How do I sign up for the Isle of Wight Challenge?

If you’re feeling up to the challenge, register now on the Ultra Challenge website.When you sign up you’ll be asked what sponsorship option you want to choose. Select ‘Option 1′Get in touch with us once you’re done and we will send you a bespoke fundraising pack!Fundraise as much as you can!

I've already signed up - how do I fundraise for Chestnut Tree House?

Thank you for choosing us to donate your sponsorship to – we appreciate every penny.Next steps:Get in touch with us and let us knowWe’ll be in touch with your own bespoke events pack, including fundraising hints and tips and sponsorship form.Once you’ve raised your sponsorship money and completed your event head over to our GoDonate page to donate the money directly to us.

Isle of Wight Challenge

Name: Isle of Wight Challenge
Start: 2025-05-03
End: 2025-05-04

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

When: Saturday 3rd May 2025

End: Sunday 4th May 2025

Activity type: South East, Treks & walks

Full event details

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.

Sign up today

More details about The Isle of Wight Challenge

If you’re feeling up to the challenge, register now on the Ultra Challenge website.
When you sign up you’ll be asked what sponsorship option you want to choose. Select ‘Option 1′
Get in touch with us once you’re done and we will send you a bespoke fundraising pack!
Fundraise as much as you can!

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 £89
Half Challenge (50km): Reg fee £139
Full Challenge (100km): Reg fee £199

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:

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

How your fundraising makes a difference

£54

could pay for a session with a family counsellor, offering emotional support for siblings, parents, and other family members

£119

could pay for a home visit to a child at the end of their life, ensuring they are comfortable and cared for

£184

could give a group of teenagers a rare night out to an accessible cinema, comedy club, or bar accompanied by our Activities Team

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