Race History

Chicago Yacht Club's most famous event is the Chicago Yacht Club Race to Mackinac, which is the longest annual freshwater sailing race in the world.

Starting in 1898 with a mere five boats, The Mac has evolved into a world-class sporting event. After the first race in 1898, the Race to Mackinac was not held for five years until the second race in 1904. By 1906, the race had developed a healthy following and, in that year, the original Mackinac trophy was purchased. The race has seen occasional sustained violent weather in the blows of 1911, 1937 and 1970. After gale force winds took down most of the fleet in the Mac of 1911, the finish in the 1912 and 1913 races was changed to Harbor Springs on Little Traverse Bay instead of Mackinac Island. Race organizers felt the shorter distance was safer. From 1914 until 1916 the Mac was back to its full distance until WWI. From 1917-1920 there were no Mac races due to the strains of the War, which took away yachtsmen and put many boats out of commission. Since 1921, the Race to Mackinac has run consecutively every year, remains the longest annual freshwater distance race, and is recognized as one of the most prestigious sailing races in the world.

Today, sailors from Maine to California make this race an invariable part of their summer. Moreover, each year the Mac hosts sailors from as far off as Hong Kong, New Zealand and Australia. Although the Mac remains primarily an amateur event, this race has a proven track record of attracting some of the finest sailing talent in the sport. The monohull record of 23 hours, 30 minutes, and 34 seconds set by Roy Disney’s Pyewacket in 2002, and Steve Fossett on Stars and Stripes set the multihull record of 18 hours, 50 minutes, and 32 seconds in 1998. Both records still stand today. The unpredictable weather and fickle winds on Lake Michigan make the Race to Mackinac a supreme test, which many competitors feel rivals any ocean race. As one veteran sailor put it, "It’s fun, but it’s serious fun."

2008 marked the 110th anniversary of the first race, and the 100th time sailors raced 333 miles from Chicago to Mackinac Island. Although there have been changes to the race over the years, the basic elements of this venerable contest have remained unchanged for over 100 years. Stripped down to its essence, The Mac, like all sailboat racing, is still primarily a test of strength, endurance, strategy and willpower. And let’s not forget the dearest friend (and most menacing foe) of all sailors-- the wind. 

The First Mac 

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.