Matriarchs of Grand Marais: Portraits honor women who shaped our community

Chuck Olsen | September 10, 2025

On a late summer afternoon, Anna Hamilton stepped into a modest artist studio tucked inside Jan Attridge’s home. Displayed on an easel was a portrait of Anna and her sister Sarah — the latest addition to The Matriarchs of Grand Marais, a portrait series celebrating women whose work has helped shape the Grand Marais community.

“The painting is incredible, and the honor is incredible,” said Hamilton, who co-founded the non-profit Hamilton Habitat with her sister. “It’s called The Matriarchs, and I’m not really certain what that means.”

Attridge, who has lived and painted in Grand Marais since 2005, explains the title. “I thought, this is a town of matriarchs,” she said. “Women who had dreams, involved their families, kept them growing, and connected with the whole community.”

Jan Attridge and Anna Hamilton with portrait

A portrait series rooted in community

Attridge has painted 9 portraits for the series, which now includes names and faces familiar to Cook County residents: Ann Jorgenson of Java Moose, artist Betsy Bowen, Sue Hennessy of the Grand Marais Playhouse, Deb Benedict of WTIP, Sherrie Lindskog of World’s Best Donuts, Lois Eyink, Jan Smith, Anna and Sarah Hamilton, and Joan Farnam.

The series began when Attridge painted Jorgenson as a birthday gift, a project that grew into an ongoing series to honor local women.

Anna Hamilton’s mark on Cook County

Hamilton and her sister Sarah have left their imprint on Cook County in more ways than one. For decades, they ran restaurants that became gathering places for locals and tourists alike, including Trail Center, My Sister’s Place and Huey’s Taco House.

More recently, the Hamilton sisters turned their energy to one of the county’s toughest challenges: affordable housing. In 2018, they launched Hamilton Habitat, a nonprofit that builds homes at cost and sells them directly to residents in Cook County.

“We just thought, what the heck could be so hard about building a house? So we did it,” Hamilton said. “We don’t make money on these projects. We want people to own their homes. Equity is sometimes the only thing the working stiff ever gets out of all their labor.”

So far, Hamilton Habitat has completed nine homes, with two more under construction this winter.

“It’s not that we’re doing great things,” Hamilton said. “It’s that we’re doing something.”

A lifetime of painting people

For Attridge, the Matriarchs project is the latest chapter in a lifetime of painting the people around her. Raised in rural Marshall, Minn., she began with portraits of neighbors and small-town life.

Her career later took her to Minneapolis, where she worked at the Guthrie Theater and Minnesota Opera, dyeing costumes and painting large scenic backdrops. Those years, she said, gave her the technical discipline she still relies on in her portrait work.

In the 1970s, Attridge turned her attention to activism, painting leaders of the American Indian Movement such as Clyde Bellecourt and John Trudell. She immersed herself in survival gatherings and protests, documenting a moment of change for Native communities.

Now, in Grand Marais, her focus is on the women who make the town run. As she flips through her book of portraits, each face prompts a story: a family business passed down, a theater kept alive, a nonprofit built from scratch.

Honoring the everyday leaders

For Attridge, the definition of a matriarch is simple.

“It’s watching a woman have a dream, then figure out how to do it, working through the problems until it becomes real,” she said.

Hamilton, still staring at her own portrait, admits the word feels heavy. But she agrees that the women who choose to stay in Cook County often do so out of a sense of purpose. “The people that choose to live here need it,” she said. “They need the woods, the water. This place saved me. And that’s part of why we do what we do.”

Attridge nodded. “That’s exactly why I’m doing this. Thank you, God.”

With each brushstroke, she continues to honor the women who keep Grand Marais rooted and resilient.