Strayed was born in Spangler, Pennsylvania, the second daughter of Barbara Anne "Bobbi" (née Young; 1945–1991) and Ronald Nyland.

When Cheryl was 12 her mother married Glenn Lambrecht, and the following year the family moved to rural Aitkin County, where they lived in a house that they built themselves on 40 acres.

In March 1991, when Strayed was a senior in college, her mother, Bobbi Lambrecht, died suddenly of lung cancer at the age of 45.

[6] Strayed has worked as a waitress, youth advocate, political organizer, temporary office employee, and emergency medical technician[7] throughout her 20s and early 30s, while writing and often traveling around the United States.

[11] She wrote the column anonymously until February 14, 2012, when she revealed her identity as "Sugar" at a "Coming Out Party" hosted by the Rumpus at the Verdi Club in San Francisco.

[16] Strayed's first book, the novel Torch, was published by Houghton Mifflin Harcourt in February 2006 to positive critical reviews.

Strayed's second book, the memoir Wild: From Lost to Found on the Pacific Crest Trail, was published in the United States by Alfred A. Knopf on March 20, 2012.

[19] The week of its publication, Wild debuted at number 7 on the New York Times Best Seller list in hardcover non-fiction.

[20] The next month Wild reached number 1 on the New York Times Best Seller list, a spot it held for seven consecutive weeks.

[21] The paperback edition of Wild, published by Vintage Books in March 2013, spent 126 weeks on the New York Times Best Seller list.

The book has also been a bestseller around the world—in the UK, Germany, Australia, Brazil, Spain, Portugal, Denmark and elsewhere, and has been translated into 37 languages.

Three months before Wild was published, actress Reese Witherspoon optioned it for her production company, Pacific Standard.

[24] The film was a box office hit, grossing $52.5 million, and led to Academy Award nominations for both Witherspoon and actress Laura Dern, who played Strayed's mother.

The book debuted in the advice and self-help category on the New York Times Best Seller list at number 5 and it has also been published internationally.

In November 2022 a tenth anniversary edition of Tiny Beautiful Things was published with six additional columns and a new preface by Strayed.

[29] In 2017, she taught a writing workshop to students at BlinkNow Foundation's Kopila Valley School in Surkhet, Nepal; the conversations she had with girls at the school led her to make a short film on the topic of chhaupadi, a form of menstrual taboo which prohibits Hindu women and girls from participating in normal family activities while menstruating.