Sheriff D. Michael Chamberlain
Michael Chamberlain, Windsor County Sheriff, started his career in law enforcement in 1971 with the Woodstock Police Department. After serving four years with that agency as a patrolman,
Sheriff Chamberlain was hired by the Windsor County Sheriff's Department where he spent four years as Chief Deputy. In 1979, Sheriff Chamberlain was elected Sheriff for Windsor County and
served in that position for sixteen years. In 1995, Sheriff Chamberlain chose not to run for re-election and spent the next four years working in the private sector and with several other law enforcement agencies.
In 1999, Sheriff Chamberlain was elected a second time as Sheriff for Windsor County and has been serving in that position to present. He has served forty one years in law enforcement,
thirty of those as Windsor County Sheriff.