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Isle of Wight Ultra Challenge

May 2 - May 3

Join us for the Isle of Wight Challenge and take on the island’s costal path!

Great challenges need great settings, and up to 2,000 adventurers will tackle the Isle of Wight’s stunning coastal path over the bank holiday weekend. Take it on at your pace as a walk, jog, or run – and fundraise for Winston’s Wish! It’s along the spectacular southern cliffs, past the Needles, and up to historic Cowes. For Full Island challengers it’s on to Ventnor, and back to our welcome basecamp in Chale after an epic journey!

Join as an individual or as a team; you’ll get full support all the way, plenty of food and drink, optional camping and transfers, a special medal, T shirt and celebration finish. With distance options ranging from the full 106km, down to the ‘Medina 10 mile’ – there’s an Isle of Wight Ultra Challenge for everyone! Push yourself further in 2026, take on an Ultra Challenge – the UK’s No.1 Series of treks and trail challenges.

Click below to sign up on the Ultra Challenge website.

Winston’s Wish and Child Bereavement UK are merging to strengthen the support available for bereaved children, young people, parents and families across the UK. In the coming weeks, Winston’s Wish will change its name to Child Bereavement UK. By taking on the Isle of Wight Ultra Challenge you will still be raising money to support grieving children, young people and families, but the charity you will be fundraising for will be called Child Bereavement UK.

What you’ll get:

  • Sign up from £15
  • Inclusive and fun event with a great atmosphere and camaraderie
  • Choose your distance, including 25km, 50km, 100km PLUS a 10 mile option
  • Walk, jog, or run – it’s your challenge, your way!
  • A fully signed route, with a team of ‘Trek Masters’ out on the trail with you
  • Regular covered rest stops, with free hot food and drink, massages and medics
  • An epic finish line moment, with a glass of fizz, medal and t-shirt
  • Camping, transfer and parking options to make getting there and away easy
  • Full fundraising support, and a choice of fundraising options

What you’ll get from us:

  • A welcome email and fundraising pack
  • A branded top to wear
  • Support from our dedicated team to help you achieve your target
  • Additional fundraising resources upon request
  • Access to training app by our partners at GH Training
  • e-newsletters with news from across the charity