Each May, the world's best surfski and solo canoe paddlers enter the ocean at Molokai's Papohaku Roadstead to compete in the Molokai Challenge -- The World Championship of Open Ocean Surfski and Solo Canoe Racing. The year's race is scheduled for Sunday, May 21 and begins at 8:00 am.

Organized by Kanaka Ikaika Racing Association, Hawaii's oldest organized kayak association, the race is sanctioned by USACK.

The Molokai Challenge, originally named Kanaka Ikaika, is the ultimate Ironman and final test of paddling skill, endurance and knowledge of ocean surfing. It tests a paddlers ability to maneuver against unpredictable weather conditions in the Kaiwi Channel.  The Kaiwi Channel, more often called the "Molokai Channel" is an expanse of ocean beginning at Laau Point on Molokai and ending off Diamond Head on Oahu. It is considered one of the roughest ocean channels in the world.

The solo invitational event begins in the waters off Papohaku Roadstead off the Kaluakoi Hotel and Golf Course near the west end of Molokai and finishes inside the marina at Hawaii Kai Koko Marina on Oahu, 32 nautical miles away.

The 2006 race is the 30th annual crossing, counting the 1976 solo effort by Kailua physician Dale Adams. Adams called his crossing "the challenge of the day," but it has since developed into the premier long-distance, open ocean, solo crossing in the world.

1976 ~ Adams paddled for 7 hours, 30 minutes in his first effort. He repeated the crossing a year later with Dean Hayward, a marathon runner and coach at Kamehameha Schools, and Jorgen Hansen, a veteran international surfski paddler. Hayward finished first in 6 hours, 45 minutes. 

1977 ~ Adams consulted Hawaiian linguist Pilahi Paki who described the effort as "Kanaka Ikaika," which literally translated means:

Mankind's respectful challenge of the great, mighty ocean.

Paki's name for the race also became the name of the paddling club.

• 1978 ~ Kalai Handley of Kailua, Oahu, won the race and since that time no other male competitor from Hawaii has finished first in the surfski division.
  
  
• 1979 ~ 18 Entrants Finished
  Paddlers made the crossing, including the first international competitor, Grant Kenny of Australia, who won the race in 5:37:05.
  
  
• 1980 ~ Eve Anderson became the first female competitor and Chuck Bennett, a paraplegic, was the first physically challenged entrant.
  
  
• 1988 ~ 45 Entrants
  The 1988 race attracted 45 competitors from Australia, Hawaii and South Africa.
  
  
• 1989 ~ 67 Entrants (44 Entrants Finished)
  South African champion Oscar Chalupsky, who posted his 7th straight victory with a time of 3:39:47 and Greg Barton American Olympic Gold Medallist.
  
  
• 1990 ~ 58 Entrants Finished
  Bronze Medallist Grand Kenny made a successful return to the winners circle, crossing the channel in 3:44:45 for his firth win.  Tahiti-born Lesline Conner of Waimanalo won the race for her fourth time.
  
  
• 1993 ~ Three time women's winner, Jane Hall, from Sydney, Australia, set a new women's record in a time of 4:14:23.  Australia's Dean Gardiner won the kayak race and Pat Erwin of Kailua, Oahu,  won the solo canoe race in a time of 4:23:24.
  
  
• 1994 ~ 74 Entrants Finished
  The men's and women's surfski times were smashed.  Gardiner crossed in 3:24:08 and Hawaii's Kelly Fey broke Hall's record with a time of 4:12:34.
  
  
• 1995 ~ After battling one another across the Channel, brothers Oscar and Herman Chalupsky conferred shortly before the finish and decided to cross together.  A tie was declared as the two held onto one another's surfski to cross the line.  Kelly Fey kept the women's title and Kauai's Steve Cole won the outrigger canoe division.
  
