The Big 5.0.: Wilmette-raised Gail McCarthy has sailed Chicago to Mackinac more times than any other woman

The Mackinac race is one of the most well-known freshwater races in the United States, and just 428 sailors have reached Island Goat status, completing at least 25 races. Only 33 women appear on that list.

But an even more exclusive milestone exists: 50 races — a mark that, until this July, had been reached only by men.

Then Gail McCarthy set sail for this year’s Mackinac race on July 11.

Roots

McCarthy was raised from the fifth grade onward in Wilmette. She attended now-defunct Howard Junior High, then New Trier East High School before going to college at the University of Wisconsin-Madison.

Her sailing journey began when she was a child, and her father, Gene McCarthy, was a decorated competitive sailor himself.

Gene McCarthy became the skipper with the most Mackinac races, with 67 completed at the age of 94 in 2024.

But Gail McCathy’s sailing legacy nearly never left the dock. Despite a foundation developed sailing with her father, she faced obstacles along the way.

“My dad came home [one] night and said, ‘I gotta talk to you,’” McCarthy said. “He said one of the partners has decided there will be no women on the boat, and you’re not going.”

This was in 1974, which ironically was a pivotal year for women as they were finally allowed to open credit cards and secure mortgages without a male co-signer.

Starting two years prior, in 1972, the Equal Employment Opportunity Act allowed women equality in the job market and Title IX prohibited sex-based discrimination in education, dramatically expanding women’s opportunities in school athletics.

Despite Title IX, women still found trouble gaining equality on the water.

So 1974 was one of few Mackinac races Gail McCarthy did not sail. But the very next year, when she turned 18, she sailed the Mac on a separate crew.

Since her first crossing in 1975, the only other race McCarthy has missed was in 2020, when the race was canceled because of the COVID-19 pandemic.

Journey

When McCarthy talks about her most memorable Macs, she goes back to two: the first one she finally sailed in 1975, a four‑and‑a‑half‑day slog of a trip of a race that usually takes 48 hours and that timed out 90 miles short of the island; and the one through a storm in 2011, when 100-mph winds laid her Great Lakes 70 over so far that “the spreader tip (one of the mast’s horizontal support arms) was in the water” and she experienced just how quickly an offshore race could turn dangerous.

After 50 races, McCarthy said this one will likely be her last.

She lives in Michigan and feels that she’s missed a few local sailing opportunities by traveling to Chicago to prepare for this big race.

“I’m probably gonna be done,” McCarthy said. “There are all kinds of things I miss. … These two weekends that, you know, every community has their standard [traditions and races] and it’d be kind of fun to go to some of the stuff I’ve been missing.”

Her 50th Chicago-to-Mackinac Race ended with a win, as she and the Mise En Place crew — with co-skippers Paul Thompson and Karen Harris — finished as the fastest mixed plus boat in the Cruising Division.

The McCarthy legacy is not through, however. Gail McCarthy raised her two children, a boy and a girl, to race and nurtured their passion for the water.

Her daughter, Laura Beck, also sailed on the Mise En Place to celebrate her mother’s accomplishment, and thanked her mother for her zeal for the sport.

“I think my mother has influenced me in sailing by, one, being very young and then not giving me a choice,” Beck said.

Today, Beck works as a certified marine engine tech and has a job at the Chicago Harbors, where she’s one of few women on the job.

As a child, Beck also noticed the shortage of women on the water.

“When I was really, really young, there was a very noticeable lack of women and even children in keelboat racing around just Chicago in general,” Beck said.

Through McCarthy bringing her daughter to her races and teaching her how to work a boat, she was able to add one more woman to the exclusive boys club that is sailing.

The 2026 Mackinac race marked Beck’s return to the spot, but she’s following in her mom’s footsteps. It was her 23rd Mac race.

Although it’s not the first time they accomplished this journey together, Beck was emotional knowing it would be their last. She said her eyes well with tears whenever she reminisces of sailing with her mother.

“I’m really proud of her,” Beck said. “I’m fortunate. I’m grateful, and I’m gonna miss seeing her around on the island.”

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