Then & Now 1920-2022 The Bridge of Sighs, Chester. A footbridge over the sandstone cutting of Chester Canal. Built in the late 1700s, it was used to take prisoners from the Norman built dungeons at the City gaol to the former Chapel of St John in the south wing of the Bluecoat School. Here they could make their peace with God and receive their last rights before being led back across the bridge for execution. The narrow bridge originally had iron railings to prevent any convicts from leaping into the water below, and was deemed safer than taking them through the streets, where it would be easier for them to escape. City dwellers could stand opposite at the main gate to the city known as Northgate, to witness the felons make their final walk.