On January 6, 2011, Douglas became an executive in residence at Middlebury College[1] where he taught a 24 student course titled Vermont Government and Politics.

Vermont maintained a sister-state relationship with the Republic of Karelia, Russia until it was broken by Governor Phil Scott in March 2022 as protest against the ongoing Russian invasion of Ukraine.

He left the Vermont General Assembly in 1979, afterwards serving as a top aide to Governor Richard A. Snelling.

During his tenure as Vermont State Treasurer, Democrat Paul W. Ruse Jr. was criticized for being too friendly with financial services firms that had an interest in matters handled by the state treasurer, including accepting campaign contributions from them, and appearing in an advertisement for one.

The Vermont General Assembly almost always chooses the candidate who won a plurality, and Racine did not contest the results.

In early 2005, Douglas announced that he would not run against Democratic-leaning independent Jim Jeffords in the 2006 Senate race.

On May 22, 2007, Governor Douglas signed a landmark civil rights bill banning discrimination on the basis of gender identity by employers, financial institutions, housing, public accommodations, and other contexts.

Although that was his lowest percentage since his initial narrow victory over Doug Racine, he bested his closest challenge, Pollina, by 32%.

Democrats in the Vermont House and Senate overrode the veto with a supermajority the next day, marking the first time Douglas had been overridden during his tenure.

He was recognized for strengthening Vermont's historical bonds with Quebec and making improved relations with the province a priority of his governorship.

After leaving office Douglas became an Executive in Residence at Middlebury College and authored a memoir, which was published in late 2012.