
The first person to make a solo crossing in a kayak from Molokai to Oahu was OCC member Dale Adams in 1976. Two years later, Adams started the Kanaka Ikaika Molokai to Oahu Kayak Race and Outrigger members have participated ever since. Eve Anderson was the first woman to paddle a kayak across the Molokai Channel in 1980, finishing 12th. Marshall Rosa, Mark Buck and Bill Mowat were also early channel crossers, with Rosa finishing second in 1982, 1984, 1986 and 1988.
Other members who have entered and finished well are Kala Judd, Mark Sandvold, Tommy Conner, Steve Van Lier Ribbink, Chris Kincaid, Geoff Graf, Tom McTigue, Courtney Seto, James Kincaid, Nalu Kukea, Randy Grune.

Lesline Conner won the women’s division in 1987, 1989 and 1990, was second in 1992, and third in 1993. Kelly Fey won in 1996. David Buck won the 18 & Under Division in 1992 and Nalu Kukea was second overall.
The race starts at La`au Point on Molokai and finishes at Koko Marina in Hawaii Kai, a distance of 32 miles.
Read more about the races in articles below that have appeared in the Outrigger magazine. Results may also be found in For the Record.
Molokai Challenge & Surfski World Championship
2014
Jimmy Kincaid/Ivan McIvor, 2nd SS1 Relay 2 Paddlers, 5:00.52
Aukai Manson/Kimo Brown, 3rd Male 39 & Under Relay OC1, 5:09:16
2015
Patrick Dolan, 1st SS1 Solo M19-29, 3:54:59
Kaihe Chong, 1st OC1 Solo MOpen, 4:06:32
Jimmy Kincaid/Ed Joy, 7th SS1 Relay Open, 4:20:51
Cheyne Mench, 1st OC1 Solo M19-29, 4:27:31
Aukai Manson/Tyler Silva, 1st Junior SS1 Relay, 4:27:46
Matt Mench, 2nd OC1 Solo M19-29, 4:34:24
Mary Smolenski, 1st OC1 Solo W Open, 4:58:44
Vaimana Conner, 2nd OC1 Solo M30-39, 4:59:03
2016
Aukai Manson/Alex Lee/Nainoa Orr, 3rd SS1 Relay, 4:08:54
Kaihe Chong, 1st OC1 Solo M19-29, 4:26:51
Patrick Dolan/Ryan Dolan/Tim Dolan, 1st, OC1 Relay 3 paddlers, 4:11:08
Nat Yee/Francesco Forti/Tyler Silva/Keapo McKenney/Magnus Spotter/Adam Sandvold, 1st, Jr OC2 Relay 4 paddlers, 4:24:19
Hunter Pflueger/Riley Kawananakoa/Maverick Aipa/Schuyler Cole/Isaac Miller/Max Pflueger, 2nd Jr OC2 Relay 4 paddlers, 4:25:39
Noa Kerner/Peter Cross/Kaimana Gomes/Chase Swanson/Nick Dworshak/Evan Lee, 3rd Jr OC2 Relay 4 paddlers, 4:31:33
Kala Diaz/Ethan Siegfried/Craig Riley/Bryce Meichtry/Parker Murray/Kaohu Kamakawiwaole, 4th Jr OC 2 Relay 4 paddlers, 4:34:17
Hobey Moss/Ryan Funk/Jeffrey Spencer, 1st Jr SUP Relay 14′ and under, 5:53:44
2017
Aukai Manson/Zsolt Szadovszki/Alex Lee/Nainoa Orr, 1st SS1 4 pax, 3:57:43
Pat Dolan, 1st SS1 Solo M19-29, 3:58:16
Mike Pedersen/Wyatt Jones/Heath Hemmings, 1st OC1 Relay M19j-49, 4:20:38
Gabriel El Hajii/Blaise Espiritu/Liam Esteban, 2nd OC2 Relay, 4:47:50
