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ABOVE: Windsor makes a yardage gain during its game against Lebanon in the shadow of the state prison in Windsor on Oct. 18, 1969. Windsor won, 19-8, as part of an 8-0 season that captured a share of the Vermont Division II title. (Middlebury was also undefeated and shared the state title, which was based at the time on regular season records instead of a postseason playoff tournament.) This year, Windsor is taking on Woodstock in the Vermont Principals’ Association Division III championship on Saturday, and the prison closed for good last week, after 208 years in operation.

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