Formed February 16, 1781 (3rd county)
Windsor County (57,751), Woodstock (937)
The traditional Greek Revival red brick courthouse was constructed in 1855. It is located on Court Street at Park Street. United States Highway 4 is Park Street in the town. Thomas W. Silloway provided the designs. There is 1990 supporting Courthouse in Wind River Junction. The county was founded on February 16, 1781 from Bennington County as the 3rd county with Woodstock as the only county seat. Windsor County is named for Windsor, Connecticut. The county seat is reportedly named for Woodstock, England. Windsor County is the birthplace of 8 Vermont Governors, Horace Eaton, Carlos Coolidge, Ryland Fletcher, Redfield Proctor, William W. Stickney, Fletcher D. Proctor, Redfield Proctor, Jr., and Mortimer R. Proctor.
Windsor County government consists of a sheriff and 2 Assistant Judges. One Superior Court Judge serves Windsor, Caledonia and Windham counties, One Superior Court Judge serves Windsor and Orange counties, and Three Superior Court Judges serve Windsor County. The county is located on the eastern border with New Hampshire. The Connecticut River forms its eastern border. Burlington, Vermont is northwest and Manchester, New Hampshire is east of the county. The county center is 10.8 miles Southwest of Woodstock nearer Reading. The county is surrounded clockwise by Orange County and New Hampshire and Windham, Bennington, Rutland, and Addison counties.
The area of the county is 971 square miles. It is 1 out of 14 in the state. It ranks 4 out of 14 in population in the state. It has a density of 59.5 persons per square mile making it 6 out of 14 in the state. Windsor County has 3.0% of its population in its incorporated areas. Interstate Highway 89 originates in the county and goes northwest into Washington County. Interstate Highway 91 passes north to south from Orange County to Windham County. United States Highway 4 crosses east to west from New Hampshire to Rutland County. United States Highway 5 parallels Interstate Highway 91 from Orange to Windham counties. Calvin Coolidge, the 29th President, was born and is buried in this county. The county is a fat capital letter J. Woodstock is located in the eastern third of the county. Woodstock is the county seat and the largest city. It is 1.6% of the county population. This county is in the Lebanon Micropolitan Statistical Area.
Ludlow
Perkinsville
Woodstock