Mackinac Solo Sailors Brave Rain, Smoke, Bats in 45th Race to Island

This story first appeared in the July 7, 2023, Mackinac Island Town Crier print edition

About 40 sailboats of all lengths and mast heights lined up at either side of Michigan’s mitten Saturday, June 24, with half of the boats on Lake Michigan sailing out of Chicago, and the other half on Lake Huron sailing out of Port Huron. It was the start of the Great Lakes Singlehanded Society’s Mac Solo Challenges, a series of six sailboat race challenges either finishing at or at least passing Mackinac Island.

Jeff Stack, a skipper departing from Chicago aboard Gabriel for the Chicago to Mackinac Island Challenge, said the boats were all lined up going the same direction only at different speeds.

“It’s kind of like the start of the running of the bulls,” Mr. Stack said.

Despite their differences, the boats all had one thing in common: only one sailor – the skipper – was aboard. They are called solo challenges, Mac Solo Challenges Chair Elisabeth Reichling said, because being out on the water sailing a boat alone is difficult, and finishing is a challenge. And the race has a competitive atmosphere.

Mike Tobey accepts his President’s Challenge Cup. Mr. Tobey finished second in the Ontario division of the Chicago to Mackinac Island Challenge on his boat Syzygy. He won the award for competing and finishing his first solo challenge with the Great Lakes Singlehanded Society. 

“Put two sailboats on the water within sight of each other, and they’re racing,” she said. “Whether they admit it or not.”

Days later at the Mackinac Island Yacht Club Wednesday, June 28, the dining room was full of laughter, chatter, and stories from “back in my day” for the awards luncheon. It was the 45th Port Huron to Mackinac Island Challenge, the 27th Chicago to Mackinac Island Challenge, the eighth triennial Super Mac Challenge, and the sixth triennial Super Mac and Back Challenge. The race committee was stationed at the yacht club since Sunday, June 25, preparing for their arrival. The club hosts the challenges every year on behalf of host Richard Lappin, who has been a member of the yacht club for 23 years. Mr. Lappin attended the luncheon, having completed 33 solo challenges in his lifetime. Some skippers have finished 40 or more solo challenges.

“People say we’re crazy,” Ms. Reichling said at the award ceremony. “And I say, ‘Nope, we’ve all been tested. We’re just a little weird around the edges.’”

Mr. Lappin’s boat Ginger Key started the challenge in Port Huron but didn’t finish this year. No matter the results, the skippers reveled in the camaraderie and passed around a flag to sign that will be gifted to another skipper who couldn’t make the challenges this year.

“They all feel like family,” Ms. Reichling said. “You may only see them twice a year, but family is family.”

“This group is unique,” Mr. Lappin agreed. “It’s a unique set of characters.”

The awards luncheon recognized everyone who finished the solo sailing challenges with special flags. Participation pennants and larger flags for first, second, and third place racers for each division were also handed out. The two skippers who finished their first Great Lakes Singlehanded Society challenges (the only requirement to join the society) received special flags, as did the Pickle Award winner, given to the skipper with the longest finishing time. There were four divisions in the Chicago race and three in the Port Huron race, which were determined by performance handicap racing fleet handicaps. At least seven sailors were unable to finish, and at least four didn’t start. The flags were new this year, meant as placeholders for cast medallions that the sailors will receive in a few months. In previous years, the skippers received disks until their medallions arrived.

As each skipper walked up to receive their award, they were invited to share a favorite memory or story from this year’s race. The skippers regaled their peers with tales of harsh weather, bantering on marine VHF radio channel 72, sleepless nights, and even at least one encounter with bats.

After corrected speeds, the winners of the Chicago challenge were Ralph Krauss aboard Yukon in the Michigan division, Mark Mahowald and Strider in the Ontario division, Todd Gayley and Touring Machine in the Erie division, and John Hoskins and Madcap Spot in the Superior division. Madcap was also the first boat to cross the finish line. In the Port Huron challenge, Robert Schroer and Tweety won the Michigan division, Karim Botros and Havannah won the Ontario division, and Joey Baker and Harmony won the Superior division.

Mr. Botros started sailing as a little kid in New York and, three years ago, heard about the Great Lakes Singlehanded Society community. He completed the Lake Erie Solo Challenge two years ago, but this year was his first time sailing to Mackinac Island in the solo challenges. Before that, he had done around 17 other races to Mackinac. He recalled the banter on the radio fondly, everything from the skippers helping each other solve problems and sharing weather updates to “There’s a bat in my boat!”

