Cheryl Strayed was born on September 17, 1968 in Spangler, Pennsylvania. She is the daughter of Barbara Ann "Bobbi" Young Nyland and Ronald Nyland; Cheryl changed her surname to Strayed as an adult. Cheryl's parents divorced when she was six, shortly after the family (which included her two siblings, Karen and Leif) relocated to Minnesota. Cheryl grew up raised by her mother and eventually her stepfather, Glenn Lambrecht. When she was thirteen, the family moved to a plot of land in a rural area of Minnesota where they built their own house over a period of several years, often living without electricity or running water.
Strayed attended high school in Minnesota where she competed as an athlete and was also crowned homecoming queen. After graduating in 1986, she started college at the University of St. Thomas before transferring to the University of Minnesota to complete her degree. During her time as a student, Strayed married Marco Littig. In 1991, as Strayed was completing her final year of college, her mother died of cancer at age 45, only a few months after receiving a diagnosis.
After her mother's death, Strayed worked in a number of fields, including as a waitress, youth worker, and political organizer. She also began developing her portfolio as a writer, publishing essays and short fiction. She divorced from her first husband in 1995, and a few months later she hiked the Pacific Coast Trail. Shortly after completing the hike, she relocated to Portland, Oregon where she has lived ever since. She remarried, to filmmaker Brian Lindstrom, in 1999. In 2002, Strayed completed her MFA from Syracuse University. Her first novel, Torch, was published in 2006. In 2009, she was awarded the Pushcart Prize for her essay, "Munro Country" which was published in The Missouri Review. Beginning in 2010, Strayed took the over popular advice column "Dear Sugar" which was published on the website The Rumpus. She wrote the column anonymously for 2 years before revealing her identity.
In 2012, Strayed published both Wild, a memoir about her experience hiking the Pacific Coast Trail, and Tiny Beautiful Things, a collection of the columns she had published as Sugar. Wild's huge success has made her an influential speaker and writing coach. She was also involved in the film adaptation. Between 2014 and 2018, Strayed co-hosted an advice podcast called Dear Sugars with Steve Almond.
Strayed has lived in Portland, Oregon since 1995. She and her husband have two children, a son named Carver, and a daughter whom she named Bobbi, after her mother.