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Isle of Wight Challenge

Be one of 2,000 adventurers taking on the trek of a lifetime. Hike along spectacular cliffs, past the Needles and up to historic Cowes.

Event details

When: Saturday 2nd May 2026
End: Sunday 3rd May 2026
Activity type: South East, Treks & walks
Full event details

Isle of Wight Challenge at a glance

The full route is a challenging hike covering 106km and more than 1,800 metres of climbing! With eight routes, a two-day option for the full challenge and "Trailblazerz" category for competitive runners, there's an Isle of Wight challenge for every adventurer.

- No minimum sponsorship - raise as much as you can
- Choose from five routes - 10 miles, 25k, 50k, 75k or 100k
- Two-day option for the full route
- Optional camping for the adventurers!

Sign up today

What you'll get

From us:
- support from an experienced fundraising team who can help you reach your goal

From the event provider:
- A fully signed and marked course
- A finisher's medal and t-shirt
- Free food and drink
- A glass of fizz at the finish line

More details about The Isle of Wight Challenge
Arrow doodle
  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 1′
  3. Get in touch with us once you’re done and we will send you a bespoke fundraising pack!
  4. 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!

To see the latest entry fees, please visit the Ultra Challenge website via the link below.

View latest prices and sign up

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, pay in your fundraising.

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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