Windsor County is situated in southeastern Vermont above Windham County. Windsor County is Vermont's largest County in size at 977 square miles. Vermont history has recorded that counties were set and defined by the needs of a Probate District according to growth and population. This resulted in multiple probate districts. In 1779 there were four probate districts in Cumberland County (Guilford, Rockingham, Windsor and Barnet). In 1781 Cumberland County was abolished and the counties of Windsor, Windham, and Orange were formed. Windsor County was incorporated on February 21, 1781 and its shire town is Woodstock.
Windsor County is one of several Vermont counties created from land ceded by the State of New York on 15 January 1777 when Vermont declared itself to be a distinct state from New York. 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. New York assigned the land gained to Albany County. On March 12, 1772, Albany County was partitioned to create Charlotte County, and this situation remained until Vermont's independence from New York and Britain.
According to the U.S. Census Bureau, the county has a total area of 977 square miles (2,530 km2), of which 969 square miles (2,510 km2) is land and 7.4 square miles (19 km2) (0.8%) is water. It is the largest county by area in Vermont.
The establishment and election of Sheriffs for their respective district is found in Chapter II "Plan or Frame of Government" Section 50 of the Constitution of the State of Vermont.
Listed are the Elected Sheriffs of Windsor County, State of Vermont to present:
The Sheriff's Department is housed in the old County Jail/State Prison in Woodstock. The Facility no longer hold prisoners. It closed its doors in 2002 and became the home of the WCSD in 2003.
By MATT SMITHWICK RUTLAND HERALD
Southern Vermont Bureau WINDSOR — The prison in Woodstock will finally close its doors Monday, when the Windsor prison begins accepting short-term prisoners in its new holding cells. Officials at the Southeast State Correctional Facility in Windsor met with local law enforcement officials Friday to show the facility’s just-finished holding cells, which can hold up to eight short-term prisoners. A former recreation area at Windsor was converted to holding cells when it was decided earlier this year that Woodstock’s 65-year-old prison would close. The facility in Woodstock stopped housing full-time prisoners in March, but it has been operating recently as a holding cell for those awaiting arraignment. Now Windsor has the capability to temporarily hold those prisoners. “These holding cells are merely to be used for local law enforcement so when they arrest somebody, they don’t have to drive to Rutland or St. Johnsbury,” said William Soule, interim superintendent at the Windsor jail. He said the Windsor facility would serve as the temporary lockup for Windham, Windsor and Orange counties. People arrested in those counties could be lodged at Windsor until they are arraigned. If they must remain in jail after a court appearance, they will be transferred to another facility, Soule said. The Windsor prison’s regular population consists of about 100 inmates. Most of that population is made up of sex offenders, Soule said. The facility is minimum security. The temporary prisoners won’t interact with the general population in Windsor, Soule said. Most stays will be a day or two, with some weekend stays until arraignment on Monday. “These people are only going to be housed here until they go to court and they’re arraigned,” Soule said. The $60,000 renovation job at Windsor was a kind of compromise. When it was announced that the Woodstock Regional Correctional Facility would close, police thought they would have to take prisoners to holding cells in Rutland or St. Johnsbury. Those trips would have driven up overtime and transportation costs, so part of the Windsor jail was converted for temporary prisoners. Officials plan to make use of those temporary cells until the 350-bed medium-security prison in Springfield is completed. The Springfield prison is under construction and is expected to be finished in late 2003. Springfield Police Chief Douglas Johnston attended the meeting Friday at the Windsor facility, and said the holding cells there was a good temporary solution. Taking prisoners to Rutland or St. Johnsbury would have run costs up, he said. The Springfield department uses off-duty officers to transport prisoners, Johnson said, in an effort to keep working officers in town. “It cuts down on travel time.” The Woodstock jail, located in downtown Woodstock, is the oldest and least efficient in the state system, and the cost of housing 75 inmates there is expensive. The original plan was to keep it open until the new Springfield prison was completed. But the early closure is part of the Corrections Department’s plan to save several million dollars over the next two years. Like a number of other law enforcement officials, Johnston says that closing Woodstock prior to the opening of the Springfield prison is a mistake. Fewer prison beds in the state means more people who should be locked up will be walking the streets and committing crimes, he said. “We’re going to pay for it later on because the crime rate is going to go up in the community,” Johnston said.
The Public Works Administration funded the construction of the former Windsor County Jail in Woodstock. The structure was finished in 1936 and it contains the courthouse, cell blocks, and the living quarters of the sheriff. The architect of record was Charles H Crandall of Randolph, Vermont. Docket No. Vt. 1024-R.