Grandson of General Montgomery retracing D-Day 4k mile planning journey as he stops at Fratton Park

General Montgomery’s odyssey ahead of D-Day saw him travel 4,000 miles

The grandson of a famous Second World War General is retracing the famous journey he took before D-Day.

Henry Montgomery is following in the footsteps of Field Marshal Bernard Law Montgomery. The General, affectionately known as Monty, was the Commander-in-Chief of the Allied Ground Forces for Operation Overlord in 1944.

Ahead of the Normandy Landings, he undertook a 4,000 mile odyssey across the length and breadth of Britain as part of the preparations. He met with troops, watched training exercises, and visited factories. His actions before and after made him regarded as a national hero.

Henry Montgomery, grandson of Field Marshal Bernard Law Montgomery, is undertaking a a 4,000-mile journey across Britain and Normandy to retrace his WWII steps - including a visit to Fratton Park on Wednesday 29th April 2026.placeholder image
Henry Montgomery, grandson of Field Marshal Bernard Law Montgomery, is undertaking a a 4,000-mile journey across Britain and Normandy to retrace his WWII steps - including a visit to Fratton Park on Wednesday 29th April 2026. | Habibur Rahman
Pictured: Copy picture of Field Marshal Bernard Law Montgomery at Portsmouth Football Clubplaceholder image
Pictured: Copy picture of Field Marshal Bernard Law Montgomery at Portsmouth Football Club | Habibur Rahman

Henry wanted to know more about his grandfather, studying Monty’s diaries written in the run-up to D-Day. He was struck by the scale of journey between April and May 1944. Now, he’s undertaking a mission of his own. Taking him from as south as Normandy and as far as Orkney, Henry will be visiting Second World War veterans and their families to tell the stories of bravery and courage from ordinary people during the war against Nazi Germany.

“To me, Monty was simply my grandfather - a kind, generous, and thoughtful man with a great sense of humour,” Henry said. “My sister and I were given an enormous amount of freedom to play in his garden, particularly in his campaign caravans which were kept in a large shed. Those caravans are now at the Imperial War Museum Duxford, and I think the curators today would be horrified if they knew what we got up to in them.”

The latest leg of Henry’s journey brought him to Fratton Park, as Monty held a fond connection with Portsmouth FC. “I was surprised that my grandfather went to a lot of football matches ahead of D-Day,” Henry said.

“I’m proud of a lot of things my grandfather did. Football was his hobby of passion. He was highly competitive and liked winning, so he would have been supportive of any team he was involved with. Pompey became a team he was deeply involved with. I’m sure he gave the captains advice.”

Pictured: Harold Kempster, Henry Montgomery, Lesley Stephen, Mick Comben and Colin Farmery at Portsmouth Football Clubplaceholder image
Pictured: Harold Kempster, Henry Montgomery, Lesley Stephen, Mick Comben and Colin Farmery at Portsmouth Football Club | Habibur Rahman

Henry’s journey started on April 6 and will finish on June 6. As well as uncovering stories from veterans and families, he’ll also shine a light on those who died while serving, while speaking to children who lived through the war and historians. Some of his conversations will feature in a podcast and documentary series.

The campaign, called Monty’s footsteps, will raise funds to support the British Normandy Memorial’s growing education programme, focusing on teaching young people to understand what happened and why it matters today. Henry’s hoping to raise £1m.

He added: “To my shame it was not until 2014 when I first met veterans from the Normandy Campaign, that I began to realise the significance of D-Day and the Battle that followed. Since then, I have had the privilege of hearing their stories first-hand. Stories of ordinary men and women doing extraordinary things. Thanks to them we, in Western Europe, have enjoyed over 80 years of unprecedented peace and freedom.

“That is being challenged now. It is more important than ever to ensure younger generations learn the cost at which our freedom was bought and are motivated to continue ‘winning the peace’. That is the aim of the Memorial’s educational programme, which I hope will help many people learn this important message at a much younger age than I did.”

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