Roman villas were built in the area around Winchcombe. Anglo-Saxon tribes called the Hwicci settled the Severn Valley. Winchcombe became the chief city of Mercia under King Offa.
Winchcombe Abbey (Benedictine) founded and completed in 811.
Vikings reached Winchcombe and caused considerable damage to the Abbey.
In 969, during the Benedictine revival, Oswald, bishop of Worcester, compelled the secular clerks who were then dwelling at Winchcombe to withdraw. In their place he put monks to keep the strict rule of St. Benedict, as it was then observed at Fleury, and appointed Germanus, dean of Ramsey, as their abbot. On the death of King Edgar there was a revulsion of feeling in Mercia in favour of the secular priests who had been ousted. In 975 the monks of Winchcombe were expelled and returned to the monastery at Ramsey from which they had come.