Penn's growth in the Middle Ages was probably driven by its position on a major route, connecting not just the local towns of Wolverhampton, Stourbridge and Kidderminster, but the county towns of Stafford and Worcester, and forming part of the main north-south route of Western England. Traffic struggled up and along the ridge, past the hamlet of Ryecroft to Upper Penn. The present route of the A449/Penn Road evolved only in the modern period, with an 18th-century toll road providing a more convenient thoroughfare and bypassing Upper Penn village.