ePrivacy and GPDR Cookie Consent by Cookie Consent
Skip to content
Illustration of a Highwayman

Illustration of a Highwayman

Photo: Edgar Alfred Holloway, Public domain, via Wikimedia Commons

Highwaymen of Shotover

25 May 2021 (Updated 7 September 2021)

Many centuries ago, before the A40 dual carriageway was dreamed of, the main road leading out of Oxford in the direction of London was Old Road, the path that crosses over the top of Shotover Hill.

Leading through the dense Shotover Forest, this spot was notorious as a haunt of highwaymen looking to steal money and goods from unwary travellers.

There are a number of stories of robberies that took place in this remote spot. In some of these the highwayman involved gets extremely lucky, in others, it is their victim who gets away relatively unscathed.

John Cottingham gets rich

In 1660 a 20-year-old would-be highwayman by the name of John Cottingham stopped a coach carrying army supplies from London to Oxford. John found himself outnumbered four to one by soldiers, but luck was on his side.

The soldiers thought that nobody would be mad enough to try and rob an army coach single-handed, and assumed he must have a gang of accomplices lurking just out of sight in the trees. The soldiers fled, leaving John free to pocket a reported £4000!

Charles Wesley outwits a highwayman

Another story concerns the Methodist leader Charles Wesley, who was travelling alone across Shotover Hill in October 1737. His horse went lame and as night fell he began to fear for his safety.

Sure enough, a highwayman appeared and demanded all his money. Wesley handed over a few halfpence from one pocket, but the highwayman demanded to know if Wesley was carrying any more money.

Reluctant to admit that he had more money but not wanting to lie, Wesley instead told the highwayman to check his pockets himself and see. The highwayman took this as a way of saying that he had no more money and rode away.

In fact, Wesley had a purse in his other pocket containing thirty shillings!