Chiltern 50 Ultra Challenge

Take on the Chiltern 50 Challenge for Rainbow Trust

Push yourself further in 2026 and join Team Rainbow Trust for an unforgettable challenge through the stunning Chiltern Hills. Walk, jog or run your way through rolling countryside, historic trails and beautiful nature reserves while raising vital funds for families caring for a seriously ill child.

Starting and finishing in Henley-on-Thames, the Chiltern 50 Challenge offers three distances — 10km, 25km or 50km — making it the perfect event whether you’re taking on your first charity challenge or aiming for a major endurance achievement. With full support, fantastic rest stops, a finish-line celebration and breathtaking scenery throughout, this is a challenge you’ll never forget.

About the event

What is the Chiltern 50 Challenge?

Part of the Ultra Challenge series, the Chiltern 50 takes you on a spectacular route through some of the finest countryside in southern England. Expect rolling hills, woodland trails, charming villages and incredible views across the Chilterns Area of Outstanding Natural Beauty.

You can choose from:

• 50km Full Challenge
• 25km Half Challenge
• 10km Challenge

Participants can walk, jog or run at their own pace, either individually or as part of a team.

Route highlights

• Rolling Chiltern Hills countryside
• Woodland and nature reserve trails
• Historic pathways and villages
• Stunning panoramic viewpoints
• Henley Basecamp atmosphere

Included in your challenge

• Fully signed route and GPS tracking
• Covered rest stops every 12.5km
• Free food, drinks and snacks
• Medics, massage teams and support crews
• Medal, finisher’s T-shirt and glass of fizz
• Optional camping and transfer packages

Why support Rainbow Trust?

Helping families through the toughest times

Rainbow Trust Children’s Charity supports families who have a child with a life-threatening or terminal illness. Our expert Family Support Workers provide emotional and practical support tailored to each family’s needs.

Fundraising from the Kent Downs Challenge could help families:

• Get to vital hospital appointments
• Receive support at home
• Help brothers and sisters cope emotionally
• Access practical and emotional support during difficult times

Because no family should face serious childhood illness alone.

Join Team Rainbow Trust

When you sign up with Rainbow Trust, you’ll receive:

• Dedicated fundraising support
• Fundraising ideas and resources
• A Rainbow Trust T-shirt
• Motivation and encouragement from our events team

We’ll support you every step of the way.

Your challenge, your way

Whether you’re completely new to endurance events or an experienced trekker or runner, the Chiltern 50 Challenge is designed for all experience levels. You’ll receive full support from start to finish, helping you achieve something extraordinary while fundraising for Rainbow Trust.

Participants and past challengers praise the event’s supportive atmosphere, scenic but rewarding hills and excellent organisation. Many recommend preparing for repeated hill climbs and changing trail conditions to get the most out of the experience.