2025 Chicago to Mackinac Race

Chicago to Mac Sailing Race at Mackinac Island by Stephen R. Cloutier

Chicago to Mac Sailing Race at Mackinac Island by Stephen R. Cloutier

The Chicago Yacht Club Race To Mackinac starts Friday morning (July 18). The Chicago to Mac is the longest annual freshwater sailing race in the world, spanning 333 statute miles from the start at the Chicago Yacht Club, up the western shore of Lake Michigan, passing under the Mackinac Bridge to finish at Mackinac Island. They explain that:

…the race’s unpredictable weather and shifting winds on Lake Michigan make it a supreme test of sailing skill, rivaling many offshore ocean races. What first began in 1898 with just five boats has now evolved into a world-class sporting event. The origins of the Race to Mackinac date back to 1898, when Joseph Myers designed two fin-keel sloops, Siren and Vanenna. These vessels sparked a competition between their owners, George Peate of Siren and W.R. Crawford of Vanenna, and after three races in June of 1898, Vanenna remained undefeated. This prompted the idea of a unique, challenging race – one that would forever change the history of sailing.

Lots more on the Race to Mackinac website. If you click the pic above, you can see more of Stephen’s photos. For sure follow him on Instagram for his latest! Also more about Round Island lighthouse on Michigan in Pictures!

Chicago to Mac at Mackinac Bridge by Stephen R. Cloutier

Chicago to Mac at Mackinac Bridge by Stephen R. Cloutier

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2017 Chicago to Mackinac Sailing Race

Absolute Chicago-Mackinac, photo by Jim Sorbie

When I wandered down to Fishtown in Leland yesterday afternoon, the number one topic of conversation was the annual Chicago to Mackinac sailing race. The 333-mile race from Chicago’s Navy Pier to Mackinac Island is kind of a big deal in communities along Michigan’s western coast like mine. I almost always know a couple of people who are racing, and after the race gets underway, you’ll hear a lot of speculation about the time that the boats will enter the Manitou Passage and then what time they’ll finish at Mackinac Island.

One of the things that’s particularly cool to me is that the Chicago to Mac is one of the few events that ties the whole community to the weather and condition of Lake Michigan. People will take boats out to watch them, or climb Pyramid Point or Whaleback for a view of the boats if they stream past when it’s light out. If you’re within distance of a community like Leland, Frankfort, Ludington, Elk Rapids or up near the Mackinac Bridge, consider checking out likely times boats will pass, grab the binoculars and see if you can get a glimpse of the racers.

Jim writes: Summer Flashback – We’re trying desperately to pass an old friend on the run in to the Island – no luck!

View his photo from near the end of the 2013 race photo background bigtacular and see more in his Mac Races (Chicago & Port Huron) slideshow.

PS: Definitely check out their 2016 Race Photo Contest winning photo!