“The Meeting at the King’s Boat House (October 19, 1885) – The meeting was called to order (and a) motion was passed that an association be formed to be called “The Hawaiian Rowing and Yachting Association.’”
“The association was to be represented by three delegates each from the Myrtle, Honolulu, and Kapiolani Clubs, and by one delegate each from all other established clubs. A committee of one from each club was appointed to make by-laws and racing rules.” (Daily Honolulu Press, October 20, 1885)
“A special meeting of the Hawaiian Yachting and Rowing Association was held last evening at the Iolani Boat Club House … After routine business had been transacted the following resolution was put and carried;”
“Resolved that the Association do hereby appropriate the sum of $350 for the express purpose of purchasing a silver cup to be sailed for annually up on the 4th of July under the auspices and conditions of the Hawaiian Yachting and Rowing Association by first class yachts of dimensions not to exceed 40 feet over all, said cup to be called the ‘Hawaiian Challenge Cup.’” (Daily Bulletin, June 19, 1889)
“The Challenge Cup, which is a very handsome one of solid silver and old silver finish in the form of a Japanese vase, is lettered on one side with the name of the Association, while the other side has a splendid view of Diamond Head with two yachts running seaward.”
“It is embellished with birds, fishes, seaweed and marine emblems. It is a perpetual challenge cup, and Messrs. Iaukea, Hatch and Cecil Brown, the owners of the Healani, hold it for one year. A pennant is given to the winner each year. The one this year is of a white silk ground with the monogram HRYA in blue letters, surmounted by a crown.” (Daily Bulletin, December 2, 1889)
“The cup is an ornate affair, etched on one side with the title of the trophy and on the other with a view of Diamond Head and racing yachts. On the shoulders cunningly wrought objects typical of the sport are attached. The names of previous winners are engraved on the cup.” (Sunday Advertiser, September 6, 1903)
“The Hawaiian Challenge Cup is an elegant silver trophy valued at $400. It was presented a number of years ago by the Hawaiian Rowing and Yachting Association, now defunct, and was to be raced for not oftener than once every year.” (Sunday Advertiser, September 6, 1903)
“Among boats that have won the cup are the Healani, Helene and Bonnie Dundee, the latter of which held it from 1893 until last year, on which occasion the Eva won.” (Pacific Commercial Advertiser, August 1, 1899)
“The Hawaiian Challenge Cup is open to all yachts over five and not exceeding ten tons measurement, this limitation not applying to yachts which were in Hawaiian waters and entered for the race previous to July 4th, 1899.”
“The course set runs from Waikiki to Pearl Harbor and back, finishing off the Oceanic wharf, making a course of twenty-three miles.”
“The cup was originally donated by the Hawaiian Rowing and Yachting Association, the conditions under which it was sailed being drawn up at a meeting of the Association in the ʻIolani Boat Club hall on June 28, 1889.” (Sunday Advertiser, September 6, 1903)
“An important event in the yachting annals of the islands took place on Saturday afternoon at the boathouse of His Majesty the King. It was the presentation of the silver challenge cup and a handsome pennant won by the yacht Healani on the 4th of July.”
“His Majesty, as president of the Hawaiian Rowing and Yachting Association, and who has always done so much in stimulating yachting and rowing in the islands as asked to make the presentation, and gracefully acceded to the request.”
“An elegant lunch was provided by His Majesty, and on the table, which was nicely decorated with flowers, stood the challenge cup. After ample justice had been done the good things His Majesty rose and said:”
“Representatives of the Hawaiian Yachting and Rowing Association and Gentlemen: At a special meeting of this Association held on the 18th of June last, it was resolved that a sum be appropriated for the express purpose of purchasing a silver cup, to be sailed for annually on the 4th of July, said cup to be called the ‘Hawaiian Challenge Cup.’”
“Subsequently a Pennant was added, and the prize then was the “Hawaiian Challenge Cup and Pennant for 1889.” The first race under the new conditions was sailed on the 4th of July. Five yachts I think started, the race was won by the Healani, being closely followed by the second boat.”
“Gentlemen, you are present on this occasion to witness the presentation of the above prize and pennant to the owners of the winning yacht. Messrs. Iaukea, Hatch, and Brown : As President of, and on behalf of the Hawaiian Yachting and Rowing Association, I take pleasure in handing over to you this handsome souvenir of an enjoyable day’s sport, and a well-contested trophy.”
“Hon. CP Iaukea, one of the owners of the yacht Healani, in receiving the challenge cup said: Your Majesty and Gentlemen, in receiving this trophy from Your Majesty’s hands, permit me on behalf of the owners of the yacht Healani, to express my great pleasure and satisfaction in now bearing away the palm during the first year of its competition.”
“It must also be highly gratifying to Your Majesty that the Healani, with which Your Majesty has so long been associated, should have successfully competed for the cup. The great interest which Your Majesty has for many years shown in yachting has no doubt animated others to a like appreciation of this healthy and instructive sport, as evidenced by the number of splendid yachts now adorning our bay.”
“In thanking Your Majesty for the honor conferred, permit me to express the hope that Your Majesty may continue to assist lovers of yachting with your gracious patronage. With Your Majesty’s permission I shall ask the gentlemen present to join me in wishing you, our royal President of HYR Association, a very good health.”
“His Majesty’s health was drunk by all standing, after which social conversation, principally on yachting matters, was indulged in for a time.” (Daily Bulletin, December 2, 1889)
“From this time the cup lay fallow for seven years until the advent of the ‘Gladys’ into our waters. A race was then sailed between the ‘Bonnie Dundee’ (now ‘Mary L’), and the Gladys on September 13, 1899, when the Gladys won by 23 minutes or one minute to the mile. Governor Dole sailed the Bonnie Dundee and T. W. Hobron the Gladys.” (Sunday Advertiser, September 6, 1903)
Reportedly, over the years, the prize became known as the ‘Kalākaua Cup.’ There were a few periods of inactivity due to disinterest and extenuating circumstances, as well as the disappearance of the cup itself.
When Castle & Cooke was moving offices, their old vault was opened and the trophy appeared it was filled with silverware belonging to the last winner, Tom Hobron, in the yacht ‘Gladys Mary’ in 1911.
The last winner of the Hawaiian Challenge Trophy was the Star class yacht ‘Roulette,’ skippered by Laurie S Dowsett, the 17-year-old son of HM Dowsett, with his crew Lloyd B. Osborne. This was the summer of 1941. Names of winning yachts and skipper/crew from 1925 through 1941 are inscribed on the trophy. (Waikiki Yacht Club)
The trophy was re-dedicated in 1986 and today is awarded annually to the winner of the Fourth of July Regatta consisting of three separate races. The first race is from Waikiki to Kaneohe, the second is an offshore race in the waters off of Kaneohe Bay, and the third is a race from Kaneohe to Waikiki. (Stowell)
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