Woolfe studied at
Princeton University.[1] Although he "had written a little bit for newspapers in college", he had not anticipated a career in journalism.[2] In 2008, however, a friend at The New York Observer asked Woolfe to assist in coverage of the
2008 US Open tennis tournament.[2] After additional writing for the paper, Woolfe was offered a regular column in 2009, devoted to opera.[2]
In 2011 Woolfe started working as a freelance music critic for The New York Times, reporting on opera festivals in the US and internationally. In 2015 he became classical music editor, before being appointed as
chief classical music critic in 2022.[3][2][4][5]