-October 1: Peter Shumlin is elected for his second term as Speaker of the Vermont House. Shumlin would later become the 81st Governor of Vermont, serving from 2011 to 2017.
-November 5: Howard Dean is elected Governor of Vermont. Dean, a Democrat, served as governor until 2003. He later ran for president of the United States in 2004, but withdrew from the race before the primaries.
-Vermont passes the first-of-its-kind civil unions law, which grants same-sex couples the same legal rights and responsibilities as married couples. The law was signed by Governor Dean and went into effect on July 1, 2000.
-Ben & Jerry's Ice Cream, headquartered in Waterbury, Vermont, is sold to Unilever for $326 million. The company was founded in 1978 by Ben Cohen and Jerry Greenfield.
-The Vermont Catamounts men's basketball team advances to the NCAA Tournament for the first time in program history. The team, led by coach Tom Brennan, defeated Drexel in the first round before losing to eventual champion Kentucky in the second round.