Deadman's Riding is a track that winds its way along the northern edge of Ditchley park. It also lends its name to Deadman's Riding Wood to the south, and both are recorded on maps dating back to at least the mid-19th century. The origin of the name is lost, but similarly-named paths got their name due to their use as a route for coffins being transported to a church for burial, such is the case with Dead Man's Walk in central Oxford.

Deadman's Riding heads in a north-westerly direction, towards the Hoar Stone near Enstone. According to Katherine Briggs, some believe that the Hoar Stone marks a grave or burial site, and that Deadman's Riding is so-called as it was the route used to transport the body there for burial.

In Folklore of the Cotswolds, Briggs also records the 1973 account of Mr. Abbott, 'a septuagenarian of Fulwell', who claimed to have been walking along Deadman's Riding when he witnessed the ghosts of two men drifting along the track before passing straight through a wire-netting fence, much to the distress of Mr Abbott's dogs who 'crouched and bristled and would not move until the ghosts had passed'!

The grand manor house at Ditchley Park had its origins as a royal hunting lodge, providing accommodation for nobles enjoying terrorising the local Wychwood wildlife. In the Elizabethan era, the land was sold to Elizabeth's favoured courtier Sir Henry Lee, who is responsible for the first iteration of the grand house and parkland that can be seen at Ditchley today.

One charming local legend relates to Sir Lee's mastiff Bevis, who was a not particularly favoured pet until one night when he truly earned his place at his master's side. On the night in question, Bevis stubbornly refused to leave his masters bedchamber, and despite being turned out a number of times he kept returning to his masters bedside. Eventually Sir Lee gave up and allowed the dog to stay, and was glad that he did.

In the middle of the night Sir Lee was woken by Bevis growling loudly before flinging himself onto and overpowering a dark figure who had crept into the bedroom. The intruder turned out to be Sir Lee's valet, who confessed that he had intended to murder his master while he slept in order to rob him!

Sir Henry Lee showed his gratitude for his loyal dog by having a grand portrait painted of him with Bevis by this side, which is said to have hung in the hall for over 300 years.

Ditchley takes its name from Grim's Ditch, a stretch of bank and ditch earthworks that crossed the park from the north east to the south west. The earthwork which shares its name with a large number of similar ditches throughout England. 'Grim' is an Anglo Saxon term used frequently to describe things of an unexplained or mysterious nature, indicating that our Anglo Saxon ancestors were none the wiser than we are about the purpose that these ditches once served!

More intriguing still is 'Devil's Pool', a pond to the south of Ditchley Park which can be found marked on 19th century maps. I've not been able to confirm the origin of the name, but I suspect it is connected to Roman remains, including a stretch of tessellated Roman flooring, that have been found nearby.

It was not uncommon for locals to attribute suspiciously man-made yet unexplainable features of the landscape, such as earthworks, standing stones and similar constructions to the work of the Devil and the same thing may apply here. The name may also have been borrowed from Devil's Pool Bottom, a pond found a few miles away in the Wychwood forest near Finstock.

The land around Ditchley Park was once home to not one but two of Oxfordshire's many lost medieval villages, with the site of the village of Ditchley to the south and the lost village of Asterleigh to the north. Asterleigh had a church with adjoining churchyard, now only visible as a rectangular earthwork.

The location of Asterleigh and its church at the southern end of Deadman's Riding could lead one to speculate that at one time the route may have been used to transport bodies south to Asterleigh church rather than north towards Fulwell, Enstone and the Hoar Stone.