Lipton received degrees in philosophy and history from the University of Vermont. In 1987 he began his daily newspaper career at The Valley News in Lebanon, New Hampshire. From 1989 to 1994, he worked at The Hartford Courant. While writing for The Courant, he won the 1992 Pulitzer Prize for Explanatory Journalism alongside another journalist for their story about the flaw in the main mirror of the Hubble Space Telescope.