Indar Lange, 1st OC1 Solo M30-39, 4:49:30
Todd Bradley/Dave Parmenter, 2nd OC1 Relay M50-59, 4:55:48
2018
Pat Dolan, 2nd SS1 Solo, M30-39, 3:17:57
Tuarongo Cowan, 2nd OC1 Solo, M19-29, 3:43:28
Heath Hemmings/Jim Foti/Chris Maynard, 1st OC1 Relay 3 M40-49, 3:55:25
Harrison Deisroth/Isaac Blake/Kaiko Torres De Sa/Aukina Hunt, Blaize Nourrie/Evan Lee/Zachary Ingram, 1st OC2 Jr Relay, 3:58:35
Tyler Silva/Kaihe Chong/Diego Hancock/Parker Murray/Kekai Delmendo/Adam Krivatsy/Kaimana Drago/Gavin Kondo, 1st OC2 Relay M Open, 4:12:35
Hunter Pflueger/Isaya Ady/Max Pflueger/Jack Maurer/Blaise Espiritu/Kaimana Gomes/Christian Papapa/Jonah Johnson, 2nd OC2 Relay M Open, 4:18:25
Gaylord Wilcox/Jimmy Kincaid/Fred Atkins, 3rd OC1 Relay, M64+, 4:41:41
2019
Patrick Dolan, 2nd SS1 Solo M30-39, 3:13:00
Christian Bradley, 6th OC1 Solo M19-29, 3:56:49
Victor Bovino Agostini, 2nd OC1 Solo, M40-49, 4:07:58
Billy Balding, 1st OC1 Solo M50-56, 4:16:21
Ariana Hunt/Malia Winter/Taihere Thompson/Marissa Kuriyama/Sky Ross/Sophia Galaida/Emma Simmons/Hie Loui, 1st OC2 Jr Female Relay, 5:01:57
Emma Daniels/Kiani Yost/Kaya Lee, 1st, OC1 Relay Female, 5:01:40
Marc Haine/Mark Rigg/Chris Kincaid, 3rd OC1 Relay M50-69, 4:18:40
Travis Grant/Hunter Pflueger/Sebastian Ako/Seth Allen/Tupuria King/Jack Mauer/Nikolaus Steiner/Hobey Moss/Kekai Delmendo/Heinere Itchner/Stryder Garrett/Kai Binney, 1st OC6 Junior Relay, 3:47:17
Kaihe Chong/Harrison Deisroth/Bronson Napoleon/Nathan Kane/Gunnar Grune/Winston Ako/Isaac Blake/Diego Hancock/Tuarongo Cowan/Noah Clark/Blaize Nourrie/Adam Krivatsy, 2nd OC6 Junior Relay, 3:54:58
2024
Patrick Dolan, 2nd Overall SS1 Male, 3:45:04
Jackson Monahan, 1st, SS1 M18&U, 5:12:04.04
Victor Bovino Agostini, 1st, SS1 M50-57, 5:05:13
Becky Needham/Maile Villablanca, 1st OC1 Tandem Relay W19-39, 5:27:46
Makena Orr/Katherine Donnelly/Chloe Heahlke/Remy Ah Quin, 2nd, OC2 Relay, 6:07:55
Marc Haine/Chris Kincaid/Ron Grabbel/Guy Wilding, 1st MC2 Male Relay, 5:34:58
OCC Magazine Articles
1980-12 OCC Paddlers Participate in Kayak Races
1982-11 Molokai to Oahu Kayak Race
1984-11 Marshal Rosa 2nd in Molokai
1986-03 Kayaking Highlights 1985
1986-07 OCC Kayakers Impressive in Molokai Oahu Race
1988-07 Molokai to Oahu Kayak Race
1989-07 Chalupsky Wins Molokai Race Again
1990-07 A Personal View of the Molokai Kayak Race
1990-07 Outrigger Kayakers Challenge Molokai
1991-07 3 Molokai Channel RacesTest 1-man, kayak, sailing canoes
1992-08 1992 Bankoh Kayak Challenge
1993-07 Judd, Graf First Hawaii Finishers in Molokai Kayak Race
1995-05 Molokai Kayak Challenge May 21
1996-07 Bankoh Molokai Kayak Challenge
2010-07 Mark Sandvold 1st Hawaii Finisher in Molokai World Championships