Cymbeline’s Castle, jutting out from the Chilterns escarpment, sounds like an intriguing place. Could it be the site of one of the great battles for Britain, where the first century King Cunabelin (also known as Cymbeline) fought off the invading Roman hordes?

I set off from Princes Risborough to find out, with friends who had been inspired by an article in Walk, the Ramblers magazine, about the ‘Outer Aylesbury Ring’, which must be just about the most uninspiring name possible for a long-distance path.

The 53-mile path was created as a larger circle outside the 32-mile Aylesbury Ring footpath to “link plenty of big views and explore the pretty villages around Aylesbury”.

The magazine tempted us with the promise of “riotous wildflower displays” and red kites soaring over the neon-green beechwoods. It seemed unlikely that we would see bright flowers in winter, but the kites are a permanent feature and we hoped the ground would glow with a golden carpet of leaves.

One of the most picturesque sections of the ring starts from Princes Risborough along the Ridgeway. The 5,000-year-old drovers’ trail is dotted with hill forts and tumuli because our ancestors also walked in search of big views — to spot enemy armies rather than to admire the countryside.

The trail climbs Whiteleaf Hill, which dates from Neolithic times. The most visible artefact is more recent — trenches apparently dug by First World War soldiers practising before leaving for the battlefields of France.

War poets mired in the mud often longed for home, focusing on memories of the landscape they loved.

Before the war, Rupert Brooke joined Robert Frost on long Chilterns walks, and wrote of “the white mist about the black hedgerows”, taking “the Roman road to Wendover” to recover from a failed love affair, and his later poems often reflect on quintessential England.

The ancient Whiteleaf Cross, whose origins are shrouded in mystery, was impossible to see from the top — and indeed from close up, since grass has grown over the chalk carving.

Our route forked east, dipping through slippery chalk paths down to the Plough at Lower Cadsden, a pub which briefly featured in the news when Prime Minister David Cameron, MP for Witney, accidentally left his daughter behind. Like many Chilterns inns, it is more of a restaurant than a pub, with only a few bar stools for those in search of a quick drink rather than a three-course meal.

We shivered in the garden, quickly downing our crisps and lemonade, before continuing along lanes and fieldpaths to Chequer’s Knap. There was no sign of Chequers itself, the country residence of Prime Ministers since 1921.

From here, the Ridgeway veers south to give walkers a great view of the 16th-century mansion’s intensive security features, installed in the last few decades after a brief suggestion that the ancient right of way might have to be diverted.

We did not go that way, but instead took the Outer Aylesbury Ring, which follows a northerly route towards the pretty village of Ellesborough, via Beacon Hill, where — with difficulty — we picked out Cymbeline’s Castle, jutting out into the valley. The original British fort was replaced in medieval times by a motte and bailey castle, now almost totally hidden by trees.

Nowadays Beacon Hill is a better viewpoint than Cymbeline’s Castle and we lingered there, enjoying the Vale of Aylesbury laid out before us — and fascinated by the strange site of two men behind us, using ice-axes to ascend the grassy slope.

One was preparing for an expedition to the Alps, while his trainer explained that the steep gradient was perfect for practice sessions. The hill is an open access area, but protected by a security camera. We hoped the watching secret service agents were as amused as we were by the Alpine antics.

As for Cymbeline, could this hill, whose name is reflected in Little Kimble and Great Kimble, have inspired Shakespeare’s play? The plot is convoluted, but the battle clearly takes place in Wales.

However, the writer and actor Julian Dutton has no doubt that the Bard probably passed here on one of his frequent journeys from the Globe to Stratford-upon-Avon. In his book Shakespeare’s Journey Home, Dutton suggests that the legend of Cymbeline “would have exercised a spell over him” when he travelled this way.

Like the war poets, perhaps he was so moved by the beauty of the countryside that it lodged in his mind as the essence of England, a place people would fight to the death to defend.

Dutton believes the sense of landscape and place permeates Cymbeline, just as the blasted heath has resonance in Lear. Shakespeare had “a soul nourished by the old lore of the country, the traditional stories of the shires”.

“To pass through the place where Cymbeline had his camp before battling with the Romans would have had a frisson for him,” Dutton’s book claims.

Plenty of others have attempted to re-create Shakespeare’s journey, but few come this way. The 146-mile Shakespeare’s Way, a popular long-distance footpath, follows the shortest practical route between Stratford-upon-Avon and Oxford, and climbs the Chilterns several miles south at Cookley Green, taking the Thames from Marlow to Shakespeare’s Globe in London.

Another Shakespearean walker was theatre director Dominic Dromgoole, who made the epic journey with friends, reciting sonnets on easy stretches and declaiming tragic epithets when faced with deep mud and unhelpful maps. After encountering the notorious ‘stepping stones’ near Stadhampton, they seem to have crossed the Chilterns at Watlington Hill.

Dromgoole reflects on the contrast between the close, rigid world of the market town of Stratford and the urban life of London’s Tudor actors, but also the countryside in between, filled with superstitious rustics and herbal healers dabbling in magic spells, for whom spritely goblins, flying fairies and woodland robbers were only too real.

Dromgoole says the plays reflect the earthy country life of the time, as well as courtly behaviour.

“Flowers and sheep and willows and brooks are Shakespeare’s sustenance,” he said.

There is plenty of evidence that Shakespeare loved the countryside and spent time studying it. He finds “tongues in trees, books in the running brooks, and sermons in stones”, pictures a “willow grown aslant a brook”, a “bank where wild thyme grows”.

Dromgoole describes the prospect of having to climb the Chiltern scarp after a day’s walk from Oxford. Confronted by: “a county-long wall of raised earth” he reads Mark Antony’s oration from Julius Caesar to distract himself from the pain in his legs.

We felt the same as we left the soft fields of Ellesborough for the ascent of Coombe Hill, which has been improved with wooden steps to avoid the chalky slide which would otherwise face walkers.

After the long climb, it was a relief to join the Ridgeway for the final stretch across a grassy ridge, with the golden globe of the Boer War monument appearing at last on the horizon.

This monument had a brief brush with fame when a Boxing Day rambler took a photo here of the Prime Minister and his wife with Hollywood couple Tim Burton and Helena Bonham Carter.

Apparently, Mr Cameron has also walked here from Chequers with German Chancellor Angela Merkel, a keen hiker. The view is breath-taking, from Hatchet Hill near Swindon to Dunstable Downs and beyond, but many features are urban, from Didcot Power Station to the sprawl of Aylesbury and RAF Halton. It is difficult to imagine what the landscape would have been like in Shakespeare’s time, before hedgerows were planted by ‘modernising’ landowners.

On the final downhill stretch to Wendover, I am ashamed to say we did not recite Shakespeare from memory. Instead, we reflected on the fatal flaws that eventually trip up great leaders — Caesar, Lear and all Shakespeare’s kings — and how “golden lads and girls” must all eventually come to dust.