People have lived in the Stretton Gap (or Dale) for thousands of years; an Iron Age hillfort on Caer Caradoc overlooks the town. The name "Stretton" is derived from the Old English words "stræt" meaning "Roman road" and "tun" meaning "settlement"; a Roman road, Watling Street runs through the Stretton Gap, though the town (and adjacent settlements) were not historically located on this road – during the "Dark Ages" the settlements grew a short distance away from the old thoroughfare, for defensive purposes. Today the modern A49 road, which was constructed on its current alignment through the Stretton Gap in the late 1930s, runs along a similar course to the Roman Road. The Roman road was historically known as Botte Street.