The Tudors' Road to Bosworth Part 1: The Tudors Escape to Brittany

As part of the research for my Tudor trilogy, I decided to follow the journey of Jasper Tudor and his young nephew Henry from Tenby in Wales to their fourteen-year exile in Brittany - and ultimately their return to victory at the pivotal Battle of Bosworth. There are many stories but the documented historical record raises questions and inspired by the travels of Nathen Amin, author of Tudor Wales, I wanted to see for myself what primary evidence I could discover.

Wales had become a dangerous place for the Tudors by 1471. The Lancastrian cause was lost with the news that King Henry had been found dead in his chapel in the Tower of London. The Lancastrian heir to the throne, Edward, Prince of Wales, had been slaughtered in the massacre of Queen Margaret’s forces at Tewkesbury and many Lancastrian nobles were executed by York’s army.

Jasper and Henry found themselves trapped in their stronghold of Pembroke Castle. Their position must have seemed hopeless, particularly when they learned that the men besieging them were fellow Welshmen, loyal to King Edward IV. Then, at the eleventh hour, the siege was broken by a band of Welsh rebels led by Dafydd ap Thomas. It would only be a matter of time before York’s men returned in force, so Jasper and Henry took what might be their only chance to flee to France.

Their problem was that Tenby, the nearest town where they could hope to find a ship, was already taken by the Yorkists. The story which has been handed down over the centuries is that they hid in a cellar belonging to a wine merchant named Thomas White, then escaped to the harbour at night through a secret tunnel.

It was easy enough to find the location of Thomas White’s house in Tenby, as there is a small bronze plaque on the wall outside what is now Boots the Chemists in Tenby High Street. Under a Tudor rose the plaque reads:  By tradition Henry Tudor with his uncle Jasper Tudor Earl of Pembroke was hidden in the cellar on this site before escaping to Brittany in 1471. In 1485 he landed at Dale and defeated Richard III at Bosworth to take the throne as the first Tudor monarch.

In Crackwell Street to the rear of Boots the Tenby Civic Society have also mounted a blue plaque on the wall which reads: It is said that Henry Tudor (Later King Henry VII) escaped through a tunnel here in 1471 when he fled to France.

The manager of Boots kindly agreed to show me the tunnels and we started in the extensive basement cellars, now used as store-rooms. As we entered the tunnels, deep under the street, we were plunged into darkness and had to rely on torches. I saw the roof of the tunnel closest to the entrance had been rebuilt with bricks, and the remains of an ancient fireplace, complete with chimney. This seemed an odd luxury to have in a tunnel and could be further evidence for its use in the past to hide people who might need a fire for warmth. 

Further down the tunnel the roof was roughly hewn through bedrock. This looked to have been done centuries ago, as there was calcification of the surface, which must have taken a long time to form. Unfortunately the tunnel had several exits which were bricked up, but although it wasn’t possible to follow the trail to the harbour, I could see the stories of how the Tudor’s escaped from Tenby could be true.

After emerging back into the bright sunshine I went to pay my respects to the good friend of the Tudors, Thomas White. Visiting the church and looking into his sculpted face reminds me he was a real person, who left his mark on the town and helped change the history of Britain.

The day of the Tudor’s escape doesn’t seem more than five centuries away as I walk from the church in the high street, down the narrow lane with uneven stone steps. I pass the timber-framed Tudor merchant’s house, now a Tudor museum, and see men preparing their boats in the sheltered harbour. It was from here that Jasper and Henry sailed into their long exile, to return to claim the English throne.

I have sailed from this harbour many times, including in complete darkness to catch the tide, just as the Tudors would have done.  There are perilous rocks just below the surface as you head out into the Bristol Channel bound for the equally hazardous Land’s End, which their ship had to navigate before they could even begin heading for the uncertain welcome they might receive in Brittany.

There is a great sense of freedom as you leave the confines of the little town with its narrow streets and pass the monastic island of Caldey before heading out into open water. I can imagine Jasper and Henry Tudor would have stood at the ship’s rail and watched as the last pinpricks of light disappeared from view. They must have felt relieved to escape but also sadness to be leaving their troubled country as refugees, owning only what they could carry and with no idea of when, if ever, they would be able to return.  

In the second part of this journey I chose instead to sail for Brittany from the shorter route of the safe harbour of Portsmouth, passing on the way the bright yellow buoy marking the site of the tragic sinking of a warship belonging to Henry Tudor’s son – the Mary Rose.

Tony Riches

See Also:

The Tudors' Road to Bosworth Part 2: Exiled at Château de l’Hermine, Brittany

The Tudors' Road to Bosworth Part 3: Exiled at Château de Suscinio, Brittany

The Tudors' Road to Bosworth Part 4: Henry Tudor at Forteresse de Largoët, Brittany

The Tudors’ Road to Bosworth Part 5: Jasper Tudor at Château Josselin, Brittany

The Tudors’ Road to Bosworth Part 6: The Tudors Land at Mill Bay in Pembrokeshire

The Tudor’s Road to Bosworth Part 7: The Battle of Bosworth

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