Why the Chicago Yacht Club Race to Mackinac remains one of sailing’s most storied competitions

Chicago Yacht Club Race to Mackinac
Sailboats sit on the waters of Lake Michigan, just beyond the clubhouse of the Chicago Yacht Club’s Monroe location. The organization hosts the Chicago Yacht Club Race to Mackinac, which in 2022 will record its 113th year. (Alyssa Haduck/Medill Reports)

By Alyssa Haduck
Medill Reports

The Chicago Yacht Club Race to Mackinac is anything but normal. 

After 112 years, the July competition remains the world’s longest freshwater sailboat race, with participants trekking 333 miles, or 289.4 nautical miles, from Chicago’s Navy Pier to Mackinac Island, Michigan. But that’s where the consistency ceases.

“You’re going to the same place,” sailor Sam Veilleux said, “but something different happens every time.”

While Lake Michigan’s ever-changing atmosphere makes the race impossible to predict, race organizers and sailing crews are currently doing what they can to prepare. Veilleux, who also serves as the race chair, is leading a team of 20 volunteers — along with the staff at the Chicago Yacht Club — in identifying officials, organizing incoming entries and finalizing event contracts. 

The race generally attracts more than 300 boats crewed by more than 3,000 participants ranging from serious sailors to leisure boaters, but this year’s race is already on pace to become one of the largest in recent history, Veilleux said. He suspects the pandemic has driven an increase in interest in the event, which was canceled in 2020 due to COVID-19 restrictions.

The contest’s fastest recorded time is just under 24 hours, but it can take up to three days for crews, no matter their skill level, to complete the race — an experience Veilleux knows all too well.

“There are challenges, there are storms, but probably more frustrating than that is sitting there with no wind, swatting flies and eating warm sandwiches,” he said. “It’s not just a physical challenge, it’s a mental challenge.”

Despite these struggles, competitors keep coming back for more. 

“I’ve done this race six times, but I’m on the low end of the spectrum,” he said. “Some of the guys that I’ve raced with have done it 40 times.”

One such sailor is Angela Graham, who has participated in 33 Mackinac races. She began competing at a time that preceded today’s technology, remembering when race participants would line up at a payphone after days on the lake to call home and report their results. 

But Graham’s extensive experience has earned her a place in the Race to Mackinac hall of fame: the Island Goat Sailing Society. In fact, Graham is commodore, or president, of the club that serves to celebrate those who have sailed in at least 25 Mackinac races. 

While the moniker may suggest the Island Goats are so named for their greatest-of-all-time status, the label actually harkens back to early sailors’ odorous similarity to these animals. 

The organization was founded by three sailors in 1959 and has grown to more than 350 active members and 500 all-time. While these race participants have each encountered their fair share of weather woes, Graham said competitors have endured particularly brutal conditions in recent years.

“There’s almost always a point where you’d rather be someplace else,” she said.

Few understand Lake Michigan’s climate better than Chris Bedford, who has been studying the lake’s weather patterns for decades as a meteorologist specializing in competitive sailing. Bedford has been the Race to Mackinac weather coach for nearly 20 years, providing generic forecasts to all teams and tailored recommendations to clients who must become their own meteorologists once out in the unpredictable waters of Lake Michigan.

“The cool thing about this race, in my opinion, is it has elements of both a local coastal race and an offshore ocean race,” Bedford said, referencing Lake Michigan’s unique size and shape. “They’re two different problems from a weather forecasting standpoint, but in this case, they’re both happening at the same time.”

Even with its chaos, the lake hosts some of the race’s most awe-inspiring moments, connecting competitors with the elements like little else can. These memories motivate sailors like Graham to return year after year. 

“Being out in the middle of the lake and seeing the stars at night, or getting close to the island and smelling the pine trees, there’s just something about that,” she said.

And while Veilleux still faces weeks of coordination ahead, both as race chair and as a crew member, he puts in his hours on land looking forward to the promise of peace on the lake.

“You see the sun come up in the morning, the smell of coffee brewing — it’s great to get away from it all,” he said.


Alyssa Haduck is a sports media graduate student at Medill. You can follow her on Twitter at @Alyssa_Haduck.