Cheryl Strayed

Cheryl Strayed travel, fiction, and memoir author who was born to Ronald Nyland and Barbara Anne his wife in Spangler, Pennsylvania. While she is best known for her writing, it was in 2012 that it was revealed that she was the columnist behind Rumpus’ “Dear Sugar” advice column. She started working there in 2010 when she was requested to take over from legendary contributor Steve Almond who recommended her for the job.

The best place to start is The Best American: Travel Writing series, the earliest of Cheryl Strayed's multi-book series: it opens with The Best American Travel Writing 2000 (2000) and runs to 12 books across 2000–2021, ending with The Best American Travel Writing 2021 (2021). Cheryl Strayed's other series stand alone, so they can be read in any order.

Cheryl Strayed has 40 books catalogued in this guide, published between 2000 and 2024. 30 of them belong to 3 named series — the largest being The Best American: Travel Writing series with 12 books — and 10 are standalone titles, collections or anthologies.

Read each series in publication order — the numbered entries in each series follow the year each book first appeared. Cheryl Strayed's series do not depend on one another, so they can be started in any order; by start date they are The Best American: Travel Writing (2000–2021, 12 books) and Out Of Line (2020, 7 books).

This guide splits Cheryl Strayed's 40 books into 3 named series and 10 titles that stand alone or appear only in collections: The Best American: Travel Writing (12 books, 2000–2021); Out Of Line (7 books, 2020); The Best American: Essays (11 books, 2011–2021).