Isle of Wight Ultra Challenge

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.

EARLY BIRD DEAL! As Winston’s Wish are an official partner on this event, you get a 50% discount on the ‘Full Sponsorship’ registration fee when signing up to support us.

Click below to sign up on the Ultra Challenge website.

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 branded Winston’s Wish technical t-shirt
• Charity branded headband
• Support from our dedicated Sports and Challenges Officer
• Fundraising resources
• Access to our ‘Team Winston’ Facebook group