The Molokai Challenge, recognized as the World Surf Ski and OC1 Championship, is the title watermen covet most. The solo race begins near the west end of the island of Molokai, crosses the volatile Ka’iwi Channel — considered one of the roughest ocean channels in the world – and finishes on Waikiki’s Queens Beach which is on Oahu for the first time in 2007. The new distance is 32.3 nautical miles.

Win the greatest ocean race in the world and you’re in select company. Over the past 25 years, only six men have won the surf ski division: Grant Kenny, the famed Aussie Ocean Ironman and Olympic Bronze medalist, won his first of five titles in 1979. In 1983, a 20-year-old South African named Oscar Chalupsky defeated Kenny to win the first of his seven consecutive titles. When Chalupsky was barred from international competition for five years due to apartheid, Australia’s Dean Gardiner stepped in as the Molo man to beat, winning his first title in 1993. A former commercial fisherman from Perth, Gardiner holds the course record of 3:21:26 set in 1997. Herman Chalupsky, Oscar’s younger brother, is the only other ski paddler to win the race more than once.

In 2003, Oscar and Dean, tied at nine titles each, staged a classic duel to become the first man to 10. With a world class field that included Grant and Martin Kenny, Olympian Clint Robinson, Tahitian Lewis Laughlin, Herman Chalupsky, and Gold medalist Greg Barton, Oscar only caught Gardiner along Oahu’s Chinaman’s Wall for the record win. He added his record 11th title in 2004.

Oahu native Pat Erwin won the first solo canoe race across the channel in 1993. After finishing 10th in his first solo Molokai in 1998, 18-year-old high school senior Karel Tresnak Jr. gave himself a nearly unimaginable graduation present, beating three-time defending champion Mark Rigg, a former All-America volleyball player and a legend in the sport. In 2000, Tresnak became the first OC1 paddler to crack four hours. His time of 3:49:19 was eight minutes better than John Foti. In 2006, a year after breaking the nose off his boat, Tresnak won his record sixth solo title in a record time of 3:42:37.


The 2007 race is the 31st 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. Here are some of the highlights of the race.

  • 1976 ~ Adams paddled for 7 hours, 30 minutes in his first effort. He repeated the crossing a year later with two others, including Dean Hayward, a coach at Kamehameha Schools, who won in a time of 6 hours, 45 minutes.
  • 1978 ~ Kalai Handley of Oahu, won the race and since that time no other male competitor from Hawaii has finished first in the surf ski division. Marshall Rosa finished 2nd eight times behind Oscar Chalupsky and remains a formidable competitor late in his 50s.
  • 1979 ~ Eighteen paddlers made the crossing, including the first international competitor Grant Kenny of Australia, who won in 5:37:05.
  • 1980 ~ Eve Anderson became the first female competitor.
  • 1983 ~ South African Oscar Chalupsky won his first ski title, defeating Grant Kenny.
  • 1989 ~ Oscar Chalupsky posted his 7th straight victory with a time of 3:39:47.
  • 1990 ~ Grant Kenny returned to the winners circle, crossing the channel in 3:44:45, his fourth win. Tahiti-born Lesline Conner of Oahu won the women’s race for her fourth time.
  • 1993 ~ Three-time women’s winner, Jane Hall, from Sydney, Australia, set a women’s record in a time of 4:14:23. 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 ~ A record year: Gardiner crossed in 3:24:08 and Hawaii’s Kelly Fey broke Hall’s record with a time of 4:12:34.
  • 1995 ~ After dueling side-by-side across the Channel, brothers Oscar and Herman Chalupsky decided to cross together — the only tie in race history. Kelly Fey repeated as women’s champ and Kauai’s Steve Cole won the outrigger canoe division.
  • 1996 ~ Dean Gardiner won his fourth race in five years with a time of 3:38:27 followed by fellow Aussies Brad Kane and Martin Kenny. Nalu Kukea was the first Hawaii finisher and 4th overall. In the solo canoe division, Mark Rigg won in his first solo crossing with a time of 4:17:35, beating 1994 winner Pat Erwin. In the women’s 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 ~ Dean Gardiner continued his winning streak, finishing in a record time of (3:21:26) that still stands. Kelly Fey retained her title in a record 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 as men’s kayak champion in a time of 3:27:15, edging out Nalu Kukea (3:28:09). The solo canoe battle featured Mark Rigg and John Foti with Rigg finishing first for the third consecutive year with a new record of 4:06:22. Kelly Fey continued her reign as the first female kayaker to cross, with a time of 4:09:53. In her first solo canoe crossing; Cheryl Villegas from the Big Island of Hawaii won her first women’s solo canoe title with a time of 5:21:10.
  • 1999 ~ Dean Gardiner continued his win streak, finishing with a time of 3:37:05 while 18-year-old Karel Tresnak Jr. downed Mark Rigg in the OC-1 division for his first win with a time of 4:17:05
  • 2000 ~ Oscar Chalupsky won his ninth title with a time of 3:21:48. Karel Tresnak Jr. repeated his second win with a time of 3:49:19
  • 2001 ~ 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 second with a time of 3:54:35.
  • 2002 ~ 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. Dean Gardiner did it again, winning with a time of 3:24:52. Martin Kenny of Australia was second in 3:27:24. Grant Kenny was third.
  • 2003 ~ OC-1 Karel Tresnak Jr. won his fourth title (3:51:32), edging Kai Bartlett (3:52:57). Mike Judd was third place finish of 3:56:51. Oscar Chalupsky (3:28.33) edged Dean Gardiner to become the first to win 10 titles.
  • 2004 ~ Herman Chalupsky crushed the field with a time of 3:48:40; Aussie 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 Danny Ching with a third place finish of 4:22:23.
  • 2005 ~ Oscar Chalupsky wins his 11th Ski title with a time of 3:28:38. Australian double Silver medalist Nathan Baggaley finishes a close second place in 3:30:52 and Dean Gardiner 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. 
  • 2006 ~ First time entrant Clint Pretorius, a 21-year-old from Durban, South Africa, makes a late break from Oscar Chalupsky and Aussie Gold and Silver medalist Clint Robinson for the win, breaking the Gardiner/Chalupsky stranglehold on the ski side. Pretorious’ time of 3:22.14 was just 40 seconds off Gardiner’s course record. Sixth overall, Mark Sandvold was the first Hawaiian finisher. The female winner was Maggie Twigg-Smith (4:27:05) with Deanne Hemmens second (4:47:08). In the OC1, Tresnak Jr. won his record-sixth title (3:42:24) with Kai Bartlett and California’s Danny Ching third. Dane Ward won the women’s OC1 division with a time of 4:49:15.


The race boasts an admirable safety record. In the three decades paddlers have been crossing the channel there has never been an accident. Probably the most serious condition experienced by any entrant has been mild sunburn, some dehydration and – after 32 miles of non-stop paddling – fatigue.

Nevertheless because of the rough conditions and difficulty of the race, participants are screened for their level of paddling skill. Safety rules require each paddler to be accompanied by an escort boat during the crossing and new ways of tracking the paddlers are being researched to increase the safety of the race.

A list of escort boats is being prepared and if you are in need of a boat for the race, please contact us via the contact page.