image of walkers at Isle of Wight

Isle of Wight Challenge

Great challenges need great settings-and none are better than the Island's coastal path. 2,000 adventurers of all experience levels will walk, jog or run.

Event details

Location: Isle of Wight
When: Saturday 29th April 2023
End: Sunday 30th April 2023
Activity type: Treks & walks
Full event details

How to sign up for the Isle of Wight Challenge


If you're feeling up to the challenge, fill in our online form and let us know what event you're interested in.


We'll be in touch with information about your registration options and how to secure your place


We'll help you with your fundraising, send you a sponsorship form, hints and tips and information about us.
To happy trekkers

About the challenge

Along the southern cliffs, past the iconic Needles and onwards in a full island loop. Choose from the full 100km challenge, 50km half-challenge, or even a 25km quarter distance option, with full hospitality & support, including food, drinks and medics

It's along the spectacular southern cliffs, past the iconic Needles and up to historic Cowes at the half way stop. For Full Island challengers it's on to historic Ventnor, and back to our welcome Base Camp in Chale after an epic 106km journey. You'll get full support & hospitality all the way, and with half & quarter Island options also-there's an Isle of Wight Challenge for everyone!

Your entry includes free food and drink at regular rest stops, plus support including medics, marshals and massage. As you cross the finish line, you’ll get a glass of fizz, t-shirt, and a medal to commemorate your achievement.

More details about The Isle of Wight Challenge
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  1. If you’re feeling up to the challenge, register now on the Ultra Challenge website.
  2. When you sign up you’ll be asked what sponsorship option you want to choose. Select ‘Option 2 – Sponsorship for charity’ or ‘Option 3 – Mixed Fundraising for Charity’ if you want to raise money for us.
  3. You’ll have the opportunity to select which charity you’re fundraising for – and you can select Chestnut Tree House under the ‘Other charity’ option.
  4. Get in touch with us once you’re done and we will send you a bespoke fundraising pack!

Charity Sponsorship – you pay a small registration fee, do lots of fundraising and we cover the cost of your event place!

  • Quarter Challenge (25km): Reg fee £15 / fundraising target £250
  • Half Challenge (50km): Reg fee £30 / fundraising target £395
  • Full Challenge (100km): Reg fee £45 / fundraising target £595

Mixed Funding – pay half of the event place cost yourself, fundraise a bit less and we pay the balance of the event place cost.

  • Quarter Challenge (25km): Reg fee £45 / fundraising target £135
  • Half Challenge (50km): Reg fee £72.50 / fundraising target £220
  • Full Challenge (100km): Reg fee £110 / fundraising target £330

Self Fund – you pay the full cost of the event place-fundraise whatever you want, with no set target or deadline, and there’s no cost at all to the charity!

  • Quarter Challenge (25km): Reg fee £79
  • Half Challenge (50km): Reg fee £129
  • Full Challenge (100km): Reg fee £198

You can find details about the race day on the Ultra Challenge website.

If you have a question about trekking and fundraising for Team Chestnut, please contact the Events Team.

Thank you for choosing us to donate your sponsorship to – we appreciate every penny.

Next steps:

  1. Get in touch with us and let us know
  2. We’ll be in touch with your own bespoke events pack, including fundraising hints and tips and sponsorship form.
  3. Once you’ve raised your sponsorship money and completed your event head over to our GoDonate page to donate the money directly to us.

Walking and Trekking guidance

We've put together the best top tips for anyone taking on a charity trek.

Walking information

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