  
• 1996 ~ Dean Gardiner led the kayak competition, winning his fourth race in five years with a time of 3:38:27. Followed by fellow Aussies Brad Kane and Martin Kenny, second and third place respectively, the Australian team easily captured the international team title.  Nalu Kukea, son of the late Kala Kukea, was the first Hawaii finisher and 4th overall.  In the solo canoe division, Mark Rigg triumphed in his first solo crossing with a time of 4:17:35, beating out 1994 winner Pat Erwin (4:25:15).  In the women's open division, Sonia Lambert and Loretta Toth became the first women ever to cross the Kaiwi Channel in a solo canoe. Lambert won the race with a time of (5:30:35)
  
  
• 1997 ~ Three-peat / four new records ~ Dean Gardiner continued his winning streak, finishing in a time of (3:21:26) Kelly Fey held onto her title with a time of( 4:02:47), as did solo canoeist Mark Rigg with a time of 4:14:52. In her first solo Molokai crossing, Donna Kahakui captured first place and a new record (5:16:29)
  
  
• 1998 ~ Dean Gardiner repeated his 1997 men's kayak victory in a time of 3:27:15, edging out Nalu Kukea who finished less than a minute later with a time of 3:28:09.  Gardiner was also part of the first place international team competition, a race-within-a-race, along with Australian team mates Martin Kenny and Brad Kane.
The solo canoe battle between Mark Rigg and John Foti continued throughout the crossing of the Channel, with Rigg finishing first for the third consecutive year with a new record at that time, of 4:06:22, just one minute, two seconds ahead of John Foti (4:07:24) Kelly Fey continued her reign as the first female kayaker to cross, with a time of 4:09:53, followed by Nicole Montel of Tahiti with a time of 4:21:05.  In her first solo canoe crossing, Cheryl Villegas from the Big Island of Hawaii captured the first place women's solo canoe title with a time of 5:21:10.  Last year's champion, Donna Kahakui, finished second this year with a 5:31:08.


• 1999 ~ 99 Entrants Finished
Once again, Dean Gardiner continued his winning streak finishing with a time of 3:37:05 while 18 year old Karel Tresnak Jr. had a six minute lead on Mark Rigg in the OC-1 division with a time of 4:17:05


• 2000 ~ 77 Entrants Finished
~ Oscar Chalupsky came across the finish line with a time of 3:21:48. Karel Tresnak Jr. repeated his second win with a time of 3:49:19


• 2001 ~ 75 Entrants Finished
Dean Gardiner edged out Lewis Laughlin in less than two minutes with a time of 3:35:57. Karel Tresnak Jr. did it again by winning his third consecutive win with a time of 3:52:09. Mike Judd was close behind with a time of 3:54:35.


• 2002 ~ 79 Entrants Finished
  OC-1 Kai Bartlett had a great run at 3:42:37 while Mike Judd came in at a 3:47:09. Kealii Paiaina took third with a 3:51:45.
  Australia takes first, second and third place. Dean Gardiner of Australia did it again with a better time than last year of 3:24:52. Martin Kenny of Australia was behind him for a second place finish of 3:27:24. Grant Kenny was right behind his Brother for a third place finish of 3:30:27
  
  
• 2003 ~ 81 Entrants Finished
  OC-1 Karel Tresnak Jr. is back with a first place win of 3:51:32 just ahead of Kai Bartlett with a second place finish of 3:52:57. Mike Judd came in with the third place finish of 3:56:51.
  Oscar Chalupsky came in first place with a time of 3:28:33
  
  
• 2004 ~ 100 Entrants Finished
  Herman Chalupsky is the first Surfski to cross the finish line with a time of 3:48:40, Dave Kissane came in second with a 3:55:16 and Oscar Chalupsky third with a 3:58:10
  OC-1 Karel Tresnak Jr. was back in play with a first place time of 4:11:15 with Mike Judd taking second with a 4:13:32 and a young Danny Ching with a third place finish of 4:22:23.
  
  
• 2005 ~ 115 Entrants Finished
  Oscar Chalupsky takes first place in the Surfski with a time of 3:28:38. Nathan Baggaley comes in second place with a great time of 3:30:52 and Dean Gardiner takes a close third with a 3:31:45
  OC-1 Kai Bartlett comes in first place with a time of 3:52:37. Mike Judd takes second with a 3:57:45 and in third place is Manny Kulukulualani with a 3:59:13.

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