- Involved in athletics as a kid, first with his elementary school's basketball team and then with his high school's track-and-field team, placing third at the 1958 New York City indoor one-mile race.
- Came in last in a three-way race for student-body president while in high school.
- Moved to Vermont in 1968, where he supported himself through carpentry and freelance journalism. A decade later, he co-founded a company that produced educational filmstrips for schools.
- Produced a documentary about union leader Eugene V. Debs that aired on Vermont public TV in 1979.
- Ran for statewide office four times (twice for governor, twice for U.S. Senate) during the 1970s, but lost each race. It wasn't until he ran for mayor of Burlington in 1981 that he enjoyed success at the ballot box—and that was by a 10-vote margin. He was re-elected, by much wider margins, four times.
- First elected to the U.S. House of Representatives in 1990. He was re-elected seven times; and then sought and won a seat in the U.S. Senate in 2006.
- Released a cassette-only album in 1987 titled We Shall Overcome. One side featured folk songs, including "Where Have All the Flowers Gone?" and "We Shall Overcome"; the other side featured "A Conversation With Bernie Sanders." It sold about 1000 copies in Vermont at the time.
- Sought to be the Democratic Party's nominee for President in 2016, but lost out to Hillary Clinton.