Outrigger Canoe Club began sponsoring a new long distance race, named for Skippy Kamakawiwoole, in 1985 with Kilakila o Hawaii, a new canoe club located at Pokai Bay. Skippy was a well-known Hawaiian entertainer from the Leeward Coast who passed away in 1982. The race was open to all clubs. The men’s race began outside the OCC at the channel entrance, and ended at Pokai Bay, a distance of approximately 31 miles. After the men’s race, an iron women’s crew padded six miles from Pokai Bay to Makaha and Maili and returned to Pokai Bay.
The race had two unique distinctions. The race had a Le Mans start with all but one paddler in the water when the starting gun went off. The second distinction was that each boat carried a fish all the way to the finish at Pokai Bay and a paddler had to jump out of the boat and run with it to the judges on the beach.
In 1987, OHCRA began a women’s distance race they called E Lauhoe Na Wahine. It was scheduled two weeks prior to the Na Wahine O Ke Kai. It was over the same course as the Skippy. Thereafter the women no longer competed in the Skippy.
The Skippy race course changed several times during the years. In 1990 the race was from Maunalua Bay to Paradise Cove. In 1992, it started again at the Outrigger and finished at Pokai Bay. In 1994 the race course was changed from Maunalua Bay to Nimitz Beach, a distance of 28 miles. In 1996 it changed again from Maunalua Bay to Pokai Bay. In 1997, it was Maunalua Bay to Nanakuli Beach Park. In 2000, it changed to its current course, Maunalua Bay to Ko Olina.
The year 2001 was the last year of the Outrigger’s sponsorship of the Skippy Kamakawiwoole race. In 2002, following the untimely death of OCC’s beloved waterman Henry Ayau, the race was renamed the Henry Ayau Men’s International Canoe Race, and was sponsored by Steinlager. The course remained from Maunalua Bay to Ko Olina. The race is the last race for men before the Molokai Ho’e, traditionally held on the second Sunday of October. Today, the race is sponsored by the Oahu Hawaiian Canoe Racing Association.