It all started with a dispute over a bit of land. A rich and powerful foreigner claimed some fields were his, a local was adamant they were not. There had already been other rich and powerful foreigners building holiday homes – whopping great crenellated ones – and when our local hero raised his flag, it all kicked off. The most recent Welsh rebellion was under way. It was 1400.

Our present-day Owain Glyndŵr tour starts in the countryside near Oswestry, where there is a lovely green hill and an oak tree with a small coat of arms nailed to it. “Some say he’s buried under there,” says Rob Laird, our guide on the trail of the Welsh hero, a trail launched this year to mark 600 years since he died. It will take us right across the country, from this border area to Cardigan Bay in the west.

“This was his homestead, a place where they said the door was never locked: bards, storytellers, troubadours – they all came. Glyndŵr was the Prince of Powys and this was his court, really.”

The nearest village is Sycharth and this tranquil spot is where the Glyndŵr story begins, the place where he was living contentedly until the land-robbing started. His rebellion then cut a swath across the country, taking in some of Wales’s most spectacular locations – places that Rob has cleverly woven into a tour. It was the biggest rebellion Wales ever had. “He deserves to be remembered,” says Rob.

We loop north, stopping at Ruthin to take a peek at the castle of Glyndŵr’s enemy, Lord de Grey, the English nob who triggered the rebellion by seizing lands that were not his. De Grey’s home is now atmospheric, peacock-adorned ruins attached to a hotel. Ruthin in those days was a cantonment, an English garrison in hostile territory. Rob is loosening up, starting to get into his stride. Why did Glyndŵr fail? Why did he not become the Welsh William Wallace? Will there ever be a Welsh Braveheart film and independence referendum? We are going to attempt some theories on our journey across the principality.

We jump in the car and head south to Corwen, a gorgeous, neglected little town that deserves to be visited, if only for the graveyard and church, which look like they were built for Gothic television dramas, or maybe a scene in the Welsh Braveheart to come. “I see Rita Ora as the love interest,” says Rob, “Tom Jones as the wise bard, Iolo Goch.” But who to play Glyndŵr?

At Corwen, on 16 September 1400, the Prince of Powys raised his standard and disgruntled Welsh fighters flocked to him. Many, like Glyndŵr himself, had been mercenaries in the English army. On a wall at the back of the atmospheric churchyard there is the imprint of a medieval sword, reputedly Glyndŵr’s. Inside there is an ancient stone effigy of a knight, looking like he has just laid down for a snooze between rousing rebel speeches. I can almost see Tom Jones, striding through swirling mist, past the 10th-century cross and pagan standing stone, growling to camera, “I carry Wales around inside me.”

The wildly eccentric 20th-century novelist, John Cowper Powys, lived in Corwen for many years and was inspired to write his novel Owen Glendower (1942), a book “deep with the half-tones and shadows of the legendary past of Wales”, as one critic put it. Perhaps there’s a screenplay in it. The town also has a statue of Glyndŵr in the High Street, a recent replacement of an older work that was “like a short-arse from the Lord of the Rings,” one local informed me. Now he’s a full-blooded warrior knight on his charger, his face contorted into a rictus of victory celebration which has a strong resemblance to – I think I’ve found our Glyndŵr – Gareth Bale after scoring a goal.

Corwen has a sleepy 1950s quality, which I like. However, we are moving on again, spending a night in Betws-y-Coed. I walk up to Swallow Falls, which are drenchingly impressive, though the entry, via a fortified coin-operated turnstile unworthy of a 1960s football club, is a disgrace. Why is one of Britain’s great natural wonders reduced to this shabby cash cow? The entry is operated by the local council, apparently, but the land belongs to absentee landlords whose ancestors were donated the land by Henry VIII. What would Glyndŵr think?

In March 1401, Glyndŵr’s supporters, faced with tougher barricades at Conwy Castle, managed to grab Conwy fort from the English, and really put the wind up Henry IV. Next day, we head down there, walking the spectacular walls, then dropping down into the enclosed town to visit Plas Mawr, the exquisitely restored Tudor home of the courtier Robert Wynn. This is a real highlight, worth a trip in itself. The quirky L’s Café nearby makes a friendly lunch spot, then after squeezing into a house reputed to be the smallest in Wales, we head for Harlech, the last fortress in Edward I’s formidable ring of iron. With its new visitor centre and arching footbridge, this is now castle-chic, but the real pleasure is still the original dizzying Escheresque complexity and symmetries. We finish with tea and welshcakes in the high street.

Despite capturing Harlech, Glyndŵr’s rebellion petered out. He had failed to team up with Henry “Hotspur” Percy at the Battle of Shrewsbury in 1403 and so missed his great opportunity. (Orson Welles’ forgotten classic Chimes at Midnight brilliantly captures the appalling ferocity of that conflict.) Henry of Monmouth, the future Henry V, burned down Glyndŵr’s homestead at Sycharth, doused the fires of Welsh nationalism and went on to win at Agincourt in 1415, the same year Glyndŵr died. Without the rebellion, Glyndŵr might have been there too, along with the 500 Welsh archers who won the day. Henry had defeated the French, but he never caught Glyndŵr, who spurned all offers of amnesty and disappeared, his grave unlocated to this day.

Shakespeare, however, captured the man perfectly: “That great magician, damned Glendower” at whose birth “the heavens were all on fire, the earth did tremble”. Six centuries later, his trail still lights up the Welsh landscape. But one vital question remains: will Gareth Bale transfer to Hollywood?

• The trip was provided by Visit Wales and Welsh Dragon Tours (01286 831818, ); a four-day Glyndŵr tour costs £599pp (minimum two in party) including driver/guide, B&B in a guesthouse or hotel, and entrance fees

• This article was amended on 17 November 2015. An earlier version misspelled Sycharth as Sycarth.