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St. Andrews Jail was built in 1832 of huge granite blocks brought over by boat from Deer Island, the Town not having had a quarry at that early date. The new jail replaced the original structure, which stood at town center on the site of the current Town Hall, and which in 1842 was converted to the Market House. There were complaints about the jail as soon as it was built. The wind blew through the cracks and in one celebrated instance the jailer's goose froze.In the old days the Jail was usually managed by a husband and wife team who lived there and took care of feeding the prisoners. The name of the first jailer was Captain Snow. His wife died there in 1834 after she fell asleep at the fireplace and her clothes caught fire. St. Andrews was the Shiretown for Charlotte County, which meant that justice was administered for the County here. This included several executions. The first execution was at the old Jail and Courthouse, located at the current Town Hall site, in 1826. The new jail saw the execution of Thomas Dowd in 1878 and Roland Hutchings in 1942. This was the last execution in the Town. The jail continued in operation until the 1970's. Residents remember how "prisoners" would be given freedom for the day to go swimming or almost whatever they chose, so long as they were back in their cells by curfew.
There have been a number of daring jailbreaks over the years. The Old Jail also had a debtor's section on the upper floor.
For the last few decades the Jail has been the home of the Charlotte County Archives, and a common stopping point for tourists who can still view the forbidding cells that give a sense of life in the immediate post-Loyalist days.