Chester was created, with the name Flamstead, by a New Hampshire charter granted 22 February 1754 by Governor Benning Wentworth. It was the first town created in what is now Windsor County. This charter was forfeited due to the proprietors' failure to meet its terms.
A second New Hampshire charter was granted 3 November 1761, with the town called New Flamstead. New York created Cumberland County 3 July 1766, including New Flamstead with all of the other New Hampshire Grants east of the Green Mountains. This was annulled in 1767 by Royal decree, and passed again in 1768. A third charter was granted 14 July 1766 by New York authority, and the town was renamed Chester.
The citizens of Chester drafted one of the first declarations of independence in America, 10 October 1774. It stated, "that all the acts of the British Parliament tending to take away Rights of Freedom ought not to be obeyed." (From "The Vermont Book of Days", 10 October 2004, www.vtbookofdays.com)