Chiltern 50 Ultra Challenge

Discover some of the best Chilterns countryside in 2026 and fundraise for Winston’s Wish!

A 50km looped challenge in some of the Chilterns finest countryside, with historic trails, rolling hills, nature reserves, with fantastic views. Join up to 2,000 adventurers and take it on at your pace as a walk, jog, or run – and fundraise for Winston’s Wish! A basecamp in Henley, and a route with real variety and some wonderful scenery – and easily accessible from London.

Sign up 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 25km and 10km options also available – there’s a Chilterns Challenge for everyone! Push yourself further in 2026, take on an Ultra Challenge – the UK’s No.1 Series of treks & trail challenges!

NEW YEAR DEAL! As Winston’s Wish are an official partner on this event, you get over 60% discount on the ‘Full Sponsorship’ registration fee when signing up to support us. Use code HELLO2026 to redeem your discount. 

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 – 10km, 25km, or 50km options
• Walk, jog, or run – it’s your challenge, your way!
• A fully signed route, with a team of ‘Trekmasters’ out on the trail with you
• Regular covered rest stops, with free 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:

• Charity branded top
• Support from our dedicated Sports and Challenges Officer
• Access to training app from our partners GH Training
• Fundraising resources
• Access to our ‘Team Winston’ Facebook group