On Saturday, the lakefront will thrill once again to the start of another Chicago-to-Mackinac Island sailboat race. Its sponsor, the Chicago Yacht Club, says the race will be even more thrilling than usual because this is the 100th anniversary of the contest, which began an entire century ago in 1898, in fact.
Many of you will stop, look at the forest of sails on the lake and then wander on. Others of you will stop, look at the forest of sails and wonder, “Who are they? Where are they going? Why are they doing this?” And then wander on.
For those of you in the latter category, and even those of you who might be spending the day in the giraffe house at Brookfield Zoo instead, we offer the following:
Q – Who are they?
A – Unlike loftier competitions, such as the prestigious America’s Cup race or England’s Cowles Race (which appears to be limited to the descendants of Admiral Nelson and listees in Burke’s Twittage), the egalitarian Mackinac contest is open to almost anyone.
The requirements are only that one has a sailboat 27 feet or longer, has rounded up a crew somewhere and belongs to a yacht club. According to Mackinac race chairman George Wolf, this last requirement is to “show they support the sport.” Supporting the sport by jumping up and down on the shore going “Huzzah, huzzah!” or “Go, schooners!” doesn’t count.
Also, the race is limited to the first 300 entries, because that’s all the harbor on the other end will hold and when more try to cram in there are altercations. The Chicago Yacht Club as yet has no trophy for winning altercations.
Q – Where are they going?
A – They are sailing 331 miles (not to be confused with nautical miles, which are like regular miles, only longer and wetter) from the Chicago lakefront to the other end of Lake Michigan and an overrated tourist destination called Mackinac Island, which prides itself in banning motor vehicles and allowing only approximately 100 million bicycles and a few horse-drawn carriages, which can be disagreeable, depending where you step and how fast the bicycle is going when it hits you.
Q–How long does it take?
A–The fastest time (26 hours 50 minutes) and the slowest (62 hours) were both set by the same boat, the Pied Piper, though not in the same race.
Q–Why are they doing this?
A–Some enter the Mackinac because they are keen, highly competitive sailing enthusiasts with seasoned yachting skills and a thirst for adventure. Others do it because they want to show off their big, expensive sailing yachts. Others do it because they discover it’s pretty boring just sitting out there on the lake bobbing up and down. Others do it because you can recruit crews right off the docks and it’s a neat way to meet girls. Still others do it–as they remind themselves when the winds start blowing 50 or 60 knots — because they’re out of their minds.
Q–How did the Mackinac race get its start?
A–According to 100th anniversary chairman Don Glasell, it began with a bunch of guys rich enough to own big sailing boats and summer homes in northern Michigan sitting around bragging about how fast they could sail their boats up there. Someone put his money where his mouth was and the race was on. The winner of that first 1898 contest, with just five boats, was the immortal W.R. Crawford, who never won another one. In fact, the event proved to be so uninteresting they didn’t hold another one until 1904.
Q–What is the most exciting part of the race?
A–Generally speaking, the dockside parties they have the night before in Monroe Harbor. At highest din, they’re remindful of the storied 19th Century Barbary Coast pirates of Tripoli celebrating a particularly good pillage.
Q–Seriously, isn’t the Mackinac race dangerous?
A–Of course. Especially when you get to the island, where they have all those bicycles. Ha ha. Actually, the lake can turn violently tempestuous.
“The thing about Lake Michigan is that it’s long and narrow,” said Glasell, who has obviously been looking at his charts. “You can guarantee you’re getting into a different weather system because you’re traversing so much of the globe. In ’70, there was a big high, a nor’easter. It stayed in the same position for 36 hours and blew 35 miles an hour and more, steady. We had to sail on a beat, and with the wind coming out of the north it built up enormous waves. I remember a wave that was above the spreader.”
A dozen or more boats lost their masts that year, and 88 out of 172 had to drop out of the race. But the Mac’s really not as hazardous as some of the big blue-water contests on the open ocean (after all, you can always make a run for Sheboygan). In the 1979 Fastnet Rock Race in the Irish Sea, 219 of 306 boats sank or had to abandon the competition and 19 sailors drowned.
