The Challenge: 3 Days. 110 Miles. The Cleveland Way.
On 20th August, Simon Whitehead will embark on a three-day charity walk along the full 110 miles of the Cleveland Way in North Yorkshire. Known for its striking scenery and demanding terrain, the Cleveland Way stretches from Helmsley to Filey, taking in heather-clad moorland, steep escarpments, and rugged coastal paths. Attempting the route in just three days is no small feat, with challenging sections such as Sutton Bank’s towering cliffs, the dramatic coastline past Whitby and Scarborough, and countless ascents and descents along the way. Simon’s journey promises to test endurance and determination, all in aid of a cause close to his heart.
Simon Whitehead
Tails, Trails, and Simon Whitehead
To the uninitiated who don’t know who I am, nor what I do, here is a brief introduction into your lives and hopefully, your social feeds as well. My name is Simon Whitehead, and at fifty-seven years of age, I am a well-seasoned rabbit savvy fixer of problems. For several decades I have managed rabbits professionally across the length and breadth of our island, and as such have cross pollinated my clandestine world into the many facets’ of modern media.
Over the years I have adorned every TV channel waxing lyrically about the value of rabbit as a sustainable source of food as a direct result of my organic and chemical free method of rabbit management, ferreting. I have written five books, been in many more, an award-winning filmmaker and write for The Shooting Times magazine about my craft. Not content with this, I also demonstrate in the arena and kitchen at around 25 events each Summer. Due to this nomadic lifestyle, I now live in my big blue van, Bugzy, and although based in the Northeast of England, I spent just as much time travelling or in Suffolk where I used to live. Due to this regimented routine, over the years I have struggled massively with not just my mental health, but a healthy lifestyle as well.
The Challenge – Cleveland Way in 3 days
Six months of being around thousands of people, adrenalin fuelled demos and being the centre of attention to just me working with a dog or two and some ferrets in a blink of an eye. For years I have struggled to come to terms with manic depression, I constantly had anxiety and panic attacks, and as such, have endured a self-taught educational journey into discovering why and how to combat them. More recently, I discovered therapy to teach me how to see signals, avoid toxic traits and people and this is why I have chosen Andysmanclub and The Gamekeepers Welfare Trust as the charities for my walk.
The Cleveland Way is embedded into my heritage. I last did this walk in 2019, a very bitter and sad year for myself personally and to cap it off, I ended up getting injured at the start of day two and had to sit out ¾ of the day before limping on for the final day. This demon has haunted me ever since. This year I am finally going to bury it and complete what I set out to achieve six years ago. It is a huge Challenge. The Cleveland Way in 3 days. 110 miles starting on August 20th at Helmsley. Backed by Alan from Danumb Blades, and supported by the outdoor clothing manufacturers Thrudark, and Brandecosse, I plan to walk around ten hours each day to cover the required distance.
Helping those Who Help
It is for a worthy cause. We all need to understand mental health in the same manner as we do physical health. End the stigma of talking and listening about it, and for this reason I have chosen these two fantastic charities. Since I started to open up publicly about my struggles, I have inadvertently helped others and by walking 110 miles I want to raise not just money but awareness on these subjects.
How To Donate
To hit his target pace of 3.6 mph across brutal, shifting terrain, Simon needed more than just determination, he needed boots that could keep up.
Rugged coastal paths, boggy moorland, jagged rock, the kind of ground that punishes hesitation and weak gear. That’s why Simon laced up his Capriolo Altos. Light on his feet to keep a demanding pace. Low rigidity for percision and connection to the terrain and rugged enough to tackle any conditions he encounters on the trail.
When the miles are relentless and the terrain unforgiving, the Capriolo Alto doesn’t just cope — it thrives.
Step Forward: The Capriolo Alto
Faced with long days at pace across incredibly varied terrain, Simon opted for his trusty Capriolo Altos. With Simon needing to average 3.6 mph to achieve his goal of 110 miles in three 10 hour days, he needed a boot that feels light on his feet, has the flexibility to eat the miles yet provide the protection and support needed to face rugged coastline paths, muddy moorland trails and rocky outcrop. Conditions the Capriol Alto comes into it’s own.
