Windsor County is one of several Vermont counties created from land ceded by the State of New York on January 15, 1777, when Vermont declared itself to be a distinct state from New York.

[3][4][5] The land originally was contested by Massachusetts, New Hampshire, and New Netherland, but it remained undelineated until July 20, 1764, when King George III established the boundary between Province of New Hampshire and Province of New York along the west bank of the Connecticut River, north of Massachusetts and south of the parallel of 45 degrees north latitude.

Joseph Smith, Jr., founder of the Latter Day Saint movement, was also born in Windsor County.

28.10% of all households were made up of individuals, and 11.10% had someone living alone who was 65 years of age or older.

In 2007, the census department estimated that Windsor had the oldest average age in the state, 44.7.

[16] As of the 2010 United States Census, there were 56,670 people, 24,753 households, and 15,420 families living in the county.

[19] Since Vermont began using the popular vote in presidential elections in 1828, Windsor County has voted for the statewide winner in every presidential election in the state's history with the exception of 1912 when it voted for Progressive candidate Theodore Roosevelt over statewide winner William Taft.

Mirroring the politics of the state as a whole, Windsor County was solidly Republican from its inception in the 1856 election until the 1980s, voting only for Democrat Lyndon Johnson in 1964 when he faced the highly conservative Barry Goldwater.

As a result, the Windsor County Sheriff's Department wrote 2,452 tickets in 2007.

[22] Villages are census divisions, but have no separate corporate existence from the surrounding towns.