Winterbourne and the surrounding area had an eventful Civil War. Donnington Castle was damaged by cannon; the First and Second Battles of Newbury were fought nearby. On 26 October 1644, Cromwell stayed the night in the Blue Boar public house in the north of the parish and his forces camped at North Heath. In July that year, his forces had taken on Prince Rupert and company at Ripley in Yorkshire, during which successful (for the Parliamentarians) skirmish, they stole a statue of a wild boar that Lord Ingleby had brought back from Italy as one of a pair. The other remains in Ripley Castle. The blue boar was left at the pub. The pub is now The Crab hotel.