all there!

WHAT: The Pailolo Challenge is a 26-mile downwind race across the Pailolo Channel from Maui to Molokai

WHERE: DT Fleming Beach, Maui, to Kaunakakai, Moloka’i


Online Registration in state: Link to Hawaii Registration Form

Online Registration out of state: Link to Non-Hawaii Registration Form


Please download and review the Race Packet, Rules, Timeline and Safety Management Plan before registration

New exciting update to 2023 Pailolo

Separating the islands of Maui and Molokai, at just over 8 miles at its narrowest point, the Pailolo Channel is one of the windiest in all of Hawai’i. Get your crews and canoes ready for one of the most challenging channel crossing races in the Hawaiian islands, which has been nicknamed “the world’s funnest canoe race”.

We’re here to help take care of the logistics, while you get to focus on the fun and excitement that the Pailolo channel has to offer.

Fun aside, we are honored to host this race once again, and preserve the culture and tradition of those who came before us. We hope you have the opportunity to connect with the essence of the channel, the ocean, the Hawaiian islands, and the people. 

Mahalo to our sponsors and supporters – with their help we hope to make this the best Pailolo yet! More info to come about race day logistics, hotel discounts, and an after party to remember!

We hope to see you here on Maui this September!

As we all know, there are many factors that can have a negative affect our racing experience: equipment failure, poor nutrition, bad attitudes, or physical injuries. These are all things that we have somewhat control over and can prepare for. One thing that can have a HUGE impact, good and bad, on our race experience is the weather. Our sport relies on the weather conditions. We can have all our ducks in a row, perfect preparation, positive attitudes and we show up to the race and it is dead flat and not even a wisp of wind. But even with those kind of conditions, we still go out and charge. It’s just going to be HOT and definitely not as fun, but we go.

We all hope for wind and swells but there is a thin line between fun and dangerous. The Na Wahine O Ke Kai Race Officials were put in this exact position in 2015 and cancelled the most prestigious race in the Hawaii distance schedule. As race organizers, the safety of our paddlers is our number one priority. If we believe the conditions to be too dangerous for our paddlers, we will cancel the event. A similar situation arose in July 2016 when multiple associations’ Championship regattas were cancelled due to Storm Darby. In this case, permits were revoked from all events during the storm; completely out of race officials’ hands. In August 2016 after Darby, our Hawaiian Canoe Racing Association State Championship was also in limbo. It was not the weather conditions, but the quality of the water we would be paddling in. Officials did everything in their power to ensure a race for the paddlers. I applaud their efforts and commitment.

The Queen Lili’uokalani Race in Kona is this weekend. I do not envy the race coordinators preparing for the largest canoe race in the world as Hurricane Lester lingers just a few hundred miles away. I know they will do their best and make the smartest decisions for their paddlers.

As it seems like these type of situations have recently increased, the 2016 Pailolo Challenge Race Committee took a lot of time and consideration regarding how we would go about things if we were put in that situation. Our cancellation policy is stated on the website. With all event coordination, there are race expenses that are not refundable. This is why we have also stated that entry fees are non-refundable.

The Pailolo Challenge is unique in the fact that we are very limited by space. If you have done the race before, you know how tight the finish line is at Kaunakakai Harbor. We have reached capacity and the number of canoes and people the space can accommodate. We have also seen a increase in our race’s popularity. With the high demand and limited space, we have to ensure that registering crews are committed to racing, rather than holding a spot and dropping out over a crew who may not have made the cut off but had the funds and paddlers ready to race. This is another reason why entry fees are non-refundable.


We have two weeks until race day and there are no hurricanes or tropical storms in the forecast. As of today, we are looking at 15-20mph NE winds and some swells! Of course, nature has its own ways and can change in an instant.

Please check our Facebook Page and website for any race updates. Any and all race updates will be made directly on the website and FB. If it is not posted there, it is not true.

Paddlers, set you calendars for the 2014 Pailolo Challenge.
Saturday, September 13th 2014

See you on the water!

  • 1: THE DATE: Sat., Sept. 19, 2015

1 Week Before Na Wahine and 3 weeks before Molokai Hoe. The date makes the Pailolo Challenge a prime race in gearing up for Na Wahine o Ke Kai and the Moloka’i Hoe. The course offers fantastic training in surf conditions.


We provide towing on Maui and will also two your canoe to YB Kaunakakai if you need. Plus we coordinate with Na Wahine/Moloka’i Hoe to get your canoe to Hale o Lono.


The Pailolo Challenge is a great value. The $450 entry fee includes a great 26-mile downwind race, awards & goodies, AND a post-race party with food from the people of Moloka’i and brews from Maui Brewing Company. For iron crews that meet the experience level you can choose to go escort free, which saves in additional support and fuel costs. What a deal!

  • 4: MAUI NO KA ‘OI

Staying on Maui cheap AND luxurious. The Westin Ka’anapali Ocean Resort Villas is offering Pailolo Challenge participants an unbelievable deal on rooms! Check out their stunning rooms at:
Contact Hawaiian Canoe Club (please use contact form below) for the promotional code to secure your room today!


The Moloka‘i community benefits from the Pailolo Challenge. The Moloka’i High School Track Team will make money from feeding hungry paddlers at the post-race party. Local businesses benefit from purchases, car rentals, and night stays.