“It’s a different camaraderie that you don’t normally see in a race,” he said. “You know that you’re not alone out there.”

Skippers in one of four other concurrent challenges, the Super Mac and Super Mac and Back challenges, passed the Island finish line for the regular race and continued to one of the starting ports. One of the hardest parts about the longer challenges, many of the skippers agreed, is passing the Island to continue racing, because those who do miss out on the awards luncheon and will be on the water for days, maybe weeks, afterward.

Two sailors also won the President’s Challenge Cup, an award only for firsttime finishers on any one of the lakes. It isn’t awarded every year, and sailors only have one chance to win it by competing and finishing their first challenge. One sailor from each lake took home a President’s Challenge Cup this year: Mike Tobey on Syzygy for Lake Michigan and Ben Thorsen on Scarlet Fire for Lake Huron .

Mr. Tobey of Whitefish, Montana, now lives in Chicago and owns a manufacturing company. His finishing status gave him lifetime membership in the society, and he said he looks forward to returning. Being the owner allows him the flexibility to participate in events like this.

“It was such an incredible experience,” Mr. Tobey said. “Definitely one of the top things I’ve done in my life.”

He started sailing 12 years ago and had done a few Mackinac Island crew races before, but this was the first one on his own. He recalled the wonderful moments on the water, taking everything in, sailing in the middle of the night in complete darkness, not a single light on the horizon. He said he’d always been attracted to the idea of just him and the boat. As a self-admitted rookie in the group, he gave the challenge veterans a run for their money – at the very least with how to pronounce the name of his boat. It’s Syzygy, pronounced ‘sizz-ehgee,’ meaning the alignment of celestial bodies.

Tailing Mr. Tobey through the finish line was Mr. Stack aboard Gabriel, a skipper who has raced in the Mac Solo Challenges for 11 consecutive years. He loves his boat, and his good luck charm on the water is a six-pack of beer. After a brutal rainstorm with unbelievable wind, soaked to the bone the whole time, he thought about pulling out of the challenge, until he called his wife.

“She said, ‘No! You’re picking me up in Petoskey, you have to finish!’ So, I said ‘Okay,’” Mr. Stack said, “and I pressed on.”

Mr. Stack, too, lives in the Chicago area, and enjoys being alone on the water away from the hustle and bustle of people he finds “aggravating.” And if the brutal rain at the beginning of the race was a punishment, the finish line was the reward.

“It was glorious,” he said. “It’s like a vacation to me. A physically exhausting vacation that I look forward to, to be around my friends.”

Mr. Stack was a shepherd this year, something he considers a great responsibility and honor. The shepherd and flock system is one of the ways the skippers and race committee keep track of where the boats are, making sure everyone is okay. Ms. Reichling tried to introduce more ‘nautical’ terms to the group during the luncheon, instead of the shepherd and the flock, and was swiftly met with outcries. They also do radio check-ins every six hours, with other safeguards in place to keep track of the boats, such as trackers.

“We worry about each other, and we are our own backup,” Ms. Reichling said, “until you call the Coast Guard.” And they did have to call the Coast Guard this year. The skipper and his boat were fine, but his communications had failed.

When the skippers do finally cross the finish line at the Island, which is between a green buoy beyond the harbor and a piece of blue painters’ tape on the window of the Mackinac Island Yacht Club’s dining room, they all get the same welcome: “Congratulations, you have finished the Mac Solo Challenge. Welcome to Mackinac Island.” But that doesn’t mean the challenge is completely over. After a boat comes in, the race committee boards it for an inspection, checking things like fire extinguishers. Skippers must take the inspection paperwork, signed appropriately, into the yacht club along with radio logs for another round of paperwork signing.

“And then, they get a bottle of rum,” Ms. Reichling said, and they are officially done.

They used to give out the rum before the paperwork was turned in. That was a mistake.

It takes a lot to complete a single-handed sailboat race. And yet, the skippers of the Great Lakes Singlehanded Society offer lots of reasons, explanations, and justifications for coming back, year after year, for a few days of solitude and sometimes bad weather in the Great Lakes. There’s camaraderie and friendship. There’s a family and tight knit community. There’s strength and accomplishment. There’s endless banter, tips, and words of encouragement on radio channel 72. They’re also a little bit weird.

“The people who do these long courses are a little weirder than the rest of us,” Ms. Reichling said.