Little did Joseph Myers know that when he designed the fin-keel sloops (Siren 59'6" and the Vanenna 64') it would start into motion the beginning of the world's most famous and longest freshwater sailing race. From the start of their construction by the Racine Boat Manufacturing Company in 1886, there was ample talk of which vessel would be the fastest.
Although the races began in 1896, the race outcomes were not conclusive. The first race to Michigan City was disputed when Vanenna claimed the race and Siren protested because she had old sails that were inadequate for the race. To this day, the second race to Milwaukee is still in dispute, for the fog caused both sloops to sail off course and thus started the question, "did the race ever finish?"
A couple of years passed until the 1898 announcement for a series of three races sponsored by the Chicago Yacht Club. Owners George Peate of Siren and W.R. Crawford of Vanenna set out to make the record straight. They agreed to a three day regatta on June 4th, 11th and 18th. Both owners engaged in much boosting and betting, and they were prepared to spend whatever it took to be ready.
Behind this backdrop was the hangover from the loss of the Fisher Cup of 1883 between Chicago's Cora and the Canada's Atlanta. This loss began a declining effect on memberships to the Chicago yachting community for close to 15 years. By 1897, there were only six members and two yachts representing the Chicago Yacht Club. A strong drive for membership in 1898 increased this number rapidly to sixty members and sixteen yachts, thus laying the groundwork for creating new excitement and an era of racing at the Chicago Yacht Club.
After three races in June of 1898, Vanenna remained undefeated and the discussion emerged to have a very unique and challenging race. In 1897, the New York Yacht Club sponsored a long distance race attracting vessels of larger sizes. The Chicago Yacht Club saw an opportunity to create its own attraction for larger vessels and renew the sport of sailing for the Chicago sailing community. Mackinac Island was a destination that was favored by many sailors by taking a multi-port route up Lake Michigan. Many Chicago Yacht Club members throughout history had houses or stayed on the island for vacations. These members conceived of a race that would challenge every sailor to the weather, winds, storms, and seas, as well as the big question: What course do you take on a 333 mile race?
And so began the first Mac Race with two sloops, Siren and Vanenna and three schooners, Hawthorne, Toxteth and Nomad. The excitement was immediate and the wagers and posturing began. Once again, Siren and Vanenna would dance with each other on the Great Lakes.
After 52 hours 17 minutes and 50 seconds - Vanenna claimed her place in history as the first winner of the Race to Mackinac Island. Siren placed second, 37 minutes and 20 seconds behind her nemesis, but beat the schooner Hawthorne by 45 minutes.