Sailing The Mac


If you’re like most people, the American Midwest is not the first place that pops to mind when you think of sailing. But from the skyscraper canyons of Chicago to the rolling farmland of Wisconsin, hundreds of fanatical heartland sailors as well as those from around the United States and overseas anxiously await the Chicago to Mackinac race on Lake Michigan, held every year in July.

Known as the “Mac”, the 333-mile race from Chicago to Mackinac Island is the world’s longest freshwater race on the planet’s third largest fresh water lake. It’s always been near and dear to our hearts at Lands’ End, since we got our start as a sailing hardware business in Chicago in 1963, and have sailed the Mac ourselves many times. (Admittedly, often as “rail meat,” a crew member who sits on the rail most of the race, using his or her weight to help keep the boat flat or induce heel in light air.)

“Sailing in Lake Michigan is not like sailing in a mill pond,” says Randy Adolphs, a long-time sailing buddy of our company founder Gary Comer. Randy has sailed the Mac four times, and has two transatlantic crossings under his belt as well as sails across the Red Sea, the Mediterranean and a run from the Galapagos to Easter Island. He knows first hand the punches that Lake Michigan can throw. “It’s very comparable to ocean racing,” he says. “I remember one year Ted Turner entered in a boat called American Eagle. It blew 40 to 50 miles per hour. Needless to say, Ted was impressed.”

No kidding. That was back in 1970, and it was one of the most treacherous Macs since the first race in 1898. The 13-foot seas battered the 167 boats and crippled 88 of them—broken masts, wrecked gear, ripped sails, injuries and fatigue took their toll on the most famous race in the middle of America.

In the Hard Blow of 1937, only eight yachts out of 42 made it to the finish at the Round Island Lighthouse off Mackinac Island. Of course, Mother Nature can throw curve balls in the other direction, as well. Last year was one of the most lethargic Mac races on record, with so little wind that “half the fleet didn’t arrive by the Tuesday afternoon awards ceremony,” says Rick Lillie, chairman of the Mackinac committee and a member of the Chicago Yacht Club since 1989. In case you were wondering, the current uncorrected course record—before handicapping for vessel size—is held by Roy Disney (Walt’s brother) aboard Pyewacket. His time? 23 hours, 30 minutes and 24 seconds.

“The longer the race the shorter the boat becomes,” says Lillie, “and many are happy to get off of it.”

Fortunately for Mac sailors there is the Pink Pony bar located within convenient stumbing distance of the wharf. “Sailing is a sport that involves a fair amount of bragging and storytelling,” says Lillie, “and during the first beer the waves on the voyage were two feet. By the fifth or sixth beer, they become eight feet.”

What happens if sailors arrive in the wee hours of the morning and the Pink Pony is shuttered up? Lillie says most sailors are prepared for such a dreadful emergency: “On board we carry a short supply of what we refer to as an ‘arrival beverage,’ which is usually Mount Gay Rum.”

Of course, he adds, “we keep it under lock and key.”

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