Mackinac Island Events: Every July, crowds assemble at the Mackinac Island Harbor to watch them come in. Small white smears in the dark blue distance—like a flock of grounded seagulls, the over three hundred sail boats have battled their way up the Mitten Coast to Mackinac Island. Now one of the most famous events in competitive sailing, the world’s longest freshwater sail boat race got it’s start as a bet between two 19th century Chicago sailors.

In 1886, the Racine Boat Manufacturing Company began work on the newly designed fin-keep sloops-one masted sail boats designed to have less drag in the water, and therefore move much faster than their full bellied counterparts. The first two boats were named the Siren, owned by George Peate, and the Vanenna, owned by W.R. Crawford. For years, the Chicago sailing community speculated which sloop would be faster.

The boats were finally ready to settle the question in 1896 to disappointing results. The first year, they raced from Chicago to Michigan City, but the Siren protested the Vanenna’s victory, claiming to be at an unfair disadvantage with “old sails.”  The second race, this time to Milwaukee, was never finished due to heavy fog which caused the sloops to sail off course. In 1898 George Peate and W.R. Crawford determined to set the record straight once and for all. The Chicago Yacht Club announced a three day regatta for June 4,11 and 18. Bets rode high, and the air was thick with boasts and brags. To the disappointment of the Siren’s crew, the Vanenna remained undefeated.

But that didn’t stop the Siren from re-grouping and challenging their sister ship one last time in 1898. Peate and the Siren needed a dramatic win that would silence any questions of the Vanenna’s supposed superiority- they needed to beat them in a race to Mackinac Island.  The course would be  long and difficult but the rewards of the luxurious summer town of Mackinac Island waited at the end. It would be the ultimate match- a 333 mile long race battling the winds, rocky harbors, and unpredictable weather of Lake Michigan. And so the Siren and the Vanenna, accompanied by three schooners the Hawthorne, Toxteth, and Nomad, set off from the Chicago Yacht Club for Mackinac Island.

Pride was damaged and money lost at the end of that race. For the fourth time the Vanenna trounced the Siren, coming into port at Mackinac Island in 52 hours, 17 minutes, and 50 seconds. To add insult to injury, the Siren finished less than forty five minutes later.

Today, the Chicago Yacht Club Race to Mackinac follows more or less the same path as the two sister sloops. The race has been run consecutively since 1921, and this year over 300 boats will be racing, with participants coming from both coasts of the United States, and places like Hong Kong and New Zealand! Follow your favorite boats (look for a list of Northern Michigan sailors later!) online, thanks to GPS tracking devices. Sailors have made making it to Mackinac a victory in and of itself, rife with tradition. It is well worth the trip to the Island to see them celebrating in the harbor.

Despite modern updates, the spirit of the race remains unchanged. As the Chicago Yacht Club says, “stripped down to it’s essence, the Mac, like all sail boat races, is still primarily a test of strength, endurance, and willpower.”

Learn more about the Race to Mackinac at