Sailing Magazine : The Beauty of Sail

More than 400 boats and crews will sail from Chicago in the 100th Race to Mackinac—no one can say what they’ll encounter, besides one of life’s great sailing experiences

In the northern reaches of Lake Michigan, nature in its most pristine form is boundless. Towering sand dunes make up the mainland Michigan shore. Islands, many uninhabited by humans, dot the horizon. As you sail farther north, the scent of pine fills the air, and yes, you can drink the cold, crystal clear water.

It is here, in this most unlikely place to find a long-distance sailboat race course, where the Chicago-Mac Race is often won or lost.

The challenge found in the second half of the 333-statute-mile race, where knowledge of local conditions, weather patterns and a great deal of luck determine a competitor’s fate, is what keeps sailors coming back year after year—decade after decade, even—to the longest annual freshwater distance race in the world.

Officially it’s called Chicago Yacht Club’s Race to Mackinac, but to the thousands of sailors who take part in the annual ritual it’s “The Mac,” or, if necessary to delineate it from its sister race up Lake Huron from Port Huron to Mackinac Island, the “Chicago-Mac.” On July 19, a record fleet of up to 460 boats will cross a starting line about a mile off Chicago’s skyscraping skyline for the 100th Race to Mackinac.

This year’s fleet is a far cry from that of the first race in 1898 when five boats sailed an informal race to the resort island at the intersection of lakes Michigan and Huron. The race was held again in 1904 and then it was sailed intermittently until after World War I. It has been sailed continuously since 1921.

The boats that sail the Mac now range from 33-foot Tartan 10s, to sturdy cruisers, to high-tech maxi racers built to break some of the world’s most esteemed sailing records, but many crews will have something in common with the crew of the first Mac winner, the sloop Vanenna, and her 1898 competitors: They’ll be made up family and close friends.

“That’s part of what makes the Mac such an enduring tradition,” said Race Chairman Greg Miarecki, who has sailed all but one of his 22 Mac races with his father, several with his mother and all with close friends, mostly aboard the family’s Ericson 35 Providence. “This is not like the NFL where a player often finds himself playing on a team with people he really doesn’t know. In order to effectively compete, you almost have to sail with a cohesive group of friends or family. That’s the reason the race is so special.”

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Although the occasional professional crew can be found in the race, skippers with amateur crews relish the opportunity to sail against some of the best sailors in the world.

Chris Dickson, head of the United States’ 2007 America’s Cup entry BMW Oracle, sailed on Larry Ellison's Sayonara. Famed billionaire adventurer Steve Fossett sailed Stars & Stripes, the former America’s Cup catamaran in the 1998 race. Other famous sailors who have done the race include Gary Jobson, Ted Turner, Dawn Riley, Bruce Kirby and scores of other luminaries.

But it is Turner who is perhaps most famous for underestimating the race. Having never sailed the Mac before, Turner was warned that Lake Michigan can dish up some particularly challenging conditions at times. Having thousands of ocean miles under his belt, Turner’s reply was akin to a guffaw: “Yeah, I’m really scared.” Later, with his 12-Meter American Eagle and his crew bruised and battered in a fearsome northerly gale, Turner famously proclaimed, “I hereby publicly retract anything and everything I have ever said about inland sailing.”

Eagle was the first to cross the finish line, but took second overall to the Gary Mull-designed 55-footer Dora. Of the 167 boats that started the race, 88 dropped out.

The story of Turner’s retraction is legendary among Mac sailors, and anyone who has sailed enough races can relate to it. Mac races are full of surprises.

The race starts in the company of a vast spectator fleet (the main feature of which is the Coast Guard cutter that accompanies the fleet up the lake—for years the majestic Mackinaw) off Chicago after a parade of boats past Navy Pier and ends 289 nautical miles later off quaint Mackinac Island. But race veterans will tell you that the Mac is really made up of three races: up the open portion of the lake to Point Betsie, past Gray’s Reef and the Manitou Islands, and from the turning mark of Can 3 where the Mackinac Bridge comes into view and the race for the finish line intensifies.

“I could easily start the Mac at Point Betsie,” said Chicagoan Tom Neill, who will sail his 36th Mac race this year on his Great Lakes 70 Nitemare. “The tactical aspect of the race to Point Betsie is not so much tactics as it is which side of the course you play. Then, once you get there, and invariably the fleet comes back together, on every boat I’ve ever been on, you get so reinvigorated. There are boats all over and you start watching them to see if you’re gaining on them. It gets the juices flowing.”

Whether to play the shore, and which one, is the first major decision of the race, although the adage always holds: Get north fast. Once the fleet gets to Point Betsie, the shore again influences tactical decisions. As boats work their way north, the Manitou Passage can often mean feast or famine. Pockets of breeze that can leave boats in millpond-like conditions while their competition slides by in a seemingly private wind a quarter-mile to leeward frustrates and befuddles sailors. Boats are not required to go through the Manitou Passage, and on occasion some bold navigators choose to go outside the islands. It’s a risky proposition. Going outside the islands means sailing extra distance, and parting with almost all your competition. But it can pay off.

Dick Jennings, whose Great Lakes 70 Pied Piper held the race record for 14 years after breaking it in 1987, has gone outside the Manitous twice, and has been successful both times.

“There’s logical reasoning to that decision (to go outside),” Jennings said. “The first time we did it, it worked out very well. We ended up passing larger, faster boats by going outside and ended up finishing first. That was a pretty big kick. It was particularly fun to wake up in the morning and see those guys behind us.”

Fellow Great Lakes 70 owner John Nedeau was not as lucky in his only trip outside the Manitous in last year’s race.

“I was hoping I was as smart as Dick Jennings, but the wind came out of the east as we were coming out and we were cooked,” Nedeau said.

After the Manitous, the fleet goes past Gray’s Reef lighthouse, where years ago spectators would sit on the lighthouse cheering competitors as they passed within yards. These days a noisy flock of cormorants has taken up residence on the lighthouse. Next comes Can 3, where boats make a right turn and head up the Straits of Mackinac. At five miles long, the Mackinac Bridge, the third longest suspension bridge in the world, quickly comes into view, but it’s still 17 miles to the bridge and the finish line is another five miles after that. The Straits can be frustrating. Crews can look forward to a screaming reach, another windless parking lot or something in between. And if they thought the ride to the bridge was long, they’ll be going crazy on the way to the finish line, when the smells of fudge and horses from the island call to sailors but the breeze is often elusive.

More challenging navigation awaits . Graham Shoal, just north of the bridge, beckons sailors with a siren song promising an unfettered breeze away from water-disturbing ferry traffic. But nearly every year, at least one boat ends up on the rocks, just miles from the finish line between Round Island Light and the beach of the Iroquois Hotel, where a crew of volunteers mans the station as the fleet finishes.