Aloha! Welcome

The Pailolo Challenge is a 26 mile race from DT Fleming Beach, Maui,  to Kaunakakai, Moloka’i. Paddlers gather from Hawaii, USA, Canada, Australia and more to test themselves in excellent channel crossing conditions.

Since inception the race has caught on and considered to be the most consistent and funnest canoe race in Hawaii. Join us!

Hawaiian Canoe Club

Pailolo Goes Green

Mahalo to Sustainable Island Products for sponsoring the Pailolo Challenge 2019! They will be providing compostable alternatives to single use products for our after party! We will also have a reef-safe sunscreen station at the race start. We strongly encourage the use of reuseable water coolers, jugs and packs.

In addition, Moloka’i Athletics will be providing waste stations for recyclables, compost (mahalo to Sustainable Moloka’i – Sust-aina-ble Moloka’i for your kokua) and hopefully very little trash. We hope to minimize our impact on the landfills and ‘aina!


Mahalo Sponsors

We greatly appreciate the sponsors who support the sport of our ancestors and help us do what we love to do. We hope that you will support them in return by considering their service and products.
If you are interested in sponsoring The Pailolo Challenge, please use the contact form below or complete the Pailolo Sponsorship Proposal

The Worlds Funnest Outrigger Canoe Race

Cross The Channel
Strong Competition
Prepare for Kaiwi
Discover Molokai
It’s About Fun

Join us Saturday September 19, 2020 for the 2020 Pailolo Challenge.



Important Event Information

Online Registration & Payment expected to start May 2020.

Race Date: Saturday, September 19, 2020

Check-In and Coaches’ Meeting (Mandatory): Friday, September 18, 2020

Get your crews and canoe’s ready for one of the gnarliest channels in the Hawaiian islands, and what is being called the worlds funnest canoe race. Why? We help take care of the logistics, while you get some great downwind training and experience in the most consistent channel… PAILOLO.

Thanks to our sponsors and supporters we also show you a good time, hotel discounts, big after party, and you don’t need to book a flight back to Maui, take the ferry!

Fun aside, we are honored to host this race and follow in the tradition of our ancestors. We hope you also have the opportunity to connect with the essence of the channel, the islands, the ocean and the people. You know, the name of the channel itself holds significance in its meaning, to raise and encourage expertise and skill. A perfect testing ground for the following races in the Ka’iwi channel between Moloka’i and Oahu.

We hope to see you here on Maui and we will do all we can to accommodate your needs during your stay and travels.

Pailolo Race Course

Young Brothers – Canoe Delivery


Mala Boat Ramp




Race Start – DT Fleming Beach


Finish Line – Kaunakakai Harbor


Maui Brewing – Awards and Celebration