The only real wreck in a Mackinac race happened during a big blow in the 1911 contest, when a yacht named the Vencedor ran aground on rocks at Fisherman’s Reef and was pounded and mauled by the storm, inspiring a truly dreadful poem called “The Wreck of the Vencedor,” by the immortal Maurice Beam.
In another race, a skipper sailed under the wrong part of the Mackinac Bridge span and knocked off three feet of his mast.
Q–How dreadful is the Vencedor poem?
A–Here’s just a tiny passage:
And ghastly figures, beck’ning, rose from up stark Fisher’s Reef,
Voluptuous forms with virgin’s eyes, that hid ghouls’ vampire teeth.
Thus did dread death-march then begin for graceful Vencedor.
By orchestra of wind and wave — the Sea Gods’ troubadors.
Q–What’s a spreader?
A–It separates the shrouds and stays from one another, lest they get tangled in the halyards, if not the outhaul.
Q–Turn-of-the-century financier and snob J. Pierpont Morgan once said, “You can do business with anyone, but you sail only with gentlemen.” Is the Mackinac like that?
A–Of course not. This is the Midwest.
“Coming out of the East,” said Chicago Yacht Club Commodore Kurt Stocker, “I’d say the uniqueness of this race and this part of the country is it really welcomes a lot of different kinds of people. It may be one of the last big races where you don’t have to come with a professional crew and a huge undertaking and a boat you’re going to use three times before it gets old. And you can compete at the top level. It’s set up so the least of the sailors can compete with the best, and I think this is what brings people in here. I think that’s the Midwestern flavor.”
Q–Have there been any notable international competitors to come out of the Mackinac race?
A–Heck, yes. Buddy Melges of Wisconsin, whom chairman Wolf calls “a beer and a brat guy,” went on to sail in America’s Cup races as well as to skipper the restored giant J-Boat “Shamrock” in a famous exhibition race. Melges has also been known to sail with a manure fork affixed to his mast–possibly to deal with those horse-drawn carriages on Mackinac Island.
Millionaire sportsman Ted Turner sailed in that tempestuous 1970 Mac, and went on to win the America’s Cup in 1977, when he showed up at the victory press conference with a bottle of whiskey. He also survived that deadly 1979 Fastnet Rock Race, lashing himself to his mast and hurling profane oaths at the wind. During the 1970 Mac, he is alleged to have said, “I hereby publicly retract anything and everything I have ever said about inland sailing,” but one suspects his actual remarks were a little pithier.
Another world-class yachtsman–or, if you will, yacht person–out of the Mac is Michigan’s Katie Pettibone. She went on to compete in the America’s Cup lists, and was one of the intrepid surviving crewmembers in this year’s incredibly rugged Whitbred around-the-world sailing race.
Crooked Republican William Hale Thompson won the 1908, 1909 and 1910 Macs (could they have been rigged?) and went on to be the last Republican mayor of Chicago, though not the last crooked one.
Q — Do the boats that finish the Mac first win?
A — You’re confusing this with something sensible, like steeplechase racing. In an effort to give everyone an equal chance at winning (and losing), the Mackinac operates with a choice of two systems of handicapping in which boats have time deducted or added to their actual race time, depending on their size and racing record.
One is a complicated, incomprehensible system called the International Measurement System, which divides the field into three categories of entrants called Section One, Section Two and, yes, Section Three. The other is a complicated, incomprehensible system called the Lake Michigan Performance Handicap Racing Federation rules, referred to as “Perf,” in which boats are divided into Sections Alpha, Beta, Charlie and so on.
Because of these handicaps, Turner was declared the second-place finisher in 1970 even though he crossed the finish line first. And you can bet your booties he was miffed.
Q–What is the best-kept secret of the Mackinac Race?
A–Competitors give false positions over the radio in hopes of luring competitors off course.
Q–What is the worst-kept secret of the race?
A–How the exclusive “Island Goats” club of 25-race Mac veterans got its name. “After two or three days out there,” said Glasell, “they smell like goats.”




