Strayed was born in Spangler, Pennsylvania, the daughter of Barbara Anne "Bobbi" (née Young; 1945–1991) and Ronald Nyland. At age six, she moved with her family to Chaska, Minnesota. Her parents divorced soon after. At the age of 13, she moved with her mother and stepfather Glenn Lambrecht, along with her two siblings, Karen and Leif, to rural Aitkin County, where they lived in a house that they had built themselves on 40 acres. The house did not have electricity or running water for the first few years. Indoor plumbing was installed after Strayed moved away for college. She later re-connected with her half-sister from a previous relationship of her father.

In 1986, at the age of 17, Strayed graduated from McGregor High School in McGregor, Minnesota, where she was a track and cross country Runner, Cheerleader, and homecoming queen. She loosely based the fictional Coltrap County in her novel Torch on McGregor and Aitkin County. Strayed attended her freshman year of college at the University of St. Thomas in St. Paul, but by her sophomore year, she transferred to the University of Minnesota in Minneapolis, where she received her Bachelor of Arts degree, graduating magna cum laude with a double major in English and Women's Studies. In March 1991, when Strayed was a senior in college, her mother, Bobbi Lambrecht, died suddenly of lung cancer at the age of 45. Strayed has described this loss as her "genesis story". She has written about her mother's death and her grief in each of her books and several of her essays.

Strayed married Marco Littig in August 1988, a month before her 20th birthday. They divorced in 1995, shortly before she started hiking the Pacific Crest Trail.

Strayed subsequently married filmmaker Brian Lindstrom in August 1999. They have two children and live in east Portland, Oregon, where Strayed has lived since the mid-1990s. Her daughter, Bobbi Strayed Lindstrom, played the younger version of Strayed in the film adaptation of Wild.

In addition to her four books Wild, Tiny Beautiful Things, Brave Enough, and Torch, Strayed has published essays in various magazines, including The Washington Post Magazine, The New York Times Magazine, Vogue, Tin House, The Missouri Review, and The Sun Magazine. Her work has been selected three times for inclusion in The Best American Essays ("Heroin/e" in the 2000 edition, and "The Love of My Life" in the 2003 edition, and "My Uniform" in the 2015 edition). Strayed was the guest Editor of The Best American Essays 2013. She won a Pushcart Prize for her essay, "Munro Country," which was originally published in The Missouri Review. The essay is about a letter Strayed received from Alice Munro, when she was a young Writer and Munro's influence on Strayed's writing.

Strayed worked as a waitress, youth advocate, political organizer, temporary office employee, and emergency medical technician throughout her 20s and early 30s, while writing and often traveling around the United States. In 2002, she earned a Master of Fine Arts in fiction writing from Syracuse University, where she was mentored by Writers George Saunders, Arthur Flowers, Mary Gaitskill, and Mary Caponegro.

Strayed's first book, the novel Torch, was published by Houghton Mifflin Harcourt in February 2006 to positive critical reviews. Torch was a finalist for the Great Lakes Book Award and selected by The Oregonian as one of the top ten books of 2006 by Writers living in the Pacific North West. In October 2012, Torch was re-issued by Vintage Books with a new introduction by Strayed.

In June 2012, Wild was chosen as the inaugural selection for Oprah's Book Club 2.0, which is a relaunch of Oprah's Book Club, which ended in 2011. Oprah's Book Club 2.0 uses online social media such as Facebook and Twitter. Winfrey discussed Wild in her video announcement of the new club. Winfrey interviewed Strayed for a two-hour broadcast of her show Super Soul Sunday on her OWN Network.

A long-time feminist Activist, Strayed worked in her twenties as a political organizer for the Abortion Rights Council of Minnesota, which is now called Minnesota NARAL, and also for Women Against Military Madness, a feminist peace and justice nonprofit organization in Minneapolis–Saint Paul. She served on the first board of Directors for Vida: Women in Literary Arts and has been active in many feminist and progressive causes.

The film adaptation of Wild was released on December 3, 2014 in the United States with Actress Reese Witherspoon starring as Strayed. The film was directed by Jean-Marc Vallée and distributed by Fox Searchlight Pictures. Witherspoon optioned Wild for film with Producer Bruna Papandrea for their production company, Pacific Standard, a few months before Wild was published. The book was adapted for the screen by Nick Hornby. In October 2013, the film went into production with Witherspoon in the lead. The cast includes Laura Dern (as Strayed's mother, Bobbi), Strayed's daughter Bobbi Strayed Lindstrom (as the young Cheryl), Gaby Hoffmann, Thomas Sadoski, Michiel Huisman, and Kevin Rankin among others.

Strayed's fourth book, Brave Enough was published in the United States by Knopf on October 27, 2015 and in the United Kingdom a week later by Atlantic Books. It debuted in the advice and self-help category on the New York Times Best Seller list at number 10.