Cheryl Strayed calls upon her Minnesota roots before resurrecting Oprah's book club

The author about 900 miles and two months into her hike, at Crater Lake, Oregon in August 1995
courtesy of Cheryl Strayed

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Slideshow: Cheryl Strayed in the wild

Cheryl Strayed has made transformation stories something of a career.

Her memoir, Wild: From Lost to Found on the Pacific Crest Trail, hit shelves March 20. A few weeks later, she got a call from a number she didn't recognize. Oprah Winfrey was on the line.

The mogul had just finished Wild. She loved it enough, she told Strayed, that she wanted it to launch a new version of her famous reading group, "Oprah's Book Club 2.0." Not long after, Strayed was hanging out in the backyard at Oprah's Santa Barbara estate.

Now, Wild has sold 500,000 copies (including print and digital) and been on the New York Times bestseller list for 20 weeks. NPR praised the book as "One of the most original, heartbreaking, and beautiful memoirs in years;" the New York Times Book Review described it as "spectacular" and "a literary and human triumph." Reese Witherspoon's production company quickly snapped up the movie rights.

"It's been like a bomb going off. Just beyond my wildest expectations," Cheryl Strayed says from her hotel room in Raleigh, North Carolina, the latest stop on her months-long book tour.

It's about as far as she could have gotten from her hometown of McGregor, Minnesota. Strayed always knew she wanted to get out of McGregor, but the drive to flee Minnesota entirely came later, after her life disintegrated here. In her final semester at the U of M, her mother died suddenly and Strayed entered a downward spiral. At bottom, she was a divorced college dropout flirting with a heroin problem.

To pull herself back out, Strayed decided to hike 1,100 miles on the Pacific Crest Trail, from California's Mojave Desert up to the Oregon-Washington border. Wild tells the story of her three months in the woods with nothing but herself, a comically oversized backpack nicknamed "Monster," and her hiking boots (or, for a few hairy days after she lost a boot over the edge of a cliff, her duct-taped camp shoes).

When Strayed left for the PCT, she also left Minnesota. Being in the state where her life fell apart hurt too much. She lives in Portland now, but she'll be in town for three appearances in October. And Minnesota is still, she says, the place that feels like home.

"Minnesota is my people, my place," Strayed tells City Pages. "But it's one of the most complicated emotions I think I've ever had about anything, the way I feel about Minnesota."

Strayed moved to Aitkin County from Chaska when she was 13, growing up on 40 acres of woods and farm in a house her mother and stepfather built by hand.

The area was rural. Even today, the entire county has just one stoplight, and the 2010 census tallied only 391 residents of McGregor. But McGregor was just the closest town. Strayed lived even farther out in the middle of nowhere — 20 miles south of town in Beaver Township. She was the last stop on the school bus and had a three-hour daily commute.

"There weren't a lot of people up there that didn't have running water and didn't have electricity," says Strayed's high school English teacher, Ginny Wallace. "But she didn't have either one."

Not only was Strayed the new kid in a small town, but her family lived back-to-the-land style, which didn't exactly help her fit in with her classmates.

"We were seen as hippies," Strayed says. "My mom made clothes, and gardened, and she did stuff like didn't shave, which I was just horrified by."

Desperate for acceptance, Strayed invented a persona as a cheerleader and a homecoming queen.

"Cheerleaders are more beloved than the smart girl sitting at the back of the room reading Jane Eyre," Strayed says. "The real me was the girl reading, but I pretended to be that other person to survive."

Strayed was always ambitious — "since I was like four," she says — and did well enough in school to get into the University of St. Thomas. By the time she moved to the Twin Cities for her freshman year of college, she was ready to shake off the north woods.

"In some ways I over-corrected from that small-town self," Strayed says.

She bought groceries at the Wedge and at Mississippi Market, and hung out at the 400 Club, the New Riverside Cafe, and the Uptown Bar. ("Is the Uptown Bar still around?" she asks, smiling. When she hears that it shuttered in 2009, she responds, "Oh. Yeah, when I drove through Uptown the last time I was in town it's just like, well what happened to Uptown?").


She transferred to the U for her second year of school and started taking writing classes. Her senior-year fiction professor, Paulette Bates Alden, remembers her as driven.

"Cheryl from the beginning had a particularly keen interest in writing," Alden says. "There was this material that was different than your usual background — this rural, almost hand-to-mouth existence up there in the northern woods — and also this tremendous ability to describe it and capture it."

Tragedy struck during Strayed's senior year, when her 45-year-old mother was diagnosed with lung cancer. Just seven weeks later, she was dead. A grieving, shattered Strayed failed to finish her last semester of school and started cheating on her new husband. She found work as a political organizer with Women Against Military Madness and what's now known as NARAL Pro-Choice Minnesota. After realizing she didn't have time to both organize and write, she quit to waitress her way through the bills, and worked at Nikki's Cafe in the Warehouse District and at Mitterhauser's on Lyndale.

In the following years, the first half of the '90s, she rambled around the country, endured a painful divorce, fell in love with a heroin junkie, and started experimenting with the drug herself.

Strayed knew she needed to transform. First, in a conscious stab at reinvention, she dropped her given surname, Nyland. Her family had drifted apart in the wake of her mother's death, and she wanted to christen herself with something that seemed more her own. She was a stray, she felt, and she had strayed.

The writer Barrie Jean Borich met her around the time of her name change and remembers Strayed traveled light.

"Her only possession was her truck," Borich says. "I think she was even living in her truck at one point."

Struggling, Strayed thought of a book she had seen in the checkout line at the REI store in Bloomington. It was a guide to the Pacific Crest Trail. The grueling challenge, the 26-year-old decided, would give her the tools, and the clean slate, to remake herself. More than 15 years later, her months on the trail would also provide the narrative arc for her book.

"The thing about Wild is that it does follow a popular structure," says Borich, who teaches creative writing at DePaul University in Chicago. "That's the reason it gets on Oprah's list. It's a very readable book in that way. But she doesn't just rest on that structure, she challenges it. She doesn't go for easy redemption, and the writing is so strong that she manages to do both convention and art."

Part of the strength of that writing is its intimacy. Which means that sometimes, when she's standing in front of a packed room of strangers on tour, "it can be kind of squirmy," Strayed says.

"I'm up there in front of an audience and I'm telling people about my mother dying, or about being promiscuous, or about funny things too, like my husband spanking me when we first met. I sort of go, 'Gulp, here we go!'"

In July, Strayed published her second book of the year, Tiny Beautiful Things, a collection of her "Dear Sugar" advice columns for the literary website the Rumpus. Like Wild, the work aims to use Strayed's journeys to help her readers find their own way to transform.

This ability to make her audience's problems her own — to relate — is one of the key components of Strayed's success. Borich was walking with her at a writers' conference in Chicago when she experienced this first-hand.

"There were these women coming up to her and throwing themselves at her feet, saying, 'You saved my marriage,'" Borich recalls. "There's something about her that invites that."

Strayed is still, however, a Minnesota girl at heart. She doesn't just say thank you to these fans and walk away, says Borich. "She talks to them."

Strayed lives in Portland now, with her husband and their two kids, not far from where she ended her hike on the PCT in 1995. Coming back to Minnesota can be painful for her.

"It's like I have a ghost life in Minnesota," she says. "If I wanted to go spend Thanksgiving in Minnesota with 'my family,' I couldn't. I'd have to get a hotel room and say, 'I'll cook turkey there.' I feel those things when I go to Minnesota."

She comes to the Twin Cities on book tours, and will be in town for three nights in October doing readings. But the last time she was in Aitkin County was in 2009, to write a part of Wild that she describes as "the hardest thing I've ever written." It's a scene that recounts how she, her then-husband, and her brother had to kill her dead mother's horse. Strayed couldn't afford a veterinarian, and the three had to shoot the sick animal themselves.


She had a reading at Hamline University, and decided to extend the trip in order to write the painful passage. Strayed found a retreat about 10 miles down the road from her old home. When she got there, she realized her stepfather, a carpenter, had built the cabin.

"He has a very recognizable style. It looked like my house," she says, before correcting herself. "I mean the house where I grew up."

Strayed spent the next five days writing the horse scene "over and over, and over and over, and over," she says. "It was intense. But it was the right place to be doing it."

Though she doesn't return often, she's been happily surprised by the reception she's gotten in McGregor. People back in her hometown have read her books — the East Central Regional Library System has six copies each of Wild and of Strayed's previous book, Torch, an autobiographical novel set in a McGregor stand-in. Old friends have reached out with congratulations.

"So many of those people I thought would cast me out actually welcome me into the fold, and they're really proud," Strayed says. "I'm not speaking for the whole town. But a few dozen people from that time in my life have been incredibly supportive."

The acceptance is meaningful, Strayed says, and Minnesota continues to be an important part of her work. For the author now, even though Oregon is home, "Minnesota is home home," she says.

"I look out across the landscape, and I just think, in some ways this is where I belong and always will." 

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