An incumbent governor of Vermont has not been defeated for reelection since 1962, when Democrat Philip H. Hoff beat Republican F. Ray Keyser, Jr. by 1,315 votes.

[8] Shumlin announced in December 2013 that he was running for reelection to a third term in office, but said that he would not begin campaigning until after Labor Day 2014, just two months before the election.

Its members discussed challenging him in 2014 because of his proposed cuts to social programs, but the party openly admitted that it lacked the money for a gubernatorial campaign, and no candidate came forward to run.

[28][29][30] Peter Diamondstone, who co-founded the Liberty Union Party and has run for elected office almost two dozen times, was unopposed.

[22] A general election debate, attended by party nominees Shumlin, Milne, Diamondstone and Feliciano and Independent candidates Ericson, Peters and Peyton, was held on October 9.

It attracted considerable media attention and was described variously as "funny", "strange", "crazy", "one of the strangest of this election cycle", "very, very special" and "beard-filled".

[33][34][35][36][37][38][39] Comments by all of the candidates apart from Shumlin drew media attention and laughter from the studio audience,[33] such as Milne describing himself as "third-generation, born in Vermont", only to correct himself and state that he was born in Brooklyn;[33] Ericson, who sported a large bow-topped hat, suggesting that poor Vermonters use their food stamps to buy lottery tickets[33] and decrying "chemtrails";[35] Diamondstone, who wore jean shorts with suspenders and long socks and sported a large beard, calling for revolutionary socialism, the legalisation of all drugs[35] and secession from the union,[36] as well as comparing students to "slaves" because of the cost of higher education[37] and responding to a question about the Department of Children and Families by railing against the U.S. military and the "Zionist regime";[37] Peters answering a question about the affordability of college in Vermont by saying that he had "no idea";[35] and self-described "light worker" Peyton[35] shouting at Shumlin for allegedly closing highway restrooms[37] and using her closing remarks to ask Vermonters if they'd rather choose money or love.

[39] Former governor Howard Dean described the debates as a "good thing for the state"[39] and Time magazine's Denver Nicks called them a "breath of fresh air" and "pure entertainment".

[40] Of Vermont's 275 "polling places" that report results separately—corresponding to the state's 255 towns and cities, with some larger municipalities broken into multiple precincts—Milne won a plurality in 162 precincts, or 58.9%.

[53] The Assembly most recently reversed a plurality vote in the 1976 lieutenant gubernatorial election, when the Republican-controlled legislature picked Republican T. Garry Buckley rather than Democrat John Alden, who was suspected, and later convicted, of insurance fraud.

"[60] As 91 votes are needed to elect the governor from the 180-member body and Democrats and Progressives held 112 seats, it was considered unlikely that Milne would win.

"[67] On December 8, Milne held a press conference in which he defied suggestions that he would concede by officially announcing that he was asking state legislators to vote for him.

Shumlin, who had missed two earlier financing deadlines, said that "this is not the right time" because the federal government had offered less funding than expected and "the potential economic disruption and risks would be too great to small businesses, working families and the state's economy.

"[70] The media also cited controversy surrounding comments made by economist Jonathan Gruber, who was involved in crafting and advocating for the plan, and Shumlin's failure to win a majority in the election as reasons for the cancellation.

[72][73] Business groups lauded his "pragmatic" move but supporters of health care reform organized protests and said that it would end his political career.

[74][75] At the end of December, the newly formed group "Vermonters for Honest Government" raised $30,000 to air television advertisements aimed at pressuring legislators to vote for Milne.

The group's founder, retired United States Navy Captain Bill Round, said that legislators should vote against Shumlin because "he's promised a lot and failed to deliver.

"[80] Shumlin said that if Milne were to win, Vermont would be "paralyzed", as the new administration lacked the time needed to assemble a new staff and draft a budget for the 2016 fiscal year.

He also offered his support for amending the state constitution so that as long as a plurality winner received at least 40% of the vote, the Assembly would not be required to decide the election.

[82] As no candidate received a majority of the vote, the Vermont General Assembly was required to decide the election, choosing among the top three vote-getters, Shumlin, Milne and Feliciano.

The Burlington Free Press speculated that Feliciano drew voters dissatisfied with Shumlin but who would have voted for Milne if they had realized that he had a chance to prevail.

[89] A Feliciano campaign consultant felt, based on polling, that her candidate's stance against Shumlin's healthcare policy garnered votes.

[51] University of Vermont political science professor Garrison Nelson said that "the people who showed up are the angry ones" and that, unlike Shumlin, "Welch demonstrated an appeal far beyond just the Democratic base.

He also pledged to move ahead with single-payer health care and to address school spending, property taxes and the $100-million budget gap.

Several candidates announced their intention to run: for the Democrats, former state senator and 2010 gubernatorial candidate Matt Dunne,[93] former secretary of the Vermont Agency of Transportation and former state representative Sue Minter[94] and Speaker of the Vermont House of Representatives Shap Smith;[95] for the Republicans, retired banker Bruce Lisman[96] and Lieutenant Governor Phil Scott.