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Hoist the main and trim the jib: It’s the 105th Chicago Yacht Club Race to Mackinac!

Yachts leaving the city at the Chicago Yacht Club Race to Mackniac

Here is the beauty of the Mac, aside from it being the world’s oldest annual freshwater race: The record finish time set in 1911 wasn’t broken until 1987. The very first Chicago to Mackinac race was held in 1898 when five sailboats—Vanenna, Siren, Hawthorne, Toxteth and Nomad—zigzagged their way up the lake to the small island that sits where Lake Michigan flows into Lake Huron. Vanenna won it that year, in about 52 hours.

In 1911 Amorita won the race in a little over 31 hours, and that record stood until Pied Piper bested it by more than five hours in 1987. Therein lies the beauty of the race, which is set to begin July 13 this summer.

Regardless of advances in technology—carbon fiber masts replacing wooden poles, nylon spinnakers and carbon jibs replacing drapey canvas—there will always be weather. There will always be personnel issues, too, because wind is not the only thing that makes a sailboat go. It takes people.

Mark Landwer, 43, sailed in his first Race to Mackinac at age 9, getting seasick on the way to the starting line. He skipped the race the next year but was back at the starting line at age 11 and has not missed a Mac race since. At age 34 he became the youngest sailor ever inducted into the Island Goats Sailing Society, the exclusive club for veterans of 25 Chicago Mackinac Races. The term “Old Goat” is derived from the distinctive odor sailors emit after the long maritime journey from Chicago to northern Michigan.

Boats from coast to coast compete in the Mac, along with several from Canada and spots across the world—as far away as Hong Kong, Australia and New Zealand. It sees its fair share of 70- and 80-footers, but most boats fall in the 35- to 45-foot range. Last year it hosted 344 boats and about 3,500 sailors—including a cruising division, which was added in 2007, pushing the boat tally up past 300.

That’s about the only thing a Mac racer can count on these days—that there will be at least 3,000 other sailors and 300 boats. The weather, the thing that makes the Mac possible, is as unpredictable in the middle of the lake as it is in the middle of the Loop. One day a sailor can sit through suffering calm, boats bobbing like corks on glassy water, and the next day he can be securing his harness to the deck to keep himself on the boat and out of the towering, relentless waves. That yacht that looked so vast dockside in Monroe Harbor can suddenly appear awfully small in certain conditions.

Landwer learned to sail as a kid, but for the average adult wanting to get into the sport there is no clear route. You need a boat of your own, or you need an “in.” Landwer and two sailing partners bought a Mac boat of their own a few years ago, a used Farr 40 that set them back $275,000.

That was just the boat. A new main sail costs $18,000 and to remain competitive, that sail should be replaced every year. Docking such a boat in Chicago runs $8,000 a month. Then there’s winter storage, various other equipment costs and hiring a few professional sailors for the Mac Race. Landwer estimates that it costs about $60,000 a year to keep that boat racing.

The only thing that’s free is the wind. Well, a few crew members are free, too. They are the people who volunteer their time and energy to keep the boat moving fast. But a boat is not going to accept just anyone. You need someone to vouch for you.

“On our boat we always like to bring new people in,” says Landwer. This year he will start his 34th Mac Race on a J/111, a 36-foot One-Design. But simply showing up on the docks rarely works.

“The last thing I’m going to do is take someone I don’t know out,” says Landwer. “The wind starts blowing 20 or 25 [knots] and all of a sudden they’re a liability.”

The wind blows that fast and much faster in the Mac. In 2002 it blew 65 to 70 at times, helping Roy Disney (Walt’s nephew) and his yacht Pyewacket set the Race’s most current monohull record: 23 hours, 30 minutes and 34 seconds. The multihull record was set in 1998 by adventurer Steve Fossett on the catamaran Stars & Stripes, which finished in 18 hours, 50 minutes and 32 seconds. Most boats finish in the 40- to 60-hour range, or, when the wind is nowhere to be found, much longer.

So the race is frightening at times, boring at others, and always an expensive pursuit. But anyone who has raced it will never forget how dark the sky is and how bright the stars shine in the middle of our inland sea. Those sailors will forever be a tiny part of one of the grandest traditions our city has ever known.