| Famous Alumni | |
- Vanessa Branch – Miss Vermont, spokesperson for Orbit gum
- Jim Douglas – elected to the Vermont House of Representatives the same year he graduated from Middlebury; he is the former governor of Vermont.
- Roger Easton – developed TIMATION, on which the current GPS is based on. He was inducted into the National Inventors Hall of Fame in 2010.
- Donald M. Elliman, Jr. – director and executive VP of Time Inc. from 1995 to 1999. He was also president of Sports Illustrated from 1992 to 1998.
- Eve Ensler – playwright of "The Vagina Monologues"
- Ari Fleischer – former White House press secretary, was the primary spokesperson for President George W. Bush
- Ann Jackson – the founding publisher of InStyle magazine and has held numerous distinguished positions at different well-known magazines such as Real Simple, Money, Sports Illustrated, and Time, Inc. publications
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