The old village jail traveled many miles after its construction in the late 1800's. It began in the Bell Tower Building on the south side of the alley off Riley Street, then was moved across the alley to the new Dundee Village Office on Riley Street in the 1990's. Because two people could lift the jail and allow one person to escape, officials could not place more than one person in it at a time. Stories about it include four inebriated farmers who were locked up for the night; in the morning, one needed to go milk his cows, so the other three lifted the jail for him to escape, and he returned after milking. Mike Yeck procured and refurbished the jail for use during the 1974 sesquicentennial, when it was filled with loved ones and "arch enemies" taking part in the celebration, and it also traveled to nearby towns to advertise the fun in Dundee. From 2001 through 2021, the Monroe County Sheriff's Department used it as an exhibit at the Monroe County Fair, and in August 2021 it returned to Dundee's Old Mill Museum.