Between the treetops, I can see the towers of a distant mist-shrouded castle. Is it possible I could make contact with the spirit of the great Welsh hero Owain Glyndŵr so soon, at the very start of our hike? We are not even on the actual trail of Glyndŵr’s Way. I’ve had to make a detour to find accommodation that takes dogs, as Stevie the terrier is with me. The Castle Inn at Knucklas is a mile off the route, and two miles or so from the pretty border town of Knighton – where the 135-mile (217km) Glyndŵr’s Way officially begins.

The towers slide away behind trees and a railway viaduct emerges. The medieval castle ruins, it turns out, are believed to have been plundered to build the viaduct in the 1860s, and the builders dropped in a couple of crenelated towers to honour the origins of the stone. I fear this may be an early omen: the spirit of Glyndŵr will be as elusive as the man himself was in his lifetime.

After his great rebellion of 1400 devolved into a murderous guerrilla campaign, the last Welsh prince of Wales simply disappeared. His English adversaries thought he had supernatural powers. Writing two centuries after the events, Shakespeare has Glyndŵr declare (under the anglicised name Owen Glendower) in Henry IV: Part I that “the earth did shake when I was born” and “I can call spirits from the vasty deep”. The last known sighting was in about 1819, when William Blake saw him in a vision and sketched his gaunt head. Since then, nothing. If he’s been hard to pin down for six centuries, what chance now?

Welsh rebel leader Owain Glyndŵr seen in battle in a painting by AC Michael. Photograph: Lordprice Collection/Alamy

I plan to cover the 75-mile southern section of the national trail’s great horseshoe across mid-Wales, starting with a late afternoon two-mile warm-up from Knighton station up to Knucklas. On our first full day of walking, we head south out of Knucklas and soon reconnect with the main path. The hills are bone dry, lying like dead giants across our route, defended by armies of sheep. Stevie is nonchalant. He was born near Rhayader and is good friends with a tup called Patrick. Nevertheless, I keep him on a tight leash.

The rebellion started with a land theft, an English lord helping himself to some of Glyndŵr’s hectares, a personal feud that laid bare a vast hinterland of Welsh disgruntlement. Men flooded back from England to join Glyndŵr. Edward I’s great fortress at Conwy was captured; a battle near Knighton was won. It was all going well until the teenage son of Henry IV (the future Henry V) was put in charge of the English forces. Not for the first time, British history turned on an arrow: this one burying itself six inches into the young Henry’s skull at the Battle of Shrewsbury. He survived. The rebellion faltered.

It is coming over Bailey Hill that Stevie gets the first hint of danger. A flock of sturdy old ewes spot him and form a tight huddle, a testudo formation, to slink up behind us. Stevie turns and does a comedy backwards leap of surprise. The ewes stamp their feet. Stevie hides behind a tussock. The ewes creep forward. I pull him through a gate. He has not barked or rushed at them. He has done well. Soon, we drop down into the hamlet of Llangunllo, where there is a pub. “It’s closed,” says a local woman. “Evenings and weekends, and for drinking only.” There is a dearth of facilities along Glyndŵr’s Way, widely considered the most remote of all 17 English and Welsh national trails, and I have brought a stove and teabags. This will prove a good decision. We set off up the lane and then on to the hills. It is quiet, very quiet. Nothing moves except the distant wind turbines.

The writer on remote Glyndŵr’s Way. Photograph: Kevin Rushby

Rebellion is in the air at the moment. The Uprising, a film about the 1381 Peasants’ Revolt, directed by Paul Greengrass, will be released in the UK on 9 October. And a new play by Gary Owen, Owain & Henry, opens on 5 November in Cardiff with Michael Sheen in the lead role. On a call before I set off, I ask Sheen why Glyndŵr remains such a potent hero. “His vision for a Welsh nation was based on a Welsh parliament, universities, religion and the laws of Hywel Dda,” he tells me. “It’s a vision that resonates. The play feels like a conversation between then and now.”

Sheen himself has walked parts of Glyndŵr’s Way. He says: “Owain could only do the uprising because of that landscape; it enabled a guerrilla war and you still feel that today.”

Stevie and I take a break in the Llangunllo bus shelter. There are no refreshments, but there are stacks of unwanted books. I find a copy of Francis Kilvert’s Diary, by the Victorian curate who kept a vibrant record of life in the Welsh borders. “Who died on the cross to save us all?” he asks one wild child from a remote Welsh farm. “Lord Chesterfield,” she replies. I tuck the book in my pocket.

Approaching the hamlet of Llangunllo. Photograph: Simon Whaley Landscapes/Alamy

Soon we are climbing over hills where the heather and gorse is in glorious bloom and there are no roads except droving tracks. These green lanes were once used to send cattle and sheep across the border, a tough, brawling existence hinted at in Kilvert’s Diary. By then, however, the railways had arrived and the old droving life was doomed.

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At our first encounter with cattle, Stevie is happy to be carried. Different breeds, we soon learn, represent different threats: big cows can’t be bothered, small feisty ones are to be avoided. We take some long detours.

Our second night is at Brandy House farm, a welcoming place with various types of accommodation. We choose the vintage caravan. Nearby Felindre has a simple pub, the Wharf Inn, serving one of my favourite beers, Wye Valley Brewery’s Butty Bach.

Now the walk really begins to deliver. Majestic upland stages pass epic locations such as the Castell y Blaidd, the castle of the wolf, before arriving at Abbeycwmhir, the abbey that Glyndŵr reputedly sacked. I’m staying in a cabin at Wales in the Woods, a couple of miles up the hill in a deep, silent pine plantation, perfect for Glyndŵr reflections.

The ‘lovely, eccentric’ town of Llanidloes. Photograph: Joe Dunckley/Alamy

Next day, rain threatens, but we dodge all the showers, passing Saint Harmon, where Kilvert was briefly vicar, enjoying a stop at the superb Welsh Mountain Cider, then dropping down to Llanidloes. After three days on the trail, this lovely, slightly eccentric town seems like the big city, with so many pubs to choose from. We stay at the Unicorn. The following morning, we pass the Clywedog dam and climb to Y Star Inn, one of the highest pubs in Wales, which has three smart new pods to stay in. From here, the path rises again on what, for me, is the greatest stage of all. Leaving the trail, Stevie and I climb the 564-metre hill of Foel Fadian, opening up great panoramas of Cadair Idris, Yr Wyddfa (Snowdon) and the Irish Sea. We follow the trail down and reach our destination, Machynlleth, a town that has the same eccentric edge as Llanidloes, with lots of interesting independent shops, pubs and cafes.

It was in Mach (as the locals often call it) that Glyndŵr briefly set up his parliament, and the building, albeit partially reconstructed in 1460, survives. It is an atmospheric spot and there, on the wall, charging into battle, is the great hero himself. Now I get the ghostly shivers. But it turns out the Victorian artist used the face of his patron, David Davies, the indefatigable railway builder of the 1850s and 60s. After five days of walking, Owain has eluded me yet again.

The trip was provided by National Trails and Natural Resources Wales. Walking Glyndŵr’s Way by Paddy Dillon is published by Cicerone (£16.95). To support the Guardian, order your copy at guardianbookshop.com. Delivery charges may apply.

Owain & Henry runs from 5-28 November at Wales Millennium Centre, Cardiff

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