Tales From the Great Lakes as Brave Sailors Race From Chicago and Port Huron to Mackinac

Mission Point Resort’s Liz Ware

At the Watery Finish Line with Mission Point Resort’s Liz Ware. Photo by: Emily Daunt, MRLA

The world’s oldest, continuous freshwater sailboat races take place each summer across two Great Lakes over consecutive July weekends: the Chicago-to-Mackinac and Port Huron-to-Mackinac races. It’s hundreds of nautical miles and two or three dramatic days and nights on the water for thousands of sailors on a barrage of boats steered by crew members peering through the mist and humidity for their first sight of the towering “mighty” Mackinac Bridge. But it is the traditional sound of a colonial cannon firing that booms each boat’s finish across the official line at the Round Island Lighthouse at Windemere Point.

Once docked, the Pink Pony Saloon, managed for decades by Brian Bailey and owned by Bob Benser, is the closest immediate relief for the parched, soggy sailors. They deserve a bit of booze before the big bash on the Great Lawn at Mission Point Resort, where the Aperol and awards are poured and presented to the thousands in the formal, shoreline ceremonies a day after each race.

The sailboat racing and events, staged since 1898, may sound as genteel as Mackinac Island’s horse-drawn, Victorian-era luxury lodging. But, usually with a “Dark-n-Stormy” rum drink in hand, the sailors tell tall tales of walls of waves, storm-shredded spinnakers, and, conversely, the dreaded doldrums.

“When it’s really hot with no wind, they sit in the sun and deal with flies out there on the lakes,” said Liz Ware, chair of the Michigan Travel Commission. She and her family own Mission Point Resort. “That’s one of the reasons I have made the trip from Chicago across Lake Michigan to Mackinac Island by powerboat, but not on a sailboat. The races are for people who are really tough, rugged and strong. The conditions they manage range from great wind, no wind, and storms. I have such respect for the really great sportsmen and women who compete in these races.”

Birmingham, Michigan songwriter and singer Robert Dempster was on the crew of Jim Leamon’s 36-foot boat Trim. “Oh yeah, my guitar has got to be with me to play some music and maybe chase away the black flies,” Dempster joked.

“Robert Dempster is the most motivational man that I know,” said Captain Leamon, who needed Dempster, all hands on deck, when Trim and hundreds of other boats had to turn back off Port Sanilac, in Michigan’s Thumb, four hours after their Port Huron start. “An intense storm with 15-foot waves took us and half the fleet for a ride like Disneyland. Water crashing over the bow made the boat more like a submarine.”

Captain Leamon made the decision to turn back when sustained 35-knot winds with overpowering gusts to 45 were knocking their boat dead out of the north – the direction they needed to sail. It was all the crew could do to get the boat to a nearby harbor safely.

“I was in a ‘sea shock.’ When I got to the dock in Port Sanilac, I kissed the ground,” said Dempster. “It was a Great Lakes adventure for sure.”

It wasn’t a storm at the start of the Chicago version of the race, but a collision with another boat that nearly sank the 50-foot yacht MC2, according to Shari Lewis. Her husband was at the helm when the crew discovered the crash broke a two-by-four-foot hole in the port side of the hull.

“They kept racing and bailing water every 20 minutes for hours while trying to patch the hole. They figured they took 200 gallons of water off the boat until they came up with a solution that worked: they pulled apart a Yeti cooler and used a bunch of other materials,” said Lewis.

Amazingly, MC2 reached Mackinac Island fast enough to still finish in third place! The crew then sailed her to Port Huron, where the boat underwent fiberglass and epoxy repairs just in time for Saturday morning’s start of the Port Huron-to-Mackinac race. MC2’s crew, with little sleep, then managed to sail through the aforementioned fierce storm on Lake Huron that ended the race for more than 80 boats.

“They hung on and never had an issue with the repair work,” said Lewis. “The grit, determination and tenacity of this crew is just unmatched. They’re like extended family to us.”

The Ware families’ waterfront Mission Point Resort is the award-bash venue for both races when thousands of sailors gather on the resort’s Great Lawn, and a great view of the lake they just conquered, from an Adirondack chair. The rest of the season, Mission Point is where the Midwest puts its feet up.

Contact Michael Patrick Shiels at [email protected]  His new book: Travel Tattler – Not So Torrid Tales, may be purchased via Amazon.com Hear his radio talk show on 730 AM 1240 in Lansing weekdays from 3 pm – 6 pm